"disrupt and induce" intermolecular interactions to rationally design organic semiconductor crystals: From herringbone to rubrene-like pitched π-stacking

Chengyuan Wang, Daisuke Hashizume, Masahiro Nakano, Takuya Ogaki, Hiroyuki Takenaka, Kohsuke Kawabata, Kazuo Takimiya

Research output: Contribution to journalArticlepeer-review

14 Citations (Scopus)

Abstract

The packing structures of organic semiconductors in the solid state play critical roles in determining the performances of their optoelectronic devices, such as organic field-effect transistors (OFETs). It is a formidable challenge to rationally design molecular packing in the solid state owing to the difficulty of controlling intermolecular interactions. Here we report a unique materials design strategy based on the β-methylthionation of acenedithiophenes to generally and selectively control the packing structures of materials to create organic semiconductors rivalling rubrene, a benchmark high-mobility material with a characteristic pitched π-stacking structure in the solid state. Furthermore, the effect of the β-methylthionation on the packing structure was analyzed by Hirshfeld surface analysis together with theoretical calculations based on symmetry-adapted perturbation theory (SAPT). The results clearly demonstrated that the β-methylthionation of acenedithiophenes can universally alter the intermolecular interactions by disrupting the favorable edge-to-face manner in the parent acenedithiophenes and simultaneously inducing face-to-face and end-to-face interactions in the β-methylthionated acenedithiophenes. This "disrupt and induce" strategy to manipulate intermolecular interactions can open a door to rational packing design based on the molecular structure.

Original languageEnglish
Pages (from-to)1573-1580
Number of pages8
JournalChemical Science
Volume11
Issue number6
DOIs
Publication statusPublished - 2020 Feb 14

ASJC Scopus subject areas

  • Chemistry(all)

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