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Janus-Type ESIPT Chromophores with Distinctive Intramolecular Hydrogen-bonding Selectivity |
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| Authors: | Dr. Yahui Chen Dr. Sheng Lu Syed Ali Abbas Abedi Minseok Jeong Dr. Haidong Li Prof. Myung Hwa Kim Prof. Sungnam Park Prof. Xiaogang Liu Prof. Juyoung Yoon Prof. Xiaoqiang Chen |
| Affiliation: | 1. State Key Laboratory of Materials-Oriented Chemical Engineering, College of Chemical Engineering, Jiangsu National Synergetic Innovation Center for Advanced Materials (SICAM), Nanjing Tech University, 211816 Nanjing, China Department of Chemistry and Nanoscience, Ewha Womans University, 03760 Seoul, Korea New and Renewable Energy Research Center, Ewha Womans University, 03760 Seoul, Korea These authors contributed equally to this work.;2. State Key Laboratory of Materials-Oriented Chemical Engineering, College of Chemical Engineering, Jiangsu National Synergetic Innovation Center for Advanced Materials (SICAM), Nanjing Tech University, 211816 Nanjing, China These authors contributed equally to this work.;3. Fluorescence Research Group, Singapore University of Technology and Design, 8 Somapah Road, 487372 Singapore, Singapore These authors contributed equally to this work.;4. Department of Chemistry and Research Institute for Natural Science, Korea University, 02841 Seoul, Korea These authors contributed equally to this work.;5. School of Bioengineering, Dalian University of Technology, 2 Linggong Road, Hi-tech Zone, 116024 Dalian, China;6. Department of Chemistry and Nanoscience, Ewha Womans University, 03760 Seoul, Korea New and Renewable Energy Research Center, Ewha Womans University, 03760 Seoul, Korea;7. Department of Chemistry and Research Institute for Natural Science, Korea University, 02841 Seoul, Korea;8. Fluorescence Research Group, Singapore University of Technology and Design, 8 Somapah Road, 487372 Singapore, Singapore;9. Department of Chemistry and Nanoscience, Ewha Womans University, 03760 Seoul, Korea;10. State Key Laboratory of Materials-Oriented Chemical Engineering, College of Chemical Engineering, Jiangsu National Synergetic Innovation Center for Advanced Materials (SICAM), Nanjing Tech University, 211816 Nanjing, China |
| 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 |