Janus-Type ESIPT Chromophores with Distinctive Intramolecular Hydrogen-bonding Selectivity
- 주제(키워드) Competitive Hydrogen Bond Acceptors , Excited-State Intramolecular Proton Transfer , Janus-Type , Quantum Chemical Calculations
- 등재 SCIE, SCOPUS
- 발행기관 John Wiley and Sons Inc
- 발행년도 2023
- 총서유형 Journal
- URI http://www.dcollection.net/handler/ewha/000000211518
- 본문언어 영어
- Published As https://doi.org/10.1002/anie.202311543
- PubMed 37602709
초록/요약
Excited-state intramolecular proton transfer (ESIPT)-based solid luminescent materials with multiple hydrogen bond acceptors (HBAs) remain unexplored. Herein, we introduced a family of Janus-type ESIPT chromophores featuring distinctive hydrogen bond (H-bond) selectivity between competitive HBAs in a single molecule. Our investigations showed that the central hydroxyl group preferentially forms intramolecular H-bonds with imines in imine-modified 2-hydroxyphenyl benzothiazole (HBT) chromophores but tethers the benzothiazole moiety in hydrazone-modified HBT chromophores. Imine-derived HBTs generally exhibit higher fluorescence efficiency, while hydrazone-derived HBTs show a reduced overlap between the absorption and fluorescence bands. Quantum chemical calculations unveiled the molecular origins of the biased intramolecular H-bonds and their impact on the ESIPT process. This Janus-type ESIPT chromophore skeleton provides new opportunities for the design of solid luminescent materials. © 2023 Wiley-VCH GmbH.
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