CSACS Bulletin du CRMAA

Centre de recherche sur les matériaux auto-assemblés Centre for self-assembled chemical structures Février 2017 February Volume 83

Visit: McGill (Feb. 21)/INRS (Feb. 22)/Sherbrooke (Feb.23)

Titre: Transformation et applications activées par Organoboron

Title: Organoboron Enabled Transformation and Applications

Résumé/Abstract:

Organoboron compounds have at-

tracted much recent research attention due

to their unique electronic properties and

versatile applications. During the course of

our investigation on boron-based lumines-

cent materials, we discovered unprecedent-

ed photochromism involving structural

transformation of the boron core and re-

versible C-C bond formation/breaking me-

diated by the boron atom. We have estab-

lished that both electronic and steric factors

play an important role in this unusual struc-

tural transformation. Further investigation

on photo-responsive behavior of boron com-

pounds led to the discovery of previously un-

known photoelimination reactions of organoboron molecules, which pro-

vides a convenient means for achieving B,N-doped arenes. As observed in

photochromic boron systems, electronic and

steric factors were found to dictate the reac-

tion pathways and the quantum efficiencies of

photoelimination reactions. These findings

provide valuable insights on photoreactivity of

boron compounds and design principles for

new photo-responsive organoboron com-

pounds.

Table des matières:

Séminaire: Prof. Wang p.1

Séminaire: Prof. Lessard p.2

Bourse FRQNT Internationale: McTaggart et Church p.3

Programme d'échanges hors Québec de pro-fesseurs: Gal-lagher et Rosei p.4

Publications p.5

Table of contents:

Seminar: Prof. Wang p.1

Seminar: Prof. Lessard p.2

International FRQNT Intern-ship: McTaggart and Church p.3

FRQNT scientist-in-residence program: Gal-lagher and Rosei p.4

Publications p.5

1) Séminaire/Seminar: Suning Wang

Suning Wang

(Queen’s University)

2) Séminaire/Seminar: Benoît Lessard

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For more details visit us at

www.csacs.mcgill.ca

Visit: McGill (Feb. 7)/INRS (Feb. 8)/Sherbrooke (Feb.9)

Titre: Amélioration de la performance des dispositifs électroniques orga-

niques par le biais de l'ingénierie des interfaces : de la polymérisation ini-

tiée en surface hors des électrodes à la réticulation des additifs de phtalo-

cyanine de silicium.

Title: Performance Improvement of organic electronic devices through

Interface Engineering: from surface initiated polymerization off the elec-

trodes to crosslinking silicon phthalocyanine additives.

Résumé/Abstract:

Solution processed organic electronic devices,

such as light emitting diodes (OLEDs) and organic photo-

voltaics (OPVs) have attracted a great deal of attention

over the past decade and while great advances have been

reported there are still some challenges that need to be

overcome. For example, when fabricating more complex

organic electronic devices with multiple thin layers, a

great deal of care is required not to wash away the first

layer with the addition of a second. We explored the use

of nitroxide mediated polymerization (NMP) to facilitate

1) cross linking, 2) grafting-to and 3) grafting-from as

possible techniques for the formation of robust interfacial hole transport layers

between the electrode and the subsequent solution processed layer. In all three

cases these films proved to be robust and resistant to solvent washes while in

comparison simple spin-coated films easily dissolved and wash away. These more

robust films were also found to be electrochemically stable even after several

washes, further justifying their use in the development of multi-layer organic

electronic devices. These studies illustrate three robust routes for the fabrication

of multilayered solution processed organic electronic devices.

Silicon phthalocyanine (SiPc) have two axial bonds originating from the Si atom

which can serve as functionalization sites without affecting the inherent optoelec-

tronic properties of the SiPc macrocycle itself. We have used these handles to en-

gineer an enhanced solid state arrangement of the resulting SiPcs and incorporate

them into planar heterojunction OPVs as either the donor or the acceptor mole-

cules. The devices experienced as much as a 400% increase in efficiency when us-

ing these engineered SiPcs compared to the initial dichloro-SiPc. Additionally,

these handles have also been used to synthesize solution processable ternary ad-

ditives for P3HT:PC61BM bulk heterojunction OPVs with increased photo gener-

ation at the interface which translates to a 20% increase in overall efficiency. Re-

cently we have reported the use of a multifunctional SiPc ternary additive that not

only increase the efficiency of the OPV but also increases the stability by migrat-

ing to the interface and crosslinking the P3HT and PC61BM domains. These stud-

ies are showing potential for SiPcs in OPVs and the axial functionalization to en-

hanced device performance.

Benoît Lessard

(University of Ottawa)

Page 3 CSACS Bulletin du CRMAA

3) Programme de stages internationaux International FRQNT Internship

On a le plaisir de vous informer que deux autres bourses pour le

stage international ont fait l’objet d’une recommandation favorable de finan-

cement par le comité sélection du CRMAA pour les bourses. Pour ceux qui

s'intéressent à la bourse interuniversitaire, s'il vous plaît visitez le site web

du CRMAA.

We have the pleasure to inform you that two additional scholarships

for the international internship (2016-2017) were awarded by the CSACS

scholarship selection committee. For those interested in the inter-university

scholarship please visit our CSACS website.

Au cours de ce stage à l'AMOLF (Amsterdam, Pays-Bas), Alicia étudiera des

voies permettant de contrôler la maniabilité des micro-hélices de silice-

carbonate auto-assemblées et examinera si ces microstructures chirales peu-

vent être utilisées pour générer de la lumière de chiralité simple.

During this internship at AMOLF (Amsterdam, The Netherlands), Alicia

will study routes to control the handedness of self-assembled silica-

carbonate micro helices and investigate whether these chiral microstruc-

tures can be used to generate light of single handedness.

L'oxyde de graphène (GO) est un matériau bidimensionnel qui peut s'auto-

assembler en structures tridimensionnelles telles que des gels ou des mem-

branes. À l'Université de Turin, Richard utilisera leur assemblage FTIR

unique pour étudier, in situ, comment la modification de la chimie du GO, et

donc de l'auto-assemblage de la membrane, affecte le processus d'intercala-

tion.

Graphene oxide (GO) is a two-dimensional material that can self-assemble

into three-dimensional structures such as gels or membranes. In the Univer-

sity of Torino, Richard will used their unique FTIR assembly to investigate,

in-situ, how modifying the GO chemistry and thus the membrane self-

assembly affects the intercalation process.

FÉLICITATIONS! CONGRATULATIONS!

Pour voir la liste complète de nos récipiendaires d’un stage international du

FRQNT, cliquer ici.

To see the complete list of our past prize winners of a FRQNT international

internship, click here.

Alicia McTaggart

(Cuccia)

Durée: 6 mois

Montant: max. 15000$

Où: FOM Institute

AMOLF en Amster-

dam, Pays-Bas.

Accueillie par: Wim

Noorduin

Richard Church

(Cerruti)

Duration: 3 months

Amount: max. 7 500$

Where: University of

Torino, Italy.

Hosted by: Giuliana

Magnacca

Page 4 CSACS Bulletin du CRMAA

4) Programme d'échanges hors Québec de professeurs

FRQNT scientist-in-residence program

C'est avec grand plaisir que nous recevons le Professeur Mark Gal-

lagher comme professeur invité dans le cadre du programme « d'échanges

hors Québec des professeurs ». Le professeur Gallagher sera accueilli par le

laboratoire de Dima Perepichka de mars à août 2017. Ils combineront

leur expertise pour étudier la croissance et la caractérisation des couches or-

ganiques conjuguées sur les surfaces des semi-conducteurs.

It gives us great pleasure to invite Professor Mark Gallagher as a

visiting professor under the program “d’échanges hors Québec de pro-

fesseurs”. Prof. Gallagher will be host by the laboratory of Dima Perepich-

ka from March until August 2017. They will combine their expertise to study

growth and characterization of conjugated organic layers on semiconductor

surfaces.

L'autre demande réussie est adressée au professeur Federico Rosei

de l'INRS. Il se rendra en Californie, plus précisément au California Nano-

Systems Institute, pour travailler avec le professeur Paul Weiss sur la syn-

thèse et la caractérisation des polymères conjugués 2D (analogues orga-

niques du graphène). Le montant maximal de 15 000 $ sera utilisé pour cou-

vrir ses frais de subsistance de 6 mois.

The other successful application goes to Professor Federico Rosei

from INRS. He will be traveling to California more specifically to California

NanoSystems Institute to work with Prof. Paul Weiss on synthesis and

characterization of 2D conjugated polymers (organic analogues of gra-

phene). The maximum value of $15,000 will be use to cover his 6 months

living expenses.

Mark Gallagher

Durée: 6 mois

Montant: max. 15000$

Institution: Lakehead

University, Thunder

Bay, ON

Accueilli par: Dima

Perepichka

Federico Rosei

Duration: 6 months

Amount: max. 15 000$

Where: California

NanoSystems Insti-

tute, Los Angeles, CA

Hosted by: Paul Weiss

Cardenas et al.,

Chem. Sci. 4, 3263

Page 5 CSACS Bulletin du CRMAA

5) Publications

Jean-François Nadon, Kristina

Rochon, Sébastien Grastilleur,

Guillaume Langlois, Thi

Thanh Hà Dao, Véronique

Blais, Brigitte Guérin, Louis

Gendron and Yves Dory.

Synthesis of Gly-ψ[(Z)

CF═CH]-Phe, a Fluoroalkene

Dipeptide Isostere, and Its Incorporation into a Leu-enkephalin Pep-

tidomimetic, ACS Chem. Neurosci.

Jean-Francois Masson. Surface Plasmon Resonance Clinical Biosensors for

Medical Diagnostics, ACS Sens.

M. Tavafoghi, N. Bro-

dusch, R. Gauvin, M.

Cerruti. Hydroxyap-

atite formation on gra-

phene oxide modified

with amino acids: ar-

ginine versus glutamic

acid, J. R. Soc. Inter-

face.

Meng Zhang, Colin Fives,

Karen Waldron and Julian

Zhu. Self-Assembly of a Bile

Acid Dimer in Aqueous Solu-

tions: From Nanofibers to

Nematic Hydrogels, Lang-

muir.

Audrey Laventure,

Jérémie Bourotte,

Jaana Vapaavuori,

Lucas Karperien,

Ribal Georges Sabat

Olivier Lebel and

Christian Pellerin.

Photoactive/Passive

Molecular Glass

Blends: An Efficient

Strategy to Optimize

Azomaterials for

Surface Relief Grat-

ing Inscription, ACS

Appl. Mater. Inter-

faces.

Page 6 CSACS Bulletin du CRMAA

5) Publications con’t

Eva Hemmer, Antonio

Benayas, François Léga-

ré and Fiorenzo Vetro-

ne. Exploiting the bio-

logical windows: cur-

rent perspectives on flu-

orescent bioprobes

emitting above 1000

nm, Nanoscale Horiz.

Philippe Pouliot,

Louis Gagnon, Tina

Lam, Pramod Avti,

Chris Bowen, Michèle

Desjardins, Ashok

Kakkar, E. Thorin,

Sava Sakadzic, David

Boas and Frédéric

Lesage. Magnetic res-

onance fingerprinting based on realistic vasculature in mice, NeuroImage.

A. Syme, H. Lin, J. Rubio-Sanchez and Dima Perepichka. TH-CD-201-12:

Preliminary Evaluation of Organic Field Effect Transistors as Radiation De-

tectors, Medical Physics.

Sébastien Maillette, Caroline Peyrot, Tapas Purkait, Muhammad Iqbal, Jon-

athan Veinot and Kevin Wilkinson. Heteroagglomeration of nanosilver

with colloidal SiO2 and clay, Environ. Chem.

Adamo Riccar-

do Petosa,

Faraz Rajput,

Olivia Selvam,

Carolin Öhl and

Nathalie

Tufenkji. As-

sessing the

transport potential of polymeric nanocapsules developed for crop protec-

tion, Water Research.

McGill University 801 Sherbooke St. West Montreal, Quebec, Canada H3A 0B8

Phone: 514-983-6288 Fax: 514-398-3797 E-mail: csacs.chemistry@mcgill.ca http://www.csacs.mcgill.ca

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