Dibenzoarsepins: Planarization of 8π-Electron System in the Lowest Singlet Excited State

Ikuo Kawashima, Hiroaki Imoto, Masatoshi Ishida, Hiroyuki Furuta, Shunsuke Yamamoto, Masaya Mitsuishi, Susumu Tanaka, Toshiki Fujii, Kensuke Naka

    Research output: Contribution to journalArticlepeer-review

    15 Citations (Scopus)

    Abstract

    Dibenzo[b,f]arsepins possessing severely distorted cores compared to those of other heteropins were synthesized. These derivatives exhibited dual photoluminescence in the green-to-red region (500–700 nm) and the near-ultraviolet region (<380 nm), which could be attributed to the planarization of the arsepin core in the lowest singlet excited (S1) state. The computational approach for the assessment of the aromatic indices revealed that the dibenzoarsepins studied show aromaticity (8π system) in the S1 states in line with Baird's rule. The lone pair electrons of the arsenic atoms play a crucial role in the aromaticity in the S1 states.

    Original languageEnglish
    Pages (from-to)11686-11690
    Number of pages5
    JournalAngewandte Chemie - International Edition
    Volume58
    Issue number34
    DOIs
    Publication statusPublished - 2019 Aug 19

    Keywords

    • Baird's rule
    • aromaticity
    • arsepins
    • excited-state aromaticity

    ASJC Scopus subject areas

    • Catalysis
    • Chemistry(all)

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