SCHOOL OF CHEMISTRY HONOURS PROJECTS 2020 - MONASH SCIENCE - Monash University
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MONASH
SCIENCE
SCHOOL OF CHEMISTRY
HONOURS PROJECTS
2020
0
Table of Contents
Introduction………………………………………………………………………………………….3
Professor Phil Andrews…………………………………………………………………...…........4
Professor Stuart Batten………………………………………………………………...……........5
Dr Toby Bell…………………………………………………………………………………...........6
Dr Victoria Blair…………………………………………………………………………................7
Professor Alan Chaffee………………………………………………………..…………….........8
Professor Philip Chan …………………………………………………………….…………........9
Professor Perran Cook ………………………………….................………..……………........10
Professor Glen Deacon…………………………………………………………….………........11
Dr Alison Funston…………………………………………………………………………...........12
Associate Professor Mike Grace …………………………………………………………........13
Dr Joel Hooper……………………………………………………………………………..……..14
Professor Cameron Jones…………………………………………………………………........15
Dr Kamila Kochan ……………………………………………………………………………… 16
Professor Tanja Junkers…………………………………………………………………………17
Dr Sara Kyne………………………………………………………………………………………18
Professor David W. Lupton…………………………………………………….........................19
Professor Doug MacFarlane……………………………………………………………….........20
Professor Philip Marriott……………………………………………………………………........21
Associate Professor Lisa Martin…….…………………………………………………….........22
Professor Keith Murray…………………………………………………………………………..23
Associate Professor Ekaterina (Katya) Pas ……………………………………….....…........24
1
Dr Brett Paterson................................................................................................................25
Professor Tony Patti ………………………………………………………………....................26
Dr Chris Ritchie………………………………………………………………............................27
Professor Andrea Robinson ………………………………………………………………........28
Associate Professor Kei Saito……………………………………………………....................29
Dr Alexandr Simonov..........................................................................................................30
Associate Professor Rico Tabor ………………....…………………………………................31
Dr Boon Teo……………………………………………………………………………………… 32
Professor San Thang……………………………………………………………………………..33
Associate Professor Chris Thompson …………………………………………………………34
Associate Professor Kellie Tuck…………………………………………………….................35
Dr David Turner…………………………………………………………………………..............36
Dr Drasko Vidovic………………….……………………………………………………………..37
Professor Bayden Wood…………………………..………………………………....................38
Associate ProfessorJie Zhang……………………………………………………….................39
Dr Angela Ziebell………………….…………………………………………………………….. 40
Industrial Projects
Biofuel Innovations Several Industry Research Project Options…………………………….41
Fire Resistance in Polyisocyanurate Foams for Use in Insulated Panels…………………..43
CSIRO Project
Assessing and validating low cost greenhouse gas sensor technology……………...…44
2
INTRODUCTION - Honours 2020
This booklet is intended to provide an overview of the research activities within the
School of Chemistry and to give you an indication of the Honours projects that will be
offered in 2020. You are encouraged to study these and to speak with the research
supervisors. This research project makes up 75% of the final mark for the Honours year,
with the other 25% from the coursework component which runs in first semester.
Current third year students are eligible to do Chemistry Honours (Clayton) in 2020
provided that they fulfil the entry requirements and that a supervisor is available.
Students will be allocated to supervisors and projects on the basis of their third year
results and their preferred projects. Great care is taken to ensure that all students are
treated equitably and where possible that they are be allocated to the area and
supervisor of their choice.
All Honours candidates must discuss prospective projects with at least four supervisors
before choosing their preferred project. They should then select at least three potential
supervisors and projects in order of preference. The application forms – one for
Honours entry which is an on-line link from the Faculty of Science, the other is the
project nomination form which is from the School of Chemistry – are both available on
the School of Chemistry Honours web page.
Please note that the project descriptions are quite short, and more comprehensive
details can be obtained when speaking to supervisors.
We look forward to seeing you in the Honours course next year. Please contact me if
you have any questions about the Honours year!
Assoc. Prof Mike Grace
Honours Coordinator
Room G25c/19 School of Chemistry, 9905 4078, email: Michael.Grace@monash.edu
3
Professor Phil Andrews
Room No. 121N, Tel: 9905 5509, email: phil.andrews@.monash.edu
This document gives you an idea of the type of research we are undertaking within my group. If
you have any further queries, please do not hesitate to contact me (details above).
More information on my research can be seen at:
http://monash.edu/science/about/schools/chemistry/staff/Andrews.html
1. Combating multi-drug resistant bacteria with metal complexes (Bi vs Fe vs
Ga)
(with Prof. Ross Coppel, Microbiology)
In tackling the continued growth in multi-resistant bacteria and the increasing rate of antibiotic
resistance, this project focuses on the development of bismuth(III) and gallium(III) compounds
which show high activities against common and resistant strains of bacteria (eg MRSA, VRE). Read
more: Chem. Eur. J., 2014, DOI: 10.1002/chem.201404109.
2. Development of new bismuth and gallium based anti-Leishmanial drugs
(with Dr Lukasz Kedzierski, Peter Doherty Institute, University of Melbourne)
Leishmaniasis is a parasitic infection prevalent in the developing world. Current frontline drugs are
based on Sb(V) compounds which show severe side-effects and for which resistance has begun
to appear. This project focuses on developing and testing new bismuth and gallium
compounds as more active and less toxic alternatives. Read more: Dalton Trans., 2018, 47,
971 – 980. DOI: 10.1039/C7DT04171C
3. Developing new antimicrobial materials and coatings
(with Dr. Warren Batchelor, Chemical Engineering; Prof. Laurence Meagher, Monash Institute of
Medical Engineering)
This project investigates the formation of novel bismuth(III) complexes which have high
antimicrobial activity and their incorporation into natural and synthetic polymers and materials.
The antimicrobial activities of the new materials and their potential as ‘clean surfaces’ will be
assessed. Read more: Chem. Eur. J., 2018, 24, 1 – 13. DOI: 10.1002/chem.201801803
4. Targeting Novel Chiral Heterobimetallic Main Group Complexes
(with Dr. Victoria Blair)
This project involves the design, synthesis and full characterization of novel chiral hetero-di-anionic
and hetero-bimetallic complexes of alkali metal, and d or p-block elements (eg. Zn, Cu, Al, Ga, In,
Sn, Sb), and subsequent examination of their reactivity and selectivity in asymmetric synthesis and
in the formation of unusually substituted heterocycles. Requires inert atmosphere handling
techniques. Read more: Organometallics, 2018, 37, 1225–1228.
DOI: 10.1021/acs.organomet.8b00047
5. Heterobimetallic Compounds, Cages and Nanoparticles for Radiation
Sensitisation
(with Dr Melissa Werrett; Prof Leoni.Kunz-Schughart, National Center for Radiation Research in
Oncology, TU-Dresden)
Radiation therapy (RT) is a common form of cancer treatment, however the resistance of tumour
cells to RT is a serious concern. One way to enhance damage to tumour cells is to employ radio-
sensitisers. These are molecules, cages or nanoparticles which can increase the radio-
sensitivity of tumour cells and therefore the effectiveness of the treatment. This project will
explore the design and development of mixed heavy metal compounds and an assessment of
their potential as radio-sensitisers for tumour cell depletion. Background reading: Trends
in Pharmacological Sciences, 2018, 39, 24-48
4
Professor Stuart Batten
Room No. 121C, Building 19, Tel: 9905 4606, email: stuart.batten@monash.edu
This document will give you an idea of the type of research we are undertaking within my group.
If you have any further queries, please do not hesitate to contact me (details above).
More information on my research can be seen at:
http://monash.edu/science/about/schools/chemistry/staff/sbatten/index.html
Coordination Polymers and Supramolecules
We are designing and making coordination polymers (sometimes also known as metal-organic
frameworks, or MOFs) and supramolecular species for a variety of interesting applications,
including adsorption of gases such as hydrogen (for hydrogen fuelled cars) and carbon dioxide
(greenhouse gas capture), long or short range magnetic ordering, molecular switching (for
information storage or molecular sensing), and as new materials for molecular separations. We
are pursuing a number of approaches to this, including:
• New classes of bridging ligands in which the bridging length can be controlled by the
presence or nature of e.g. group I or II metals (Chem. Commun., 2009, 5579).
• Large (3 nm in diameter) spherical
supramolecules (or ‘nanoballs’) (Angew. Chem. Int.
Ed. 2009, 48, 2549 & 8919; ChemPlusChem 2012, 77,
616) which show a large variety of properties. For
example, they can switch between two magnetic spin
states. The change may be induced by change in
temperature or, as a series of experiments in
Bordeaux, France showed, irradiation of light. The
molecular packing also creates cavities within the solid
state, and thus the crystals will readily absorb solvent
vapours, hydrogen, and CO2. Finally, the nanoballs
also show catalytic activity.
• Incorporation of amine groups into porous
MOFs in order to increase the selectivity of CO2
sorption over other gases, such as N2. This is part of a
large multi-institutional program focussed on
developing MOFs for “real world” CO2 capture.
• Porous MOFs for the chromatographic separation of molecules based on size, chirality
or other chemical features. Surprisingly little work has been done in this field, and we are
currently exploring this potential in depth (Chem. Commun. 2014, 50, 3735).
Chemistry of Small Cyano Anions
We have been investigating the chemistry of small cyano anions (Chem. Commun. 2011, 47,
10189). They have shown some remarkable chemistry, including the synthesis of a large range
of transition metal and/or lanthanoid clusters which may have applications as single molecule
magnets, interesting new coordination polymers and discrete complexes showing unusual
packing motifs and ligand binding modes, new hydrogen bonding solid state networks,
nucleophilic addition of alcohols and amines across the nitrile groups to give new anion families,
and the production of ionic liquids containing either the free anions or even metal complexes of
the anions. The versatility and range of applications of these simple anions is unprecedented.
5
Dr Toby Bell
Room G32C, Building 23S, Tel: 69905 4566, email: toby.bell@monash.edu
In the Bell Fluorescence Lab, we apply advanced fluorescence techniques to answer questions in
materials science and cell biology. In most of our research we operate at the ultimate level of resolution
– single molecules – which allows us to detect hidden events and distributions. Application of single
molecule detection allows us to perform super-resolution imaging and break the diffraction limit of light
to reveal previously obscured details, even inside cells.
www.super-resolution.org.au Instagram: Bell_Fluorescence
Visualising cellular remodelling caused by viral proteins:
Viruses have developed all kinds of mechanisms for hijacking cellular
systems for their own needs, as well as for avoiding the immune response.
This project will use super-resolution imaging to examine changes to the
cellular architecture in order to decipher the functions of proteins made by
viruses like Rabies and Hendra. (The image shows microtubules forming
2 μm
large bundles in the presence of rabies P protein)
Deciphering the photophysics of antibody-conjugated fluorophores for bio-imaging:
Alexa and ATTO dyes bound to antibodies are used extensively in biological imaging applications
because of their high specificity and bright, stable fluorescence. Recently, the seconds-long ‘blinking’
of these dyes has been harnessed for super resolution imaging. While the photophysics behind
blinking has been well characterized for individual molecules, this project will investigate the
photophysical interactions available, such as energy funnelling and annihilation, to the clusters of ~4-
6 fluorophores on each antibody.
Investigating DNA damage response in sub-nuclear compartments:
When the cell senses a DNA double strand break, a signaling cascade
involving thousands of proteins is triggered. Recently, a new pathway
within this cascade was discovered to involve recruitment of protein NBS1
to the nucleolus where it affects ribosomal RNA transcription. This project
will use super-resolution imaging to directly visualize the proteins involved
in nucleolar sub-compartments to determine the underlying mechanism
and its interplay with other DNA damage response pathways. (The image
shows Treacle protein ‘puncta’ inside the nucleolus)
Imaging DNA double strand breaks and their repair in cells:
DNA damage is caused by exogenous toxins as well as everyday
replication and transcription. Defects in repair result in serious genetic
diseases and can lead to cancer. However, imaging of damage and repair
inside cells is incredibly difficult because only a few breaks occur at a time.
This project will use multicolor super resolution imaging to focus on these
few breaks and track the temporal interactions involved in their
(mis)repair..
Quantifying orientation in FRET at the single molecule level:
The orientation of the donor and acceptor molecules in energy transfer
(FRET), can efficiency up to a factor of 4, but has never been shown directly
in single molecules. This project will visualize emission dipoles of single
molecules undergoing FRET by using ‘defocused imaging’ of single
molecules and simultaneously measuring FRET efficiency. The defocused
images reveal a molecule’s dipole directly and thus its orientation. (The
image shows defocused patterns for 2 single molecules about 3 microns
apart)
6
Dr Victoria Blair
Room No. 118, Building 23, Tel: 99020907, email: victoria.blair@.monash.edu
This document will give you an idea of the type of research we are undertaking within my group. If you
have any further queries, please do not hesitate to contact me (details above).
P/N heterocyclic scaffold building Advances in Hydrodefluorination
Li‐Br exchange + addition
1,2 addition Li‐Br exchange
Ph
NH O
CO2 CH4
transportation, fossil natural gas systems
H H fuel combustion landfills,
Ph
N
tBu Br
Ph
N
tBu
Ph
N N Ph coal and crude oil agriculture
NO2
HN
Ph HFCs manufacturing,
agriculture
cars 20% of pharmaceuticals and
2 tBuLi semiconductor
R = o‐Br
R’= H hexane, 0˚C
manufacturing
SF6 30% of agrochemicals contain at least
LDA, LDA, TMEDA electrical one C-F bond.
hexane, 0˚C hexane, 0˚C
PFCs transmission
aluminum
R
N production
R = p‐OMe; R’= H
R’
Target imines
OMe
F
H
N 1 Fn Mg(HMDS)2 F F
O N
MeO
R N N
MeO N Ph Fn = 1 Fn = 5 F
R
N hexane, 0˚C hexane, 0˚C N
H3O+ R Si Si
F
N
Li(THF)3 R = CH2SiMe3
N TMP • C‐N bond formation
• CH2SiMe3 addition Na Mg TMP Fn = 5
N
• No cyclisation
OMe
• C‐N bond formation 1 hexane, 0˚C
CH2SiMe3
• No cyclisation
F
F
Ring deprotonation and 1,2 CH2SiMe3 F
addition cascade sequence R • 8‐membered N‐heterocycle
N F
F • CH2SiMe3 group addition
N
• Two C‐N bond formations
R
F
CH2SiMe3 • Cyclisation through ortho site
F
F
R= p-Me, p
-Cl, p
-Br,
p-tBu, p
-OMe , m -Me
What's next……..
• Expand substrate scope
• New method to breakdown harmful F‐
compounds?
S. Orr, E. Border, P. Andrews and V. Blair, Chem. Eur. J., 2019, 25, 11876
• Reaction mechanism probing
Active Metal Catalyst Design Synergistic Metallators
The Allure of Silver
• Superior reactivity
Lewis acidic
metal centre
• Direct Mg‐C bond
L formation
Ag NR 2 • Functional group tolerant
L • Atom economical
stabilising strong
ligand basic site
Substrate Scope
H
Si Ph
O O
Ph
Ph2SiH2 P P O N
R R
H
5 Mol% cat, C6D6,
R R R
R' R.T R'
R = H, alkyl, Ar R = H, alkyl, Ar
Substrate Ph2SiH2 HBpin
Mixed metal deprotonations
Benzaldehyde 94%; t = 1hr 99%; t = 25 mins
Acetophenone 10%; t = 15 hrs 93%; t = 2 hrs N N
NN NN
Na
Trifluoroacetophenone 99%; t = 15 mins 99%; t = 15 mins Na
Na Mg NN
Mg Mg
N
Tertbutylaldehyde 98%; t = 3 hrs 94%; t = 4 hrs NN O
PP Ph
Ph P
• Structure activity relationships
• Hydrofunctionalisation reactions
• Low catalyst loadings 2% mol Direct magnesiations
7
• Stabilising ligand design – NHCs, CACs…
M. Stevens, F. Hashim, E. Gwee, E. Izgorodina, R. Mulvey and V. Blair, Chem. Eur. J., 2018, 24, 15669
Professor Alan Chaffee
Room No. 223N, Building 23, Tel: 9905 4626, email: alan.chaffee@monash.edu
My group undertakes applied chemistry research on topics that are, in some way, related to biomass
and fossil fuel utilization. For example, new approaches to the preparation of industrial chemicals,
specialty liquid fuels (eg, jet fuel), road bitumen, coke for steel making, and specialist high surface
area active carbons are being developed so as to minimize energy losses and CO2 emissions. We
also investigate the capture of CO2 emissions by adsorption and, once captured, its transformation
back into useful products by heterogeneous catalysis. In doing so, innovative new materials such as
mesoporous silicas, metal organic frameworks (MOFs) and ionic liquids (ILs) are employed as
adsorbents, catalysts and/or solvents. These novel materials are often sourced from other research
groups within the School. Molecular modeling tools are also frequently applied in these studies, so
that experiment and theory inform each other. More information on my research can be found at:
http://monash.edu/science/about/schools/chemistry/staff/CHAFFEE.html
Turning Carbon Dioxide into Fuel
Waste CO2, when combined with ‘renewable H2‘ (eg, from
photovoltaic water splitting) over appropriate catalysts, leads to
reduced C1 products (formaldehyde, methanol). Methanol can be
used directly as fuel in petrol engines or be dehydrated to
dimethylether, a diesel fuel substitute. Nanoparticulate catalysts of
varying metal cluster size, supported on high surface area
mesoporous substrates, will be sought that improve reaction rates
and product selectivity.
.
Chemicals from Biomass
This project will make use of CO2, both as
a supercritical fluid in its own right and as
one component of a novel series of
recyclable ionic liquids (known as
DIMCARBs) to selectively extract
discrete chemical classes (phenols,
carboxylic acids, aliphatic or aromatic hydrocarbons, depending on the conditions used) from various
forms of biomass and/or coal. With biomass, this approach offers a renewable alternative to deriving
these fundamental chemical feedstocks that are now mostly supplied from the petroleum industry.
Capturing Carbon Dioxide from Air
Prior work in the group has identified amine-based adsorbents that have the
ability to reversibly capture and release CO2 at concentrations (~15 wt%) and
temperatures typical of the flue gas from power stations. Another approach to
controlling CO2 in the atmosphere could be to adsorb it directly from air at
atmospheric concentration (~400 ppm). This project will prepare and evaluate
new adsorbent formulations for this purpose involving high surface area
mesoporous silica (such as SBA-15) as a support material.
Environmental Applications of Active Carbon Monoliths
The group has recently developed a new form of monolithic carbon that provides for efficient gas
and liquid contact with low pressure drop. These materials have exceptional surface areas and,
therefore, multiple potential applications as adsorbents, catalysts, electrodes,
etc. Their inherent electrically conductive means that they can, in principal, be
very efficiently regenerated by ohmic heating. Projects are available that
investigate their performance for the removal of pollutants from gas phase (e.g.,
NOx) or from liquid phase (e.g., heavy metal) streams, their regenerability, as
well as optimization of fabrication methods.
Active Carbon
Monolith
8
Professor Philip Chan
Room No. 243A, School of Chemistry, Building 23, Tel: 9905 1337, email: phil.chan@monash.edu
R1OCO R 7
We are an organic chemistry group focused on the discovery and R6
[Au]+ (5 mol%)
R7 R6
R4
R5
understanding of new and sustainable reactions through the power of R3
4 Å MS, PhMe R1 OCO R3
TsN R5
homogeneous catalysis and their application to the synthesis of R2 R4
80 °C, 1-17 h N
Ts
R2
24 examples
bioactive natural products and functional materials. More information 40-99% yield
can be obtained from Philip and at:
https://www.monash.edu/science/schools/chemistry/our-
people/staff/professor-philip-wai-hong-chan.
biologically potent TNF- -TNFR1 binding antagonists
(Susanti, D.; Liu, L.-J.; Rao, W.; Lin, S.; Ma, D.-L.; Leung,
Transition Metal Catalysis: New Strategies for Natural C.-H.; Chan, P. W. H. Chem. Eur. J. 2015, 21, 9111)
Products Synthesis and Drug Discovery
Homogeneous transition metal catalysis is one of the most powerful and stereoselective synthetic tools in
the chemist’s armory for the assembly of highly functionalized, architecturally complex molecules from
readily accessible precursors in a single step. For example, a new area in the field of gold catalysis realised
by our group explored the novel reactivities of vinyl gold carbenoid species I as well as those of allenylgold
intermediates II. As part of an ongoing program Previous works:
Selected examples from our group: 1) Angew.
in this area of transition metal catalysis, we will O R 4
3 R O 3 R Chem. Int. Ed. 2008, 47, 1138; 2) Angew. Chem. Int.
4
R
Ed. 2010, 49, 4619; 3) J. Am. Chem. Soc. 2011,
this year focus on the recent new discoveries from R
O2 R 2 O 133 , 15248; 4) J. Am. Chem. Soc. 2012, 134 , 7344;
5) J. Am. Chem. Soc. 2012, 134 , 10811; 6) J. Am.
[Au] R
the lab in photoredox catalysis driven by a R [Au] 1 Chem. Soc. 2013, 135 , 7926; 7) J. Am. Chem. Soc.
1
2015, 137 , 6350; 8) Chem. Eur. J. 2015, 21, 9111;
gold(I,I) complex and sunlight or a blue LED I II 9) Angew. Chem. Int. Ed. 2018, 10.1002/anie.2018-
09376.
source, which is currently a hot topic in research. For 2019:
The goal will be to realise new reactivities, Ph Br
develop new catalysts along the way and provide *[Au -Au ] I I 2+
–
– Br
mechanistic insights into these novel synthetic Ph
technologies. A number of Honours projects that [Au -Au ] I I 2+ [Au -AuBr ] I II 2+
explore this new area of catalysis are available. N
Bn
Key references: see references in the Figure and N
Bn
our reviews: 1) Day, D. P.; Chan, P. W. H. Adv. Ph
Synth. Catal. 2016, 358, 1368; 2) Boyle, J. W.; BrH+
N N
Bn Bn
Zhao, Y.; Chan, P. W. H. Synthesis 2018, 1402. –H +
Organocatalysis: Unleashing the
Enantioselective Potential of Chiral Brønsted Acids
One of the most powerful catalytic methods to
emerge over the last two decades to rapidly achieve
molecular complexity in an enantioselective
manner from readily accessible precursors is
organocatalysis. Our interest in the organocatalytic
reaction chemistry of -rich alcohols is driven by
the ease of substrate preparation providing the
possibility to introduce a wide variety of
substituents. Added to this is the potential
formation of water as the only byproduct that makes
it a highly attractive environmentally sustainable
and atom-economical approach. A recent example
of this strategy is a seminal work by us revealing
Selected examples from our group: 1) J. Org. Chem. 2012, 77, 6937;
the first chiral Brønsted acid catalysed dehydrative
2) Org. Lett. 2016, 18 , 5936; 3) Chem. Asian J. 2017, 12 , 1475; 4) J.
Am. Chem. Soc. 2018, 140 , 5834. Nazarov-type dehydrative electrocyclisation of
aryl- and 2-thiophenyl--amino-2-en-1-ols to 1H-
indenes and 4H-cyclopenta[b]thiophenes. A number of Honours projects that explore this new area of
catalysis are available. Key references: see references in the Figure and our review: Ayers, B. J.; Chan, P.
W. H. Synlett 2015, 1305.
9Associate Professor Perran Cook
Room No. 19/G25a, Tel: 9905 54091, email: perran.cook@.monash.edu
More information on my research can be seen at:
http://monash.edu/science/about/schools/chemistry/staff/cook/
Sand sediments dominate our coastline, yet we have little understanding of how this environment
processes human emissions of nutrients.
Novel metabolic pathways of lipid and hydrogen production in sands
Sands are highly dynamic environments and organisms within this environment must cope with
rapid shifts between oxic and anoxic conditions. We have recently discovered that fermentation
dominates anoxic metabolism in these sediments but the pathways remain unknown. We
hypothesise that a carbon storage mechanism using polyhydroxyalkanoates is taking place. This
project will investigate the pathways of microbial metabolism in sands using a combination of
experiments and metabolite profiling using GC/MS
Figure shows oxygen distribution within a sand ripple. Organisms within this environment must
cope with rapid shifts in oxygen concentrations.
Denitrification in sands
Denitrification is a key reaction in the environment because it removes excess bioavailable
nitrogen. The reaction is typically considered a heterotrophic process where organic carbon acts
as the electron donor.
4NO3- + 5CH2O 2N2 + 4HCO3- + CO2 + 3H2O
Our recent research has discovered that H2 and FeS may also act as electron donors in sand
sediments however the relative importance of these remains unknown. This project will
investigate the importance of H2 and FeS as electron donors for denitrification.
10Professor Glen Deacon
Room No. 136C, Building 19 Tel: 9905 4568, email: glen.deacon@monash.edu
For more information, see: www.chem.monash.edu.au/staff/deacon.html
Rare earth elements (Group 3-Sc, Y, La and the lanthanoids Ce - Lu)
Rare earths are currently seen as the strategic materials of the 21st century with
considerable international concern over the Chinese domination of the supply of
separated elements. Our group provides fundamental knowledge to underpin industrial
developments in the area. Australia has abundant rare earth resources which have
been mainly neglected despite their widespread uses, e.g. ceramic supports for exhaust
emission catalysts, alloy magnets in all car engines, and catalysts for artificial rubber
production. Potential applications include green corrosion inhibitors (below). Their metal-
organic chemistry is a major new frontier and is generating great excitement, for example
in the discovery of new oxidation states. We are particularly interested in high reactivity
rare earth organometallics (Ln-C), organoamides (Ln-NR2) and aryloxides (Ln-OAr), and
have developed unique synthetic methods to obtain them. Features of these compounds
include low coordination numbers and extraordinary reactivity including C-F bond
activation, the most resistant carbon-element bond. To prepare and structurally
characterize the compounds represents a major challenge. The program involves
extensive international collaboration. Some specific projects follow:
1. New Approaches to Metal-Based Syntheses (with Prof. Peter Junk (JCU) and Dr
Victoria Blair)
2. Carbon-fluorine activation with reactive rare earth complexes (with Dr Victoria
Blair and Prof Peter Junk)
3. Heterobimetallic complexes and pseudo solid state synthesis (with Prof. Peter
Junk (JCU) and Dr David Turner)
4. Green Corrosion Inhibitors (with Prof. Peter Junk (JCU), Dr David Turner and Prof.
Maria Forsyth (Deakin University))
5. Platinum Anti-Cancer Drugs (with Prof. Alan Bond, Prof Bayden Wood)
Novel recent structures Techniques
Inert Atmosphere handling; X-ray
crystallography including
Synchrotron use. X-ray powder
diffraction; IR, UV-Vis, NMR
spectroscopy, Mass spectrometry
Pseudo solid state synthesis,
solvothermal synthesis
Project 3 Project 2
Some recent papers
Angew. Chem. Int. Ed., 2009, 48, 1117-1121; Chem. Eur. J., 2009, 15, 5503-5519; Chem. Commun., 2010, 46,
5076-5078; ; Chem. Comm., 2012, 48, 124-126; J. Inorg. Biochem., 2012, 115, 226-239; Chem. Eur. J., 2013, 19,
1410-1420; Organometallics, 2013, 32, 1370-1378; Chem. Eur. J., 2014, 20, 4426-4438; Inorg. Chem., 2014, 53,
2528-2534; Chem. Commun., 2014, 50, 10655-10657; Eur. J. Inorg. Chem., 2015, 1484-1489; Chem.Eur.J., 2016,
22, 160-173; Chem. Eur. J., 2017, 23, 2084-2102; Angew. Chem. Int. Ed., 2017, 56, 8486-8489, Chem.Eur.J., 2018,
24, 17464; Inorg. Chem., 2019, 58, 1912.
11Dr Alison Funston
Room No. G32B, Tel: 9905 6292, email: alison.funston@monash.edu
https://funstongroup.monash.edu/
Description of Project Areas
When matter is divided into tiny, tiny particles, that is, into crystals of nanometer sizes (1 nm = 1
10-9 m), its properties change. We are interested in the changes to the optical properties, or
colour. For example, very tiny spheres containing only 1000’s of gold atoms are red. The colour
of very tiny spheres of CdSe only a few nanometers in diameter can be tuned across the visible
region by changing their size. This effect is due to quantum confinement and the spheres are
called quantum dots (QDs). The colours of nanoparticles can be controlled by:
Changing the size or shape of the crystal
Changing the environment of the crystal
Bringing two or more nanocrystals into close proximity
The nanocrystals have potential applications in nanoscale energy transfer, sensing, colour
responsive coatings for glass, solar photovoltaics and medicine (drug delivery, cancer therapies).
Our research group is part of the ARC Centre of Excellence in Exciton Science. The Centre
researches ways to manipulate the way light energy is absorbed, transported and transformed in
advanced nanoscale materials. The research in the centre aims to find innovative solutions for
renewable energy in:
Solar energy conversion
Energy-efficient lighting and displays
Security labelling and optical sensor platforms
Our research involves synthesis and investigation of the optical properties of nanocrystal systems. We
investigate the mechanism of growth of nanocrystals, making use of electron microscopy (TEM and
SEM). We use dark-field microscopy, fluorescence microscopy, single photon counting and scanning
near-field optical microscopy to determine the optical properties of single nanoparticles and single
nanoparticle superstructures.
Potential honours project titles include:
Controlling the Flow of Energy on the Nanoscale: Investigation of the
control of light (energy) transport through nanoscale structures,
including switching transport on or off, energy and electron transfer
between nanocrystals, across interfaces and within self-assembled
films.
Changing the Colour of Nanoparticles - Nanoparticle Coupling:
Assemblies of nanocrystals have optimal characteristics for many applications. This project aims to
make, understand and use these.
Nanoparticles and Nanowires as Nanoscale Optical Fibres: Nanowires
are able to transport energy below the diffraction limit of light. This
project will investigate how the three-dimensional shape of the nanowire
changes the efficiency of the energy transport.
Growth Mechanism of Nanorods and Nanobars (including
Nanoscale Gold Bullion!): Understanding nanocrystal growth, the
ultimate form of crystal assembly, will allow fine control of the
nanocrystal optical properties – many questions remain
unanswered!
12Associate Professor Mike Grace
Room No. G25c (Water Studies), Tel: 9905 4078, email: michale.grace@monash.edu
These projects can be modified to suit the interests of the student – from physical, analytical
and/or environmental chemistry and biogeochemistry through to aquatic and/or restoration
ecology. A project is available for students who wish to combine synthetic and environmental
chemistry.
Assessing the impacts of pharmaceuticals on aquatic ecosystem processes
Awareness of the effects of common pharmaceuticals on organisms (insects, fish) living in streams and
lakes has slowly emerged over the last decade. Despite their prevalence in urban waterways, there
has been almost no published research on how these pharmaceuticals can affect rates of fundamental
ecosystem processes. Work in our group has shown that some of these chemicals can have dramatic
effects. This project will use novel pharmaceutical diffusing substrates and bioassay techniques to
investigate effects of common drugs like antibiotics, mood modifiers, painkillers and antihistamines on
a range of fundamental ecosystem processes including photosynthesis, respiration, biomass accrual
and denitrification in urban waterways.
Constructed wetlands – environmental benefactors or villains?
This project will examine the extent to which
wetlands around Melbourne generate greenhouse
gases (GHGs) including CH4, N2O and CO2. The
prevailing wisdom is that wetlands must be beneficial
for the environment as they are designed to remove
nutrients and other pollutants from stormwater in
urban creeks. However, previous work in the Water
Studies Centre has shown that under a range of
relatively common conditions, wetlands can also
generate significant quantities of GHGs. This project
will measure rates of GHG production in several
wetlands around Melbourne and develop
understanding of the key wetland characteristics and
conditions that control production. Links with
nitrogen cycling will be explored. Experimental work
will involve field measurements and laboratory
mesocosm (sediment core) investigations.
Developing luminescent probes to determine levels of environmentally relevant ions and
reactive oxygen species with Dr Kellie Tuck
Please see Kellie’s project descriptions for more information. This project is ideally suited to a student
with interests in both synthetic and environmental chemistry.
13Dr Joel F. Hooper
Room No. 242, Building 23 South, Tel: 9902 0482, email: joel.hooper@monash.edu
Our group is focused on the development of new catalytic reactions, using both organic and organometallic
catalysts. We examine novel catalysts and/or new reaction intermediates to develop new chemistry for a variety
of applications.
Catalytic reactions with new metal complexes
We have recently reported the first catalytic application of a monomeric Pd(I) species, in the oxidative cross-
coupling of nucleophiles.1 We are targeting new reaction pathways which make use of this unexplored oxidation
state of palladium.
We are also interested in developing catalytic reactions of ruthenium carbides, a complex with unique reactivity
that has yet to be harnessed in catalysis. This project will access new carbine chemistry using these complexes,
and combine it with established alkene metathesis
chemistry to deliver new organic reactions.
Organocatalytic synthesis of morphine
In a collaboration with the Lupton group,2 we have
developed phosphine catalysed methods for the
construction of 5- and 6-membered nitrogen
heterocycles. In this project, we will
look to develop one of these
reactions for the total synthesis of
morphine and related alkaloids.
Chemical modification of
polymers
We have developed a method for the end-group modification of RAFT polymers, which allows us to attach
functional materials to polymers.3 With collaborators in Monash Medicine, we are developing polymer/antibody
hybrids which will be used to treat disease, with improved stability over natural antibodies.
OH
Me B Me Me
HO
O O O O O O
Ph S Ph Me Me Ph
Me Me Me Me
"Cu"
Ph S Ph Ph
Me Me Me
n n
n
Polymer/antibody hybrid
References: 1) Q. Simpson, M. Sinclair, D. W. Lupton, A. B. Chaplin and J. F. Hooper, Org. Lett., 2018, 20, 5537 2)
J.Ametovski, U. Dutta, L. Burchill, D. Maiti, D. W. Lupton and J. F. Hooper, Chem. Commun. 2017, 53, 13071. 3) H. Golf,
R. O’Shea, C. Braybrook, O. Hutt, D. W. Lupton and J. F. Hooper, Chem. Sci. 2018 doi 10.1039/C8SC01862F
14Professor Cameron Jones
Room No. 1.10, Tel: 9902 0391, email: cameron.jones@monash.edu
Group website: www.monash.edu/science/research-groups/chemistry/jonesgroup
Modern Main Group Chemistry
In the past 10 years remarkable progress has been made in the chemistry of very low oxidation state
and low coordination number s- and p-block compounds. It is now possible to prepare and investigate
the fascinating reactivity of compounds that were thought incapable of existence until a few years ago.
The fundamental and applied aspects of this area are rapidly expanding in the Jones group (see group
website for further details). Representative examples of the many potential Honours projects that are
available within this exciting area are as follows:
(i) Low oxidation state Main Group systems: replacements for transition metal catalysts.
In recent years "trans-bent" compounds containing multiple bonds between two p-block metal(I) centres
have been stabilised by ligation with extremely bulky alkyl or aryl substituents (R). These include the
remarkable heavier group 14 analogues of alkynes, viz. REER (E = Si, Ge, Sn or Pb). In this project
you will prepare examples of related bulky amido substituted "metalynes" (see picture), and related
compounds, and explore their use for the reversible reductive activation of H2, CO2, NH3, ethylene etc.
If this can be achieved, the exciting
possibility exists to use such compounds as
replacements for expensive and toxic
transition metal catalysts in numerous
industrial processes; and for the
conversion of the Greenhouse gas, CO2, to useful
chemical products such as methanol.
see: (i) J. Am. Chem. Soc., 2014, 136, 5283;
(ii) J. Am. Chem. Soc., 2012, 134, 6500; (iii) J. Am. Chem. Soc., 2011, 133, 10074; (iv) Nature, 2010,
463, 171.
(ii) Stabilisation and application of complexes of Group 2 metals in the +1 oxidation state.
It has previously been only possible to prepare compounds
containing the Group 2 metals (Be, Mg or Ca) with the metal in the
+2 oxidation state. Recently, we have reversed this situation with the
landmark preparation of the first thermally stable compounds to
contain Mg-Mg bonds (e.g. see picture). The formal
oxidation state of the magnesium centres in these
compounds is, therefore, +1. As a result, these species are highly
reducing, a situation which has lent them to use, in our
laboratory, as specialist reagents in organic and
organometallic synthetic methodologies. You will further explore
this potential, in addition to examining the possibility of
preparing the first dimeric calcium(I) compounds.
Furthermore, you will examine the use of such systems as soluble
models to study the reversible addition of dihydrogen to magnesium metal (yielding MgH2). This poorly
understood process is of great importance for future hydrogen storage technologies which will be
essential for viable zero emission vehicles powered by fuel cells. The activation of other gaseous small
molecules (e.g. CO2, N2, NH3 etc.) will be investigated at high pressure (ca. 200 atm.) with the aid of
high pressure sapphire NMR tube technology developed in the Ohlin group at Monash.
see (i) Science, 2007, 318, 1754; (ii) J. Am. Chem. Soc., 2015, 137, 8944; (iii) Chem. Sci., 2013, 4,
4383; (iv) Nature Chem., 2010, 2, 865; (v) J. Am. Chem. Soc., 2014, 136, 5283;
15Dr Kamila Kochan
Room No. 1.10, Tel: 9905 1407, email: kamila.kochan@monash.edu
Group website: https://www.monash.edu/science/cfb
Characterisation of Ru-based complexes, novel agents with promising anti-cancerous activity.
From physicochemical properties to interaction with biomolecules.
Recently in the medicinal chemistry metallacarboranes are gaining increasing interest, as they show
promising potential biological activity. In particular, anti-proliferating activity was attributed to
transition metal complex fragments. Combination of these with dicarbollide cluster leads to
development of novel metallodrugs. In this work we focused on the use of [Ru(arene)]2+ groups which
were identified in the last 20 years as promising alternatives to platinum-based anticancer drugs,
demonstrating lower intrinsic toxicity and broad spectrum of biological activity. The novel Ru-
complexes were recently designed and synthetised by a group in Leipzig University (prof. E. Hey-
Hawkins).
The combination of dicarbollide anion with [Ru(arene)]2+ is extremely promising not only due to
potential anti-proliferative activity, but also due to highly hydrophobic properties of dicarbollide. This
can enhance the transport of the metallodrugs through cell membrane and potentially has high robustness
in biological condition, as it is not metabolised by any enzymes. This project focuses on characterising
the properties of several novel Ru-carboranes (examples of structures of some in Fig. 1) using a
computational and experimental approach (IR, Raman, UV-VIS spectroscopy). In particular, we would
like to characterise aspects such as aggregation, dissociation and diffusion mechanisms of selected
ruthenium complexes and examine their interaction with a series of biomolecules.
Figure 1. Structures of selected Ru-based complexes under investigation as potential novel anti-cancer
agents. (Figure adapted from [1]).
Further reading:
[1] Gozzi, M., Schwarze, B., Coburger, P. and Hey-Hawkins, E., 2019. On the Aqueous Solution
Behavior of C-Substituted 3, 1, 2-Ruthenadicarbadodecaboranes. Inorganics, 7(7), p.91.
[2] Gozzi, M., et al. 2017. Antiproliferative activity of (η 6-arene) ruthenacarborane sandwich
complexes against HCT116 and MCF7 cell lines. Dalton Transactions, 46(36), pp.12067-12080.
16Professor Tanja Junkers
Room Nr. 220A, Building 23, Tel: 03 9905 4524, email: tanja.junkers@monash.edu
Group website: www.polymatter.net
The Polymer Reaction Design group strives for the development of
new materials via state of the art polymer synthesis methods. From
fundamentals and kinetics of polymerizations to the design of new
polymer reaction pathways, all elemental steps are addressed and
custom-made materials are constructed. Research spans widely from synthetic chemistry projects over
process design to physical properties of materials.
Core research areas of the PRD group are the synthesis of sequence-defined and sequence-controlled
polymers and oligomers. Such polymers bridge the gap between classical synthetic polymers and
biological polymers such as peptides or RNA. Further, the group focuses on the use of continuous flow
chemistry approaches for the synthesis of complex polymers and for formulation of polymer
(nano)particles. Flow chemistry is an interesting tool that allows us to not only design polymers with
unprecedented accuracy, but also in a simple, and automated fashion. Last, but not least, we are also
working on biopolymers, either biodegradable polymers or materials made from biofeedstocks.
1. Sequence-defined oligomers for biomedical application
Using the well-known RAFT polymerization strategy we design discrete oligomers that mimic peptide
chains. In order to achieve this, amino-acid analogue monomers are first synthesized, followed by
oligomerization and product isolation. Oligomers with encoded information will be obtained and
evaluated for their biological function (antimicrobial, cell guiding). This project is very synthesis oriented
and suitable for more than one student.
2. Automated flow synthesis of polymer material libraries
In the PRD group we have established techniques that allows for synthesis of polymer material libraries
via a self-optimizing autonomous flow reactor. Reactions are fully computer controlled and on the basis
of online-monitoring data, smart algorithms take over the synthesis process and self-optimize for
desired products. We want to extent this system by adding a benchtop NMR spectrometer into the
system. This project is very focused on flow chemistry and process design. Knowledge in computer
programming (Python, LabView) is very beneficial to carry out this project, yet not strictly required.
3. Facing dispersity: How to make discrete polymers and study of their properties
Today, we are able to access a very broad variety of polymer materials, and we come very close to
structure found in nature. Yet, we are still much limited when it comes to dispersity. Via advanced
synthesis and advanced polymer separation we are able to bring polymers towards monodispersity.
This allows us to study these materials from angles that were until today not possible. We will produce
close-to-monodisperse polymers and then study their properties. The project is suited for students with
synthetic interests that also want to work on the physical chemistry side of things.
4. Morphology control in continuous flow micelle formation
Block copolymer micelles are ideal vehicles for targeted drug delivery, but suffer greatly from
reproducibility issues and limited control over the size and shape of the micelles. Flow processes make
the micelle formation more reproducible and scalable. At the same time, flow can be used to beat
thermodynamics and to create micelle morphologies that are otherwise unachievable. We have very
promising results for these procedures and want to investigate the possibilities of flow micelle formation
much deeper. The project will involve synthesis of block copolymers, flow micellation and
characterization of the resulting nanoparticles. This project is cosupervised by Rico Tabor and is
suitable to students who like macromolecular synthesis as much as physical chemistry of nanoparticles.
17Dr Sara Kyne
Chemistry Education and Green Chemistry
Room No. 134B Building 19; Tel: 9905 4555, Email: sara.kyne@.monash.edu
This document will give you an idea of the type of research we are undertaking within my group. If
you have any further queries, please do not hesitate to contact me (details above).
Chemistry education (with Assoc. Prof. Chris Thompson)
Impact of personalising student feedback through Learning Analytics
We are interested in using Learning Analytics to optimise student learning. Learning Analytics
measure and process student data collected from Moodle (the University Learning Management
System). These data allow us to personalise feedback to students, which is particularly difficult in
large student cohorts. We are evaluating how student’s respond to personalised feedback, to inform
us how we can better support students throughout their degree programme.
Green chemistry through context-based learning
We aim to prepare undergraduate students to tackle global challenges confronting modern society.
To achieve this, we are designing and implementing context-based learning activities to encourage
students to make links between chemistry, the environment and society. Our goal is to for students to
learn about fundamental chemistry concepts and relate the concepts to their everyday life, in
particular changing their actions that impact the environment.
Green chemistry synthesis (with University of Groningen, Netherlands)
Green chemistry catalysis
We are developing site-selective catalytic methods to transform simple sugars. These reactions use
photoredox catalysts and visible light to promote carbon-carbon bond formation. The reaction
mechanism is proposed to occur through the coupling of two different radical reactions. We are
investigating the reaction mechanism, and how various radical species and metal intermediates
interact. This is important to inform design of new, site-selective synthetic reactions of more complex
sugars.
R (1.5 equiv)
OH OH
Ir cat. (1 mol%)
O quinuclidine (10 mol%) O
HO HO
HO Bu4NH2PO4 (25 mol%) R
OH OH
OMe DMSO, blue LED, 18 h OH OMe
Iron promoted radical chemistry
We are designing iron based radical reactions for organic synthesis. Previously we found that Fe(I)
and Fe(0) species promote radical reactions under mild conditions. We have investigated the
mechanism of the catalytic cycle and identified key reaction intermediates. With this insight, we are
designing new selective radical reactions and iron-based radical mediators.
18Professor David W. Lupton
Catalysis and Synthesis
Room No. 238 Bld. 23 South; Tel: 9902 0327, email: david.lupton@.monash.edu
My group discovers reactions and uses them assemble materials designed for function. More information
from David or
http://users.monash.edu.au/~dwlupton/index.html
Project A: Enantioselective catalysis with NHC-
catalysis
Organocatalysis has emerged as a powerful approach to
reaction discovery. In 2020 attention is centered on three
reactive intermediates (enediamine A, and enetriamine
B, and dienyl acyl azolium C) accessible using NHC
catalysts.1 Specifically their capacity to enable novel
enantioselective transformations will be examined. A
number of honours projects broadly based on this topic
are available. Key references: 1) Nguyen X. B; Nakano Y.; Duggan,
N. M.; Scott, L.; Breugst, M.; Lupton, D. W. Angew. Chem. Int. Ed. 2019, DOI: 10.1002/ange.201905475; Fernando, J. E. M.; Nakano,
Y.; Lupton, D. W. Angew. Chem. Int. Ed. 2019, 53, 2905; Gillard, R.; Fernando, J. E. M.; Lupton, D. W. Angew. Chem. Int. Ed.2018, 57,
4712.
Project B: Hybrid Biocatalysis
Recently we commenced studies in collaboration with Professor Jackson (ANU) on the discovery of
chemical reactions using a new type of biocatalysis in which both the protein and the cofactors (THDP)
are modified to allow optimal performance. In this project we will prepare a series of new co-factors
(THDP) and examine their use firstly as organic catalysts and then with wild type enzymes, which will
then be modified using directed evolution approaches2 to give new hybrid biocatalysts.3 A flow chart
describing this project is shown below, with section 1 and 2 conducted at Monash; 3 in collaboration.
Key
references: 2) For reviews see: Kan, S. B. J., Lewis, R. D., Chen, K. & Arnold, F. H. Science 2016, 354, 1048. 3) Campbell, E. C. Grant,
J.; Wang, Y.; Sandhu, M.; Williams, R. J.; Nisbet, D. R.; Perriman, A. W.; Lupton, D. W.; Jackson, C. J. Adv. Biosystems 2018, 2, 1700240.
Project C: Structural Modification of linozelid antibiotics.
Obtaining structural information of biological materials using X-ray analysis can be challenging. Using cryo-
EM approaches the structure of the ribosome with antibiotics bound
have been obtained. Using this data we have developed new
antibiotics.4 Having obtained recent proof of principle for this
approach, we will complete a rigorous analysis of linozelid (and
related structures) guided by cryo-EM in 2020. (Colaboration: Dr
Belousoff, Microbiology) Key references: 4) Belousoff, M. J.; Venugopal, H.;
Wright, A.; Seoner, S.; Stuart, I.; Stubenrauch, C.;
Bamert, R. S.; Lupton, D. W. Lithgow
T. ChemMedChem 2019, 14, 527
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