Emergent Properties of an Organic Semiconductor Driven by its Molecular Chirality

Ying Yang, Beth Rice, Xingyuan Shi, Jochen R. Brandt, Rosenildo Da Costa, Gordon J. Hedley, Detlef-M. Smilgies, Jarvist M. Frost, Ifor D. W. Samuel, Alberto Otero-de-la-Roza, Erin R. Johnson, Kim E. Jelfs, Jenny Nelson, Alasdair J. Campbell, Matthew J. Fuchter

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Abstract

Chiral molecules exist as pairs of non-superimposable mirror images; a fundamental symmetry property vastly underexplored in organic electronic devices. Here, we show that organic field-effect transistors (OFETs) made from the helically chiral molecule 1-aza[6]helicene can display up to an 80-fold difference in hole mobility, together with differences in thin-film photophysics and morphology, solely depending on whether a single handedness or a 1:1 mixture of left and right handed molecules is employed under analogous fabrication conditions. As the molecular properties of either mirror image isomer are identical, these changes must be a result of the different bulk packing induced by chiral composition. Such underlying structures are investigated using crystal structure prediction, a computational methodology rarely applied to molecular materials, and linked to the difference in charge transport. These results pave the way towards the use of chirality as a key tuning parameter in future device applications.
Original languageEnglish
Pages (from-to)8329-8338
JournalACS Nano
Volume11
Issue number8
Early online date11 Jul 2017
DOIs
Publication statusPublished - 11 Jul 2017

Keywords

  • chirality
  • circular polarization
  • helicene
  • organic semiconductor
  • self-assembling
  • structure prediction

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