Modulation of π-stacking modes and photophysical properties of an organic semiconductor through isosteric cocrystallization

Gonzalo Campillo-Alvarado, Michael Bernhardt, Daniel W. Davies, Julio A.N.T. Soares, Toby J. Woods, Ying Diao

Research output: Contribution to journalArticlepeer-review

Abstract

We report on the control of π-stacking modes (herringbone vs slipped-stack) and photophysical properties of 9,10-bis((E)-2-(pyridin-4-yl)vinyl)anthracene (BP4VA), an anthracene-based organic semiconductor (OSC), by isosteric cocrystallization (i.e., the replacement of one functional group in a coformer with another of "similar"electronic structure) with 2,4,6-trihalophenols (3X-ph-OH, where X = Cl, Br, and I). Specifically, BP4VA organizes as slipped-stacks when cocrystallized with 3Cl-ph-OH and 3Br-ph-OH, while cocrystallization with 3I-ph-OH results in a herringbone mode. The photoluminescence and molecular frontier orbital energy levels of BP4VA were effectively modulated by the presence of 3X-ph-OH through cocrystallization. We envisage that the cocrystallization of OSCs with minimal changes in cocrystal formers can provide access to convenient structural and property diversification for advanced single-crystal electronics.

Original languageEnglish (US)
Article number0059770
JournalThe Journal of Chemical Physics
Volume155
Issue number7
DOIs
StatePublished - Aug 21 2021

ASJC Scopus subject areas

  • General Physics and Astronomy
  • Physical and Theoretical Chemistry

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