Theoretical investigation of fluorescence changes caused bymethanol bridge based on ESIPT reaction

doi:10.1088/1674-1056/abf131

中国物理B ›› 2021, Vol. 30 ›› Issue (11): 118202-118202.doi: 10.1088/1674-1056/abf131

Theoretical investigation of fluorescence changes caused bymethanol bridge based on ESIPT reaction

Xinglei Zhang(张星蕾), Lixia Zhu(朱丽霞), Zhengran Wang(王正然), Bifa Cao(曹必发), Qiao Zhou(周悄), You Li(李尤), Bo Li(栗博), Hang Yin(尹航), and Ying Shi(石英)^†

Institute of Atomic and Molecular Physics, Jilin University, Changchun 130012, China

收稿日期:2021-02-04 修回日期:2021-03-10 接受日期:2021-03-24 出版日期:2021-10-13 发布日期:2021-10-27
通讯作者: Ying Shi E-mail:shi_ying@jlu.edu.cn
基金资助:
Project supported by the National Basic Research Program of China (Grant No. 2019YFA0307701), the National Natural Science Foundation of China (Grant No. 11874180), the Young and Middle-aged Scientific and Technological Innovation Leaders and Team Projects in Jilin Province (Grant No. 20200301020RQ).

Theoretical investigation of fluorescence changes caused bymethanol bridge based on ESIPT reaction

Xinglei Zhang(张星蕾), Lixia Zhu(朱丽霞), Zhengran Wang(王正然), Bifa Cao(曹必发), Qiao Zhou(周悄), You Li(李尤), Bo Li(栗博), Hang Yin(尹航), and Ying Shi(石英)^†

Institute of Atomic and Molecular Physics, Jilin University, Changchun 130012, China

Received:2021-02-04 Revised:2021-03-10 Accepted:2021-03-24 Online:2021-10-13 Published:2021-10-27
Contact: Ying Shi E-mail:shi_ying@jlu.edu.cn
Supported by:
Project supported by the National Basic Research Program of China (Grant No. 2019YFA0307701), the National Natural Science Foundation of China (Grant No. 11874180), the Young and Middle-aged Scientific and Technological Innovation Leaders and Team Projects in Jilin Province (Grant No. 20200301020RQ).

摘要/Abstract

摘要： The different fluorescence behavior caused by the excited state proton transfer in 3-hydroxy-4-pyridylisoquinoline (2a) compound has been theoretically investigated. Our calculation results illustrate that the 2a monomer in tetrahydrofuran solvent would not occur proton transfer spontaneously, while the 2a complex in methanol (MeOH) solvent can undergo an asynchronous excited state intramolecular proton transfer (ESIPT) process. The result was confirmed by analyzing the related structural parameters, infrared vibration spectrum and reduced density gradient isosurfaces. Moreover, the potential curves revealed that with the bridging of single MeOH molecular the energy barrier of ESIPT was modulated effectively. It was distinctly reduced to 4.80 kcal/mol in 2a-MeOH complex from 25.01 kcal/mol in 2a monomer. Accordingly, the ESIPT process induced a fluorochromic phenomenon with the assistant of proton-bridge. The elucidation of the mechanism of solvent discoloration will contribute to the design and synthesis of fluorogenic dyes as environment-sensitive probes.

关键词: DFT/TDDFT, fluorochromic, excited state intramolecular proton transfer, methanol bridge

Abstract: The different fluorescence behavior caused by the excited state proton transfer in 3-hydroxy-4-pyridylisoquinoline (2a) compound has been theoretically investigated. Our calculation results illustrate that the 2a monomer in tetrahydrofuran solvent would not occur proton transfer spontaneously, while the 2a complex in methanol (MeOH) solvent can undergo an asynchronous excited state intramolecular proton transfer (ESIPT) process. The result was confirmed by analyzing the related structural parameters, infrared vibration spectrum and reduced density gradient isosurfaces. Moreover, the potential curves revealed that with the bridging of single MeOH molecular the energy barrier of ESIPT was modulated effectively. It was distinctly reduced to 4.80 kcal/mol in 2a-MeOH complex from 25.01 kcal/mol in 2a monomer. Accordingly, the ESIPT process induced a fluorochromic phenomenon with the assistant of proton-bridge. The elucidation of the mechanism of solvent discoloration will contribute to the design and synthesis of fluorogenic dyes as environment-sensitive probes.

Key words: DFT/TDDFT, fluorochromic, excited state intramolecular proton transfer, methanol bridge

中图分类号: (Charge (electron, proton) transfer in biological systems)

82.39.Jn

31.15.ee (Time-dependent density functional theory) 87.15.ht (Ultrafast dynamics; charge transfer)

Xinglei Zhang(张星蕾), Lixia Zhu(朱丽霞), Zhengran Wang(王正然), Bifa Cao(曹必发), Qiao Zhou(周悄), You Li(李尤), Bo Li(栗博), Hang Yin(尹航), and Ying Shi(石英). Theoretical investigation of fluorescence changes caused bymethanol bridge based on ESIPT reaction[J]. 中国物理B, 2021, 30(11): 118202-118202.

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Theoretical investigation of fluorescence changes caused bymethanol bridge based on ESIPT reaction

Theoretical investigation of fluorescence changes caused bymethanol bridge based on ESIPT reaction

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