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

doi:10.1088/1674-1056/abf131

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.

Keywords: DFT/TDDFT fluorochromic excited state intramolecular proton transfer methanol bridge

Received: 04 February 2021
Revised: 10 March 2021
Accepted manuscript online: 24 March 2021

PACS:	82.39.Jn	(Charge (electron, proton) transfer in biological systems)
	31.15.ee	(Time-dependent density functional theory)
	87.15.ht	(Ultrafast dynamics; charge transfer)

Fund: 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).

Corresponding Authors: Ying Shi
E-mail: shi_ying@jlu.edu.cn

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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 2021 Chin. Phys. B 30 118202

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

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