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Issue 4, 2015
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Supramolecular hierarchy among halogen and hydrogen bond donors in light-induced surface patterning

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Abstract

Halogen bonding, a noncovalent interaction possessing several unique features compared to the more familiar hydrogen bonding, is emerging as a powerful tool in functional materials design. Herein, we unambiguously show that one of these characteristic features, namely high directionality, renders halogen bonding the interaction of choice when developing azobenzene-containing supramolecular polymers for light-induced surface patterning. The study is conducted by using an extensive library of azobenzene molecules that differ only in terms of the bond-donor unit. We introduce a new tetrafluorophenol-containing azobenzene photoswitch capable of forming strong hydrogen bonds, and show that an iodoethynyl-containing azobenzene comes out on top of the supramolecular hierarchy to provide unprecedented photoinduced surface patterning efficiency. Specifically, the iodoethynyl motif seems highly promising in future development of polymeric optical and photoactive materials driven by halogen bonding.

Graphical abstract: Supramolecular hierarchy among halogen and hydrogen bond donors in light-induced surface patterning

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Supplementary files

Article information


Submitted
14 Oct 2014
Accepted
21 Nov 2014
First published
25 Nov 2014

This article is Open Access

J. Mater. Chem. C, 2015,3, 759-768
Article type
Paper
Author version available

Supramolecular hierarchy among halogen and hydrogen bond donors in light-induced surface patterning

M. Saccone, V. Dichiarante, A. Forni, A. Goulet-Hanssens, G. Cavallo, J. Vapaavuori, G. Terraneo, C. J. Barrett, G. Resnati, P. Metrangolo and A. Priimagi, J. Mater. Chem. C, 2015, 3, 759
DOI: 10.1039/C4TC02315C

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