Issue 64, 2016, Issue in Progress

Detailed theoretical investigation on ESIPT process of pigment yellow 101

Abstract

Based on density functional theory (DFT) and time-dependent density functional theory (TDDFT) methods, the detailed excited state intramolecular proton transfer (ESIPT) mechanism of 2,2′-dihydroxy-1,1′-naphthalazine (P.Y. 101) has been investigated theoretically. Unlike previous theoretical investigation of P.Y. 101, our calculated results not only reproduce the absorption and fluorescence spectra reported in the previous experiment, but also were completed with considering solvent effect. It further demonstrates that the TDDFT theory we adopted is very reasonable and effective. The calculations of main bond lengths and bond angles involving in the hydrogen bondings (O1–H2⋯N3 and O4–H5⋯N6) as well as the infrared vibrational spectra and as well as the calculated hydrogen bonding energies demonstrated the intramolecular hydrogen bond was strengthened in the S1 state. In addition, qualitative and quantitative intramolecular charge transfer based on the frontier molecular orbitals provided the possibility of the ESIPT reaction. The potential energy surfaces of ground state and the first excited state have been constructed to illustrate the ESIPT mechanism. Based on our calculations, the equilibrium ESIPT process exists in the S1 state. And after the radiative transition, reversed GSIPT can also occur in the S0 state.

Graphical abstract: Detailed theoretical investigation on ESIPT process of pigment yellow 101

Article information

Article type
Paper
Submitted
29 Apr 2016
Accepted
16 Jun 2016
First published
17 Jun 2016

RSC Adv., 2016,6, 59389-59394

Detailed theoretical investigation on ESIPT process of pigment yellow 101

M. Zhang, Q. Zhou, C. Du, Y. Ding and P. Song, RSC Adv., 2016, 6, 59389 DOI: 10.1039/C6RA11140H

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