Exploration and elaboration of photo-induced proton transfer dynamical mechanism for novel 2-[1,3]dithian-2-yl-6-(7aH-indol-2-yl)-phenol sensor

doi:10.1088/1674-1056/ab8208

Abstract In this work, we theoretically probe into the photo-induced hydrogen bonding effects between S0 state and S1 state as well as the excited state intramolecular proton transfer (ESIPT) behavior for a novel 2-[1,3]dithian-2-yl-6-(7 aH-indol-2-yl)-phenol (DIP) probe system. We first study the ground-state hydrogen bonding O-H…N behavior for DIP. Then we analyze the primary geometrical parameters (i.e., bond length, bond angle, and infrared (IR) stretching vibrational mode) involved in hydrogen bond, and confirm that the O-H…N of DIP should be strengthened in the first excited state. It is the significant prerequisite for ESIPT reaction. Combining the frontier molecular orbitals (MOs) with vertical excitation analyses, the intramolecular charge transfer (ICT) phenomenon can be found for the DIP system, which reveals that the charge redistribution facilitates ESIPT behavior. By constructing potential energy curves for DIP along the ESIPT reactional orientation, we obtain quite a small energy barrier (3.33 kcal/mol) and affirmed that the DIP molecule undergoes ultrafast ESIPT process once it is excited to the S1 state and quickly transfers its proton, forming DIP-keto tautomer. That is why no fluorescence of DIP can be observed in experiment, which further reveals the ultrafast ESIPT mechanism proposed in this work.

Keywords: intramolecular charge transfer ESIPT molecular electrostatic potential potential energy curves

Received: 12 January 2020
Revised: 23 February 2020
Accepted manuscript online:

PACS:	31.15.ee	(Time-dependent density functional theory)
	31.15.ae	(Electronic structure and bonding characteristics)
	31.15.es	(Applications of density-functional theory (e.g., to electronic structure and stability; defect formation; dielectric properties, susceptibilities; viscoelastic coefficients; Rydberg transition frequencies))

Fund: Project supported by the National Natural Science Foundation of China (Grant No. 11574083).

Corresponding Authors: Da-Peng Yang
E-mail: dpyang_ncwu@163.com

Cite this article:

Lei Xu(许磊), Tian-Jie Zhang(张天杰), Qiao-Li Zhang(张巧丽), Da-Peng Yang(杨大鹏) Exploration and elaboration of photo-induced proton transfer dynamical mechanism for novel 2-[1,3]dithian-2-yl-6-(7aH-indol-2-yl)-phenol sensor 2020 Chin. Phys. B 29 053102

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Exploration and elaboration of photo-induced proton transfer dynamical mechanism for novel 2-[1,3]dithian-2-yl-6-(7aH-indol-2-yl)-phenol sensor

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