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Uncovering the effects of different substituents on excited state hydrogen-bonding interaction and fluorescent behavior in BTN system: a TD-DFT insight

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Abstract

The effect of different substituents on the electronic spectra and excited state intramolecular hydrogen-bonding interactions of 2-(2-aminophenyl)benzothiazole (BTN) and its derivatives (BTN-1, BTN-2, BTN-3) were studied by using the density functional theory (DFT) and time-dependent DFT (TD-DFT) methods. The structural parameters, infrared vibrational frequencies, topological parameters, frontier molecular orbitals, absorption and emission spectra as well as potential energy curves in the ground (S0) and excited (S1) states were obtained. BTN and its derivatives are difficult to undergo ESIPT process since the reverse ESIPT barriers are about 6–7 kcal/mol lower than the corresponding forward ESIPT barriers. The experimental fluorescence emission wavelength of BTN is originated from its normal form, and is well reproduced theoretically. As the electron-donating ability of functional group increases from –CH3 to –OCH3, the absorption and fluorescence wavelengths red-shift more. The S0 and S1 energy gap is in the order of BTN > BTN-1 > BTN-2 > BTN-3, which is in good agreement with its red-shift values of absorption and emission peaks.

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  1. Department of Chemistry and Material Science, College of Science, Nanjing Forestry University, Nanjing, 210037, People’s Republic of China

    Zhengyi Zhang & Hua Fang

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  1. Zhengyi Zhang
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Data curation, writing—original draft preparation, visualization and investigation were performed by ZZ. Conceptualization, methodology, software, supervision, validation, writing—reviewing and editing were performed by HF. All authors approved the final manuscript.

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Correspondence to Hua Fang.

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Zhang, Z., Fang, H. Uncovering the effects of different substituents on excited state hydrogen-bonding interaction and fluorescent behavior in BTN system: a TD-DFT insight. Theor Chem Acc 142, 109 (2023). https://doi.org/10.1007/s00214-023-03054-0

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