May 2012 - csacs - McGill University

CSACS 10 th Annual
Meeting
9 - 10 May, 2012
Concordia University, Montreal
Centre for Self Assembled Chemical Structures
Centre de Recherche sur les Matériaux Auto-Assemblés

Table of Contents
Table of Contents 3
Organizing Committee 4
Program at a Glance 5
Lectures : Keynote Speakers 7
Oral Presentations 9
Poster Exhibition 19
3

Special thanks to/Remerciements:
CSACS Coordinator:
Petr Fiurasek
CSACS Student Committee President:
Andrea Greschner (McGill University)
Webpage Administrator:
Rolf Schmidt (Concordia University)
Graphics Design and Booklet:
Mohidus Samad Khan (McGill University)
CSACS Student Committee:
Gwenaelle Bazin (University of Montreal)
André Besette (University of Montreal)
Olga Borozenko (University of Montreal)
Karina Carneiro (McGill University)
Amined Fourati (University of Montreal)
Alexis Goulet-Hanssens (McGill University)
Zahid Mahimwalla (McGill University)
Georgios Rizis (McGill University)
Jean François Wehrung (University of Sherbrooke)
4

May 9, 2012
PROGRAM AT A GLANCE
9:00-10:00: Registration, refreshments & poster setup
10:00-10:05: Opening remarks
10:05-10:50: Bruce Lennox
Still Self-Assembling After All These Years
10:50-11:35: Mark MacLachlan
All Twisted Up: New Materials with Unusual Pores
11:35-12:00: Jaclyn Brusso
Functionalized Thienoacenes: Enhancing π-π Interactions
Through Expansion of the π-Conjugated Framework
12:00-13:00: Lunch
13:00-13:45: Jim Wuest
13:45-14:10: Linda Reven
Nanoparticles in Liquid Crystals: History of a CSACS-
CRMAA Collaboration
14:10-17:40: Poster session
18:00-19:00: Reception at the Holiday Inn Midtown
19:00: Gala dinner
5

May 10, 2012
9:30-10:00: Coffee and refreshments
10:00-10:05: Opening remarks
10:05-10:50: Leonard MacGillvray
Crystal Engineering the Covalent Bond: Self-Assembly
Required
10:50-11:35: Graeme Day
Crystal structure prediction: an emerging method in crystal
engineering
11:35-12:00: Oleksandr Ivasenko
Supramolecular chemistry in 2D: host-guest systems based
on self-assembly of trimesic acid
12:00-13:00: Lunch
13:00-13:45: Peter Grutter
Using AFM techniques to measure properties of nanoscale
and molecular scale systems
13:45-14:10: Cecile Malardier-Jugroot
Confinement effect in polymeric nanotemplates
14:10-14:55: Mario Leclerc
Conjugated Polymers from Micro-Electronics to Genomics
14:55-15:15: Closing remarks & announcement of the poster winners
15:15-16:00: Member meeting
6

Lectures

8
Lectures
Crystal structure prediction: an emerging method in crystal engineering
Oleksandr Ivasenko, Catholic University Leuven
Nowadays, nanotechnology as a study of manipulation of properties and
behavior of matter at the atomic and molecular levels attracts significant
interest in both fundamental studies and industrial applications. Our
abilities to design, control and utilize nanomaterials rely on profound
understanding of often complex interplay between various intermolecular
interactions. Lowering dimensionality of the system from 3D (e.g. crystals
and thin films) to 2D (monolayers) significantly simplifies the analysis and
improves the control over intermolecular interactions. In this regard,
investigation of molecular self-assembly on atomically flat substrates
represents convenient test-bed suitable for probing new supramolecular
designs and organization of molecular components via appropriate
scanning probe microscopy. In this work I will present results of scanning
tunneling microscopy investigation of a series of host-guest systems based
on surface self-assembly of trimesic acid.

Lectures
Still Self-Assembling After All These Years
Bruce Lennox, Department of Chemistry, McGill University
Self assembly has been the common theme of all of my research for the
last 33 years- with the focus on lipids, block copolymers, and surfactants.
The structures resulting from application of the rules of self assembly are
not only fascinating in themselves, but often lead to fascinating
applications.
Some recent examples of our use of self assembly to address problems in
nanomaterial syntheses (A), designed interfaces (B), and neurosciences (C)
will be discussed.

10
Lectures
Using AFM techniques to measure properties of nanoscale and molecular
scale systems
Peter Grutter, Department of Physics, McGill University
Atomic Force Microscopy (AFM) is a technique that allows atomic scale
spatial resolution on essentially any material, including insulators and
metals, in essentially any environment ranging from ultra high vacuum to
liquids. In addition, many properties, such as surface potential, stress,
adhesion or friction can be measured at the same length scale. In this
presentation I will give an overview over some of the properties
measurable relevant to understanding molecules on surfaces. I will
concentrate on 3 topics:
1. AFM can be used to measure the ground state and excited state
energy levels of quantum dots, and possibly molecules, by
understanding dissipation of the AFM cantilever. AFM techniques can
also be used to measure variations in the surface potential on
semiconductors and oxide surfaces. We discovered large variation of
the surface potential (~250 mV) on length scales of 50nm. Such large
potential variations are expected to strongly affect the operation of
nanoscale electronic systems or possibly even adsorption of
molecular species.
2. We have used UHV AFM to understand and control the nucleation
and growth of molecules on insulating surfaces. We can generate
different molecular packing structures by suitable templating of the
insulating substrates. This then allows us to correlate optical
properties with structure using Kelvin Probe Force Microscopy,
including molecular systems relevant to organic photovoltaics (OPV).
Preliminary results indicate that we can observe exciton formation in
model OPV systems.

Lectures
3. Finally, I will show that AFM force spectroscopy in electrochemical
and liquid environments can observe liquid layering effects with
atomic resolution close to the surface.

12
Lectures
Crystal structure prediction: an emerging method in crystal engineering
Graeme Day, Department of Chemistry, University of Cambridge
Ab initio crystal structure prediction has been a long-term goal in the field
of computational chemistry and has fuelled the development of methods
for modeling the crystal structures of organic molecules. The principal
method used for crystal structure prediction is based on global searches of
the lattice energy surface. Recent years have seen significant progress
towards reliable crystal structure prediction methods for small molecules.
The main target application of these methods has been as a tool to inform
solid form selection for pharmaceutical materials, which has motivated
the developments necessary to tackle more complex systems:
conformationally flexible molecules and multi-component materials, such
as cocrystals, salts and solvates.
This presentation will give an overview of recent progress in this field, the
challenges involved in developing reliable crystal structure prediction
methods, and the current state of this area of research. A forward-looking
view will also be discussed of broader uses of these methods as a general
tool for guiding crystal engineering studies aimed at the design and
discovery of materials with targeted properties using, as an example, the
development of microporous molecular crystals.

Lectures
Conjugated Polymers from Micro-Electronics to Genomics
Mario Leclerc, Département de Chimie, Université Laval
Conjugated polymers have received a lot of attention since they combine
the best features of metals or semiconductors with those of synthetic
polymers. For instance, solar cells based on poly(2,7-carbazole) and
poly(thienopyrroledione) derivatives have revealed power conversion
efficiencies up to 8 %. This class of materials could lead to printable and
flexible photovoltaic devices as well as other plastic electronic devices.
Moreover, we will describe novel synthetic methodologies for a simple
and 'green' preparation of known and unknown well-defined conjugated
polymers. Finally, we will present a new optical detection mechanism
based on electrostatic interactions between a cationic polythiophene
derivative and negatively-charged oligonucleotides. This method could
make possible the rapid assessment of the identity of single nucleotide
polymorphisms (SNPs), genes, and pathogens.

Nanoparticles in Liquid Crystals: History of a CSACS-CRMAA
Collaboration
Linda Reven, Department of Chemistry, McGill University
14
Lectures
Current research in my group was motivated by the formation of CSACS-
CRMAA ten years ago. The story of this research mirrors the evolution of
the Centre in terms of new members, research associates, equipment and
research directions. Nanoparticles with mesogenic groups reversibly selfassemble
in liquid crystal matrices at the phase transitions to form micron
scale periodic structures over macroscopic areas. The synthetic,
characterization and theoretical collaborations behind this ongoing project
will be described.

Lectures
Confinement effect in polymeric nanotemplates
Cecile Malardier-Jugroot, Department of Chemistry and Chemical
Engineering, Royal Military College of Canada, Kingston
The most efficient catalysts have been developed and optimized by living
systems. Indeed, in vivo enzyme-catalyzed reactions are several orders of
magnitude more efficient than platinum based catalyzed reactions.
However, the rate of reaction and equilibrium interactions are
considerably reduced when the biological systems are studied in vitro. This
phenomenon is largely attributed to the effect of confinement or
macromolecular crowding present in the cell. Confinement can also be
observed in an aqueous solution containing surfactants (amphiphilic
copolymers).
The hollow nanoarchitectures obtained by self-assembly is used as a
model template to study confinement within a soft shell system. The
paper will present the characterization of polymeric nanotemplates with
1-dimensional (nanotubes) or 2-dimensional (nanosheets) and the effect
of confinement on reaction rates within the nanotemplates. The study
showed that the combination of experiment and molecular modelling
techniques gives a clear and precise characterization of the effect of
confinement in soft nanotemplates.

Crystal Engineering the Covalent Bond: Self-Assembly Required
Leonard R. MacGillivray, Department of Chemistry, University of Iowa
16
Lectures
Noncovalent and covalent bonds are central to chemistry and life's
processes. The former are exploited in supramolecular chemistry for the
construction of assemblies of molecules that exhibit properties and
function beyond individual components. The latter lie at the core of our
understanding of the structures and properties of molecules. Nature
combines noncovalent and covalent bonds to sustain life's processes. The
synthesis of proteins, for example, requires a molecular code to be
translated and transcribed via the formation and breakage of noncovalent
(e.g. hydrogen bonds) and covalent bonds (e.g. peptide bonds). The
fidelity and generally with which Nature combines noncovalent and
covalent bonds continues to inspire chemists to mimic such processes for
the design of new catalysts, molecular machines and devices, and new
forms of medicine.
In this presentation, a method being developed in our laboratory that
enables noncovalent bonds to be utilized, in a general way, to direct the
formation of covalent bonds will be described. We show how small
organic molecules and inorganic complexes act as templates to direct
photochemically induced [2+2] cycloaddition reactions in the solid state.
We demonstrate how the method enables molecules to be generated
stereospecifically, in quantitative yield, and gram amounts. The relevance
of this method to the fields of chemical synthesis, green chemistry, and
molecular nanotechnology will be discussed. Related work in the fields of
organic semiconductor and pharmaceutics will also be presented.

Lectures

All Twisted Up: New Materials with Unusual Pores
Mark MacLachlan, Department of Chemistry, University of British
Columbia
18
Lectures
Mesoporous materials, which have pores ranging from 2-50 nm in
diameter, are attractive for many potential applications including drug
delivery, environmental remediation, gas storage, and catalysis. In 1992,
Kresge et al. described a new supramolecular templating method for the
synthesis of mesoporous silicates wherein a silica precursor is hydrolyzed
in the presence of a self-assembled (liquid crystalline) ionic surfactant
template. 1 Since 1992, liquid crystal templating has been used to make
diverse mesostructured and mesoporous materials with lamellar,
hexagonal and cubic structures, and a broad range of compositions. Also,
the pore sizes can be easily controlled with appropriate choice of ionic,
non-ionic, or polymeric surfactant. Chiral mesoporous materials can be
prepared using chiral surfactant templates. 2 Efforts to create mesoporous
materials that have a chiral nematic structure have been met with limited
success, although such materials may have interesting and attractive
properties. 3
In this presentation, I will describe our recent work to create and
understand new mesoporous materials with chiral nematic ordering. Using
nanocrystals of cellulose as a supramolecular template, we have prepared
thin films of silica 4 and carbon 5 that have chiral nematic organization.
1. C.T. Kresge, M.E. Leonowicz, W.J. Roth, J.C. Vartuli, J.S. Beck Nature
1992, 359, 710.
2. S. Che, Z. Liu, T. Ohsuna, K. Sakamoto, O. Terasaki, T. Tatsumi, Nature
2004, 429, 281.
3. a) A. Thomas, M. Antonietti, Adv. Funct. Mater. 2003, 13, 763. b) E.
Dujardin, M. Blaseby, S. Mann, J. Mater. Chem. 2003, 13, 696.

Lectures
4. K.E. Shopsowitz, H. Qi, W.Y. Hamad, M.J. MacLachlan, Nature 2010,
468, 422.
5. K.E. Shopsowitz, W.Y. Hamad, M.J. MacLachlan, Angew. Chem. Int.
Ed. 2011, 50, 10991.

Functionalized Thienoacenes: Enhancing π-π Interactions Through
Expansion of the π-Conjugated Framework
Jaclyn Brusso, Department of Chemistry, University of Ottawa
20
Lectures
Organic semiconductors (OSCs) have seen considerable development over
the past two decades owing to their potential use in next-generation
electronic devices. Since the performance of electronic devices critically
depends on the extent of molecular order (in addition to other factors),
rational engineering of self-organizing molecular systems with
multifunctional characteristics is essential to the continuation of these
advancements. To that end, we aim to develop molecular architectures in
which donors and acceptors are covalently linked thereby providing an
approach to achieve dimensional control over phase separation at the
nanoscale. Furthermore, extension of conjugation, in multiple directions
via a multidentate aromatic core, should provide enhanced π-π
interactions and lead to high charge carrier mobilities. As a starting point,
we recently prepared a series of materials in which oligothiophenes are
covalently linked to a central benzenic (1) or tetrathienoanthracene (2)
core. The synthesis and characterization of these materials will be
presented.

Posters

01: Model lipid membranes for evaluating specific cellular responses
Carolin Madwar, McGill University (Bruce Lennox)
22
Posters
02: Mirror Symmetry Breaking and Chiral Amplification in Conglomerate
Crystalline Systems
Dylan McLaughlin, Concordia University (Louis Cuccia)
03: High-sensitivity immunoassay using silver enhancement
Gina Zhou, McGill University (David Juncker)
04: Facile Synthesis and Characterization of Fluorescent Nanocrystalline
Cellulose
Rakesh Singh, McGill University (Mark Andrews)
05: Solvent-free synthesis of molecules based on reversible bonds
Neil Macdonald, McGill University (Tomislav Friscic)
06: Solvent-free and low-energy assembly of metal-organic materials in
the solid state
Cristina Mottillo, McGill University (Tomislav Friscic)
07: Inorganic Hetero-poly-metallic Structures: From Building Blocks to
Assemblies
Elodie Rousset, Université de Montréal (Garry S. Hanan)
08: Methacrylate Derivatives of Bile Acids: New Monomers for Dental
Resins
Kun Zhang, University of Montreal (Julian X. Zhu)

Posters
09: Dip-coating regimes observed with supramolecular diblock
copolymer thin films
Sébastien Roland, University of Montreal (Robert E. Prud'homme)
10: Crystalline colloidal arrays made of stimuli-responsive core-shell
microspheres
Gwénaëlle Bazin, University of Montreal (Julian X. Zhu)
11: Synthesis of self-assembled monolayer to promote or reduce
adsoprtion of biomolecules contained in complex biological fluids
Julien Breault-Turcot, University of Montreal (Jean-François Masson)
12: The Effects of Conjugation: New Thiophene-Based Electrochromic
Molecules
Sophie Bishop, University of Montreal (William Skene)
13: Photoswitchable Polyelectrolyte Multilayers: Towards Directed Cell
Growth
Alex Goulet-Hanssens, McGill University (Christopher J. Barrett)
14: Cetylpyridinium chloride ability to adhere to Streptococcus mutans
biofilms is conserved upon its incorporation in liposomes.
Nicolas Cottenye, Université de Montréal (Michel Lafleur)
15: Facile synthesis of hydroxyformamidines by N-oxidation and their
complexation with transition metal ions
Pierre Long Nguyen, University of Montreal (Garry S. Hanan)
23

POSTER 16: Nanofibrillated cellulose gel microrheology
Leila Jowkarderis, McGill University (Reghan Hill)
17: Nanofibrillar cellulose synthesis and its deposition on paper-based
substrates
Salman Safarimohsenabad, McGill University (Reghan Hill)
18: NIR Light-Responsive Polymer Micells and Hydrogels Using
Upconverting Nanoparticles
Bin Yan, University of Sherbrooke (Yue Zhao)
19: Packing of Twisted and Non-Twisted Cellulose Chains into Crystals
Kevin Conley, McGill University (Theo G.M. van de Ven)
20: Gold Nanoparticles in Liquid Crystal: Synthesis, Assembly and
Simulation
Jonathan Milette, McGill University (Linda Reven)
21: Phase separation in model stratum corneum lipid mixtures
Robert Poulin, University of Montreal (Michel Lafleur)
24
Posters
22: Towards a Field-Deployable SERS-Based Energetic Material Sensor for
Water Quality Monitoring.
Debby Correia Ledo, Université de Montréal (Jean-François Masson)
23: Nematic Liquid Crystals: From Disclination Lines to Elastic Properties
Alireza Shams, McGill University (Alejandro D. Rey)

Posters
24: Monitoring methotrexate in clinical samples of cancer patients
during chemotherapy with a SPR sensor
Sandy Shuo Zhao, University of Montreal (Jean-François Masson)
25: The effect of synthetic vertices and DNA-to-vertex connectivity on
the stability and assembly of self-assembled DNA nanostructures
Andrea Greschner, McGill University (Hanadi Sleiman)
26: Synthesis of phenolic surfactants for the fabrication of functional thin
films with biocompatibility
Arison Rajasingam, Concordia University (Christine E. DeWolf)
27: New lipidic membranes to better predict permeability of orally
administered drugs.
Nirasay Souryvanh, University of Montreal (Antonella Badia)
28: Three Dimensional ‘DNA-minimal’ Scaffolds: Assembly, Organization
of Block Copolymers and Cellular Uptake Studies
Chris McLaughlin, McGill University (Hanadi Sleiman)
29: Substrate dependence in molecular self-assembly: nanomeshes on
Cu and Ag(111)
Laurentiu Eugeniu Dinca, INRS Varennes (Federico Rosei)
30: Stimuli-Responsive Polymer Brushes: From Controlled Release to
Switchable Protein Binding
Surjith Kumar, University of Sherbrooke (Yue Zhao)
25

31: Self-assembling bile acid-PEG conjugates
Satu Strandman, University of Montreal (Julian X. Zhu)
26
Posters
32: Density Functional Theory Studies of Hexanethiols Packing density on
Gold Surfaces (001)
Hang Hu, McGill University (Alejandro D. Rey)
33: Formation of Cationic Non Phospholipid Liposomes with
Monoalkylated Primary Amine and Cholesterol
Zhongkai Cui, University of Montreal (Michel Lafleur)
34: Self-assembly of oligothiophenecarboxylic acid monolayer by
Scanning Tunneling Microscope
Chaoying Fu, McGill University (Dmitrii F. Perepichka)
35: Novel Sulfanyl and Sulfonyl Substituted Low Band Gap
Thienothiophene Polymers and their Device Performance.
Julia Schneider, McGill University (Dmitrii F. Perepichka)
36: Block Random Copolymers of N-alkyl-substituted Acrylamides with
Double Thermosensitivity
Mohammadtaghi Savoji, University of Montreal (Julian X. Zhu)
37: Synthesis and characterization of thiophene and triphenylamine
based polymers in solid state
Lambert Sicard, Université de Montréal (William Skene)

Posters
38: Self-Emulsifying Drud Delivery Systems (SEDDS) Based on PEGylated
Bile Acids to Improve the Solubility and the Bioavailability of
Itraconazole
Frantz Le Dévédec, Université de Montréal (Julian X. Zhu)
39: Scanning Probe Microscopy (SPM) At The Laboratory of
Characterization Of Materials (LCM)
Patricia Moraille, Université de Montréal (Antonella Badia)
40: Membrane Disruption Mechanism of a Novel Antimicrobial Peptide –
GL13K
Vinod Balhara, Concordia University (Christine E. DeWolf)
41: Fate of the Bridged Multi-Chromophore Complexes during Hydrogen
Production
Daniel Chartrand, University of Montreal (Garry S. Hanan)
42: π – Conjugated Fluorescent Polyazomethine Copolymers: Synthesis,
Characterization and Halochromic Properties
Satyananda Barik, University of Montreal (William Skene)
43: 2D π-Conjugated polymers
Luis Cardenas, INRS Varennes (Federico Rosei)
44: Synthesis, Optoelectronic Properties and Electrochromic devices of
2,5-Bis(3-phenylallylideneamino)thiophene Derivatives
Daminda Navarathne, University of Montreal (William Skene)
27

45: Formation of Gold Nanoparticle Networks Using Dual-Affinity
Peptides
Julia Del Re, McGill University (Amy Blum)
46: Fluorene-Azomethines Automer -Synthesis-
Florent Bonnefond, University of Montreal (William Skene)
47: Functionalized colloidal microspheres at soft interfaces
Amir Sheikhi, McGill University (Reghan Hill)
28
Posters
48: Using Azadipyrromethene Dye Derivative in Coordination Chemistry:
Homoleptic M(II) Complexes
André Bessette, Université de Montréal (Garry S. Hanan)
49: A Novel Approach to the Formation of Tobacco Mosaic Virus-like
Rods
Josh Lucate, McGill University (Amy Blum)
50: Control of block copolymer aggregate morphologies for
poly(ethylene oxide)-block-polycaprolactone in an aqueous environment
Georgios Rizis, McGill University (Theo G.M. van de Ven)
51: Effect of the monolayer film composition on the redox actuation of
microcantilevers functionalized with ferrocenylalkanethiolates
Eric Dionne, University of Montreal (Antonella Badia)

Posters
52: Self-assembly and metal coordination of 2,5-bis(octadecylamino)-pbenzoquinone
(C18p) and 4,6-bis(octadecylamino)-m-benzoquinone
(C18m) at the solid-liquid interface – An STM investigation
Yuan Fang, Concordia University (Louis A. Cuccia)
53: Polyacrylic Acid Brushes: Real-time Degrafting Studies - Effect of pH
and Salt Concentration
Olga Borozenko, University of Montreal (Suzanne Giasson)
54: Studies of Push-Pull Star-shaped Conjugated compounds of
Azomethines Derived from Triphenylamine
Thomas Skalski, Université de Montréal (William Skene)
55: All-fluorene azomethines copolymers: synthesis and opto-electronic
properties
Charlotte Mallet, Université de Montréal (William Skene)
56: Fluorescent Polymer-Enabled Observation of the Self-Assembly of
Lipids on Nanoparticle Surfaces: A Single Particle Study
Christina Calver, McGill University (Gonzalo Cosa)
57: Fluorescence Quenching of Cy3-Labeled DNA Duplex by Divalent
Transition Metal Ions: A Single Molecule Study
Viktorija Glembockyte, McGill University (Gonzalo Cosa)
58: Self-Assembled Macromolecules Based Platform for Applications in
Biology
Anjali Sharma, McGill University (Ashok Kakkar)
29

POSTER 59: Developing multimodal probes for biomedical application
Tina Lam, McGill University (Ashok Kakkar)
30
Posters
60: Self-assembled complexes constructed through one pot combination
of Pd(II), TMEDA and pyridine based ligands
Sreenivasulu Bandi, University of Montreal (Garry S. Hanan)
61: Visualizing the formation and exploring the structure and dynamics
of DNA Nano- architectures. A single molecule study.
Amani Hariri, Université McGill (Gonzalo Cosa)