Tris(pentafluorophenyl)borane-pyrrolo[3,2-b]pyrrole Hybrids: Solid-State Structure and Crystallization-Induced Enhanced Emission

Sou Hatanaka, Toshikazu Ono, Yoshio Yano, Daniel T. Gryko, Yoshio Hisaeda

Research output: Contribution to journalArticle

Abstract

The work demonstrates that the quadrupolar nature of acceptor-donor-acceptor pyrrolo[3,2-b]pyrrole systems can be substantially modified via the formation of boron-nitrogen (B−N) bonds between peripheral CN groups and B(C6F5)3. This coordination enables a strong bathochromic shift of emission for both the solid crystalline state as well as in certain solvents. The B−N complex, or co-crystal, was effectively isolated from the reaction between a pyrrolo[3,2-b]pyrrole with two cyanophenyl moieties and tris(pentafluorophenyl)borane (TPFB), which were mixed in non-polar solvents or prepared via liquid-assisted solid-state synthesis in a ball mill. An investigation of the structure-property relationship confirmed that the intermolecular B−N bond influences the bathochromic shift in the absorption and emission spectra and that crystallization-induced emission enhancement was observed owing to the benefits of the molecular packing style and the intermolecular C−H⋅⋅⋅F interactions. The postsynthetic strategy involves hybridization of molecules on a molecular level, which should provide a variety of novel photofunctional materials.

Original languageEnglish
Pages (from-to)138-143
Number of pages6
JournalChemPhotoChem
Volume4
Issue number2
DOIs
Publication statusPublished - Feb 1 2020

All Science Journal Classification (ASJC) codes

  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Analytical Chemistry

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