Elaborating and modulating the excited state intramolecular proton transfer behavior for 2-benzothiazole-2-yl-5-hex-1-yn
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Elaborating and modulating the excited state intramolecular proton transfer behavior for 2‑benzothiazole‑2‑yl‑5‑hex‑1‑ynyl‑phenol Xiang Li1 · Yuanyuan Guo2 · Dapeng Yang3 Received: 2 August 2020 / Accepted: 11 November 2020 © Springer-Verlag GmbH Germany, part of Springer Nature 2020
Abstract Excited state intramolecular proton transfer (ESIPT) of organic molecules has been drawing continuously considerable interests. This reaction is not only one of the most basic processes in life, but also exists in wide of application fields. In this work, we theoretically make a thorough inquiry about molecular excited state trends and ESIPT procedures for the novel highly miscible 2-benzothiazole-2-yl-5-hex-1-ynyl-phenol (BYHYP) molecule. Based on DFT and TDDFT means, we firstly examine and certify hydrogen bond O–H···N role in BYHYP. Probing into molecular structure, infrared (IR) vibrational behaviors and computational hydrogen bonding energies, we validate O–H···N of BYHYP is enhanced in S1-state via photoinduced excitation. Accessorial negative electronic densities over N atom facilitate attracting hydrogen proton, which caters to the truth of strengthening hydrogen bond in S1. In addition, frontier orbital gap indicates that the solvent polarity plays vital roles in affecting excited state courses for BYHYP system. By means of potential energy curves (PECs) in four kinds of solvents, we propose the ultrafast ESIPT mechanism for BYHYP by explaining previous experimental characteristics. Along the way of ESIPT, we search the transition state (TS) and present the regulation mechanism for BYHYP via solvent effects. Keywords Intramolecular hydrogen bond · Frontier orbital gap · Solvent effects · ESIPT · Charge redistribution
1 Introduction Hydrogen bond (HB) belongs to one kind of the most fundamental weak interactions, which is ubiquitous in our lives. In fact, it plays vital roles in various fields including biological molecules, organic as well as organometallic compounds and so forth [1–5]. Particularly, by virtue of strong direction interaction, HB has become inevitable architectures for constructing elementary building blocks in nature, which is also the significant active site in biological systems. Thus, Electronic supplementary material The online version of this article (https://doi.org/10.1007/s00214-020-02696-8) contains supplementary material, which is available to authorized users. * Xiang Li [email protected] 1
Henan Institute of Economics and Trade, Zhengzhou 450046, People’s Republic of China
2
School of Mechanical Engineering, Liaoning Shihua University, Fushun 113001, People’s Republic of China
3
School of Physics and Electronics, North China University of Water Resources and Electric Power, Zhengzhou 450046, People’s Republic of China
insights into the HB effects and interactions would be important to probe into and explain novel phenomena occurring in solutions, in crystal forms and in living organisms [6–10]. Excited state intramolecular proton transfer (ESIPT) shou
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