Janus‐Type ESIPT Chromophores with Distinctive Intramolecular Hydrogen‐bonding Selectivity

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...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2023-10, Vol.62 (40), p.e202311543-n/a
Main Authors: Chen, Yahui, Lu, Sheng, Abbas Abedi, Syed Ali, Jeong, Minseok, Li, Haidong, Hwa Kim, Myung, Park, Sungnam, Liu, Xiaogang, Yoon, Juyoung, Chen, Xiaoqiang
Format: Article
Language:English
Subjects:
Benzothiazole
Chromophores
Competitive Hydrogen Bond Acceptors
Excited-State Intramolecular Proton Transfer
Fluorescence
Hydrazones
Hydrogen
Hydrogen bonds
Hydroxyl groups
Imines
Janus-Type
Quantum Chemical Calculations
Quantum chemistry
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Summary: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. A new family of Janus‐type ESIPT chromophores with distinctive hydrogen bonding selectivity between competitive hydrogen bond acceptors (HBAs) were reported. Single‐crystal structures and theoretical studies unveiled the molecular origins of the biased intramolecular hydrogen bonds (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.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.202311543