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Issue 19, 2012
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Halogen bonds in 2D supramolecular self-assembly of organic semiconductors†

Rico Gutzler,*ab   Chaoying Fu,ba   Afshin Dadvand,ba   Yun Hua,ab   Jennifer M. MacLeod,a   Federico Rosei*a  and  Dmitrii F. Perepichka*b  
Author affiliations

* Corresponding authors

a Institut National de la Recherche Scientifique and Centre for Self-Assembled Chemical Structures, Université du Québec, 1650 boulevard Lionel-Boulet, Varennes, QC J3X 1S2, Canada
E-mail: gutzler@emt.inrs.ca, rosei@emt.inrs.ca

b Department of Chemistry and Centre for Self-Assembled Chemical Structures, McGill University, 801 Sherbrooke Str. West, Montreal, QC H3A 2K6, Canada
E-mail: dmitrii.perepichka@mcgill.ca

Abstract

Weak interactions between bromine, sulphur, and hydrogen are shown to stabilize 2D supramolecular monolayers at the liquid–solid interface. Three different thiophene-based semiconducting organic molecules assemble into close-packed ultrathin ordered layers. A combination of scanning tunneling microscopy (STM) and density functional theory (DFT) elucidates the interactions within the monolayer. Electrostatic interactions are identified as the driving force for intermolecular Br⋯Br and Br⋯H bonding. We find that the S⋯S interactions of the 2D supramolecular layers correlate with the hole mobilities of thin film transistors of the same materials.

Graphical abstract: Halogen bonds in 2D supramolecular self-assembly of organic semiconductors

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Article information

https://doi.org/10.1039/C2NR31648J
Submitted
27 Jun 2012
Accepted
20 Jul 2012
First published
16 Aug 2012
Nanoscale, 2012,4, 5965-5971
Article type
Paper
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Halogen bonds in 2D supramolecular self-assembly of organic semiconductors

R. Gutzler, C. Fu, A. Dadvand, Y. Hua, J. M. MacLeod, F. Rosei and D. F. Perepichka, Nanoscale, 2012, 4, 5965
DOI: 10.1039/C2NR31648J

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