Controlling conformations of conjugated polymers and small molecules: The role of nonbonding interactions

Nicholas E. Jackson, Brett M. Savoie, Kevin L. Kohlstedt, Monica Olvera De La Cruz, George C. Schatz, Lin X. Chen, Mark A. Ratner

Research output: Contribution to journalArticlepeer-review

256 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)10475-10483
Number of pages9
JournalJournal of the American Chemical Society
Volume135
Issue number28
DOIs
Publication statusPublished - Jul 17 2013

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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