Controlling Conformations of Conjugated Polymers and Small Molecules: The Role of Nonbonding Interactions

2013/06/25 by Nicholas E. Jackson, Brett M. Savoie, Kevin L. Kohlstedt +5 · 29 citations
Engineering · Materials Science · #Organic Electronics and Photovoltaics #Conducting polymers and applications #Synthesis and properties of polymers

paper · doi:10.1021/ja403667s

Abstract

The chemical variety present in the organic electronics literature has motivated us to investigate potential nonbonding interactions often incorporated into conformational "locking" schemes. We examine a variety of potential interactions, including oxygen-sulfur, nitrogen-sulfur, and fluorine-sulfur, using accurate quantum-chemical wave function methods and noncovalent interaction (NCI) analysis on a selection of high-performing conjugated polymers and small molecules found in the literature. In addition, we evaluate a set of nonbonding interactions occurring between various heterocyclic and pendant atoms taken from a group of representative π-conjugated molecules. Together with our survey and set of interactions, it is determined that while many nonbonding interactions possess weak binding capabilities, nontraditional hydrogen-bonding interactions, oxygen-hydrogen (CH···O) and nitrogen-hydrogen (CH···N), are alone in inducing conformational control and enhanced planarity along a polymer or small molecule backbone at room temperature.

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