To bend or not to bend – are heteroatom interactions within conjugated molecules effective in dictating conformation and planarity?

Gary Conboy; Howard J. Spencer; Enrico Angioni; Alexander L. Kanibolotsky; Neil J. Findlay; Simon J. Coles; Claire Wilson; Mateusz B. Pitak; Chad Risko; Veaceslav Coropceanu; Jean-Luc Brédas; Peter J. Skabara

doi:10.1039/C6MH00051G

To bend or not to bend – are heteroatom interactions within conjugated molecules effective in dictating conformation and planarity?†

Gary Conboy,^a Howard J. Spencer,^b Enrico Angioni,^a Alexander L. Kanibolotsky,^ac Neil J. Findlay,^a Simon J. Coles,

^d Claire Wilson,^d Mateusz B. Pitak,^d Chad Risko,^e Veaceslav Coropceanu,^f Jean-Luc Brédas^g and Peter J. Skabara*^a

Author affiliations

* Corresponding authors

^a WestCHEM, Department of Pure and Applied Chemistry, University of Strathclyde, Glasgow, UK
E-mail: peter.skabara@strath.ac.uk

^b School of Chemistry, University of Manchester, Manchester M13 9PL, UK

^c Institute of Physical-Organic Chemistry and Coal Chemistry, 02160 Kyiv, Ukraine

^d School of Chemistry, University of Southampton, Highfield, Southampton, UK

^e Department of Chemistry and Center for Applied Energy Research, University of Kentucky, Lexington, Kentucky 40506-0055, USA

^f School of Chemistry and Biochemistry and Center for Organic Photonics and Electronics, Georgia Institute of Technology, Atlanta, Georgia, USA

^g Physical Science and Engineering Division, King Abdullah University of Science and Technology, Thuwal 23955-6900, Kingdom of Saudi Arabia

Abstract

We consider the roles of heteroatoms (mainly nitrogen, the halogens and the chalcogens) in dictating the conformation of linear conjugated molecules and polymers through non-covalent intramolecular interactions. Whilst hydrogen bonding is a competitive and sometimes more influential interaction, we provide unambiguous evidence that heteroatoms are able to determine the conformation of such materials with reasonable predictability.

Materials Horizons

To bend or not to bend – are heteroatom interactions within conjugated molecules effective in dictating conformation and planarity?†

Abstract

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To bend or not to bend – are heteroatom interactions within conjugated molecules effective in dictating conformation and planarity?

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