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Janus-Type ESIPT Chromophores with Distinctive Intramolecular Hydrogen-bonding Selectivity
- Title
- Janus-Type ESIPT Chromophores with Distinctive Intramolecular Hydrogen-bonding Selectivity
- Authors
- Chen, Yahui; Lu, Sheng; Abedi, Syed Ali Abbas; Jeong, Minseok; Li, Haidong; Kim, Myung Hwa; Park, Sungnam; Liu, Xiaogang; Yoon, Juyoung; Chen, Xiaoqiang
- Ewha Authors
- 윤주영; 김명화
- SCOPUS Author ID
- 윤주영; 김명화
- Issue Date
- 2023
- Journal Title
- ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
- ISSN
- 1433-7851
1521-3773
- Citation
- ANGEWANDTE CHEMIE-INTERNATIONAL EDITION vol. 62, no. 40
- Keywords
- Competitive Hydrogen Bond Acceptors; Excited-State Intramolecular Proton Transfer; Janus-Type; Quantum Chemical Calculations
- Publisher
- WILEY-V C H VERLAG GMBH
- Indexed
- SCIE; SCOPUS
- Document Type
- Article
- Abstract
- 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.
- DOI
- 10.1002/anie.202311543
- Appears in Collections:
- 자연과학대학 > 화학·나노과학전공 > Journal papers
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