Crystal Structures of Dimethoxyanthracens: A Clue to a Rational Design of Packing Structures of π-Conjugated Molecules

Kazuo Takimiya, Takuya Ogaki, Chengyuan Wang, Kohsuke Kawabata

Research output: Contribution to journalArticle

Abstract

We carried out a systematic investigation of packing structures of a series of dimethoxyanthracenes, i. e., 1,4- (1), 1,8- (2), 1,5- (3), 2,6- (4), and 2,7-derivatives (5). The packing structures of the dimethoxyanthracenes are classified into two types, a rubrene-like pitched π-stack (1–3) and a typical herringbone packing (4 and 5), which evidently show that the position of methoxy groups is crucial to determine the packing structure of dimethoxyanthracenes. Effects of the substitution position on intermolecular interactions are analyzed by the noncovalent intermolecular interaction (NCI) method, Hirshfeld surface analysis, and symmetry-adapted perturbation theory (SAPT) method, thus clarifying active roles of the methoxy groups in the formation of rubrene-like pitched π-stack. The present results shed light on a molecular design strategy to realize the rubrene-like pitched π-stack in the solid state, which had been regarded as a packing structure limited for rubrene and its closely related derivatives.

Original languageEnglish
Pages (from-to)915-919
Number of pages5
JournalChemistry - An Asian Journal
Volume15
Issue number6
DOIs
Publication statusPublished - 2020 Mar 16

Keywords

  • crystal structures
  • dimethoxyanthracenes
  • intermolecular interactions
  • rubrene-like pitched π-stacking

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry

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