@article{16d734c932ac4ddc8af31d7b9c74d059,
title = "Janus-Type ESIPT Chromophores with Distinctive Intramolecular Hydrogen-bonding Selectivity",
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.",
keywords = "Competitive Hydrogen Bond Acceptors, Excited-State Intramolecular Proton Transfer, Janus-Type, Quantum Chemical Calculations",
author = "Yahui Chen and Sheng Lu and {Abbas Abedi}, {Syed Ali} and Minseok Jeong and Haidong Li and {Hwa Kim}, Myung and Sungnam Park and Xiaogang Liu and Juyoung Yoon and Xiaoqiang Chen",
note = "Funding Information: The work was supported financially by the National Natural Science Foundation of China (22278224 and 21978131 for X. C.) and the Natural Science Foundation of Jiangsu Province (BK20200691 for S. L.). This work was also supported by the Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education (NRF‐2018R1A6A1A03025340) and the Korean government (MSIT) (2022R1A2C3005420 for J. Y. and 2019R1A6A1A11044070 for S. P.). X. L. acknowledged support from A*STAR under its Advanced Manufacturing and Engineering Program (A2083c0051) and the Ministry of Education, Singapore (MOE‐ MOET2EP10120‐0007). The authors are grateful for the supercomputing resources of SUTD‐MIT IDC and the National Supercomputing Centre (Singapore). We thanked the measurements of XRD using the single‐crystal X‐ray spectrometer (Bruker APEX‐II CCD) at the National Research Facilities and Equipment Center (NanoBio⋅Energy Materials Center) at Ewha Womans University. Publisher Copyright: {\textcopyright} 2023 Wiley-VCH GmbH.",
year = "2023",
doi = "10.1002/anie.202311543",
language = "English",
journal = "Angewandte Chemie - International Edition",
issn = "1433-7851",
publisher = "John Wiley and Sons Ltd",
}