Benzocoumarin‐Fused Triskelions Exhibit AIEE Due to Inhibited Molecular Inversion

Author:

Ueda Masafumi1ORCID,Kuramochi Midori1,Shimizu Riho1,Ohba Yuki2,Yamamoto Norifumi2,Mazaki Yasuhiro1

Affiliation:

1. Department of Chemistry Graduate of School of Science Kitasato University 1-15-1 Kitazato, Minami-ku Sagamihara Kanagawa 252-0373 JAPAN

2. Department of Applied Chemistry Faculty of Engineering Chiba Institute of Technology 2-17-1 Tsudanuma Narashino Chiba 275-0016 JAPAN

Abstract

AbstractDeveloping aggregation‐induced emission luminogens (AIEgens) is a unique strategy for alleviating concentration quenching of π‐conjugated organic compounds. This AIE behaviour can be induced not only in organic dyes with rotors but also in invertible π‐conjugated systems. Herein, intramolecular Ullmann coupling was used to synthesize π‐twisted triskelion‐shaped AIEgens (2F, 2G, and 2H), in which benzo[f], [g], and [h] coumarins were fused into the benzene core to form a helical propeller shape. These structural isomers had unique molecular thicknesses and planarities depending on the fusion mode of the benzocoumarin. The racemic crystals, PPP and MMM, had different overlapping molecular configurations because of their twisted molecular frameworks. Compounds 2F, 2G and 2H demonstrated weak fluorescence emission in diluted solutions resulting from molecular motions caused by the isomerization process during molecular inversion. By comparison, aggregates exhibited enhanced emission intensity. These π‐twisted triskelions exhibited the characteristics of AIEgens.

Funder

Kitasato University

Publisher

Wiley

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