Sensing Mechanism of Excited-State Intermolecular Hydrogen Bond for Phthalimide: Indispensable Role of Dimethyl Sulfoxide
Dongdong Wang
Key Laboratory of Separation Science for Analytical Chemistry, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian, Liaoning, 116023 China
‡ These authors contributed equally to this work.
Search for more papers by this authorTianxin Bai
Institute of Molecular Sciences and Engineering, Shandong University, Qingdao, Shandong, 266237 China
‡ These authors contributed equally to this work.
Search for more papers by this authorXue Wang
Key Laboratory of Separation Science for Analytical Chemistry, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian, Liaoning, 116023 China
Search for more papers by this authorYuting Xiong
Key Laboratory of Separation Science for Analytical Chemistry, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian, Liaoning, 116023 China
Search for more papers by this authorYahui Zhang
Key Laboratory of Separation Science for Analytical Chemistry, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian, Liaoning, 116023 China
Search for more papers by this authorZhenqiang Shi
Key Laboratory of Separation Science for Analytical Chemistry, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian, Liaoning, 116023 China
Search for more papers by this authorFusheng Zhang
Key Laboratory of Separation Science for Analytical Chemistry, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian, Liaoning, 116023 China
Search for more papers by this authorWenqi Lu
Key Laboratory of Separation Science for Analytical Chemistry, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian, Liaoning, 116023 China
Search for more papers by this authorCorresponding Author
Guangyan Qing
Key Laboratory of Separation Science for Analytical Chemistry, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian, Liaoning, 116023 China
College of Chemistry and Chemical Engineering, Wuhan Textile University, 1 Sunshine Road, Wuhan, Hubei, 430200 China
E-mail: [email protected]Search for more papers by this authorDongdong Wang
Key Laboratory of Separation Science for Analytical Chemistry, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian, Liaoning, 116023 China
‡ These authors contributed equally to this work.
Search for more papers by this authorTianxin Bai
Institute of Molecular Sciences and Engineering, Shandong University, Qingdao, Shandong, 266237 China
‡ These authors contributed equally to this work.
Search for more papers by this authorXue Wang
Key Laboratory of Separation Science for Analytical Chemistry, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian, Liaoning, 116023 China
Search for more papers by this authorYuting Xiong
Key Laboratory of Separation Science for Analytical Chemistry, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian, Liaoning, 116023 China
Search for more papers by this authorYahui Zhang
Key Laboratory of Separation Science for Analytical Chemistry, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian, Liaoning, 116023 China
Search for more papers by this authorZhenqiang Shi
Key Laboratory of Separation Science for Analytical Chemistry, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian, Liaoning, 116023 China
Search for more papers by this authorFusheng Zhang
Key Laboratory of Separation Science for Analytical Chemistry, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian, Liaoning, 116023 China
Search for more papers by this authorWenqi Lu
Key Laboratory of Separation Science for Analytical Chemistry, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian, Liaoning, 116023 China
Search for more papers by this authorCorresponding Author
Guangyan Qing
Key Laboratory of Separation Science for Analytical Chemistry, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian, Liaoning, 116023 China
College of Chemistry and Chemical Engineering, Wuhan Textile University, 1 Sunshine Road, Wuhan, Hubei, 430200 China
E-mail: [email protected]Search for more papers by this authorMain observation and conclusion
Excited-state hydrogen bond strongly affects the intramolecular charge conversion process, which is very suitable for the design and development of high-performance fluorescent probes. However, as one of the most common solvents or additives used in sensing, the role of dimethyl sulfoxide (DMSO) in the system of the excited-state hydrogen bond is seldom explored. As the goal of this research, we investigated the sensing mechanism of a CORM3-green fluorescent probe system for carbon monoxide releasing molecule (CORM-3) detection and tracking in vivo, through quantum chemistry calculations based on density-functional-theory (DFT)/ time-dependent density-functional-theory (TDDFT) methods. Based on the analysis of the solvent effect of DMSO by the reduced density gradient function and IR spectroscopy, we provided a new strategy to explain the fluorescence mechanism. Subsequently, we verified the result through the potential energy curve of Phthalimide (PTI, the reduced product of CORM3-green). The excited-state hydrogen bond between PTI and DMSO promotes radiation transition and leads to obvious difference in the photophysical properties of PTI and PTI-DMSO.
Supporting Information
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Appendix S1: Supporting Information |
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