A novel non-fluorescent excited state intramolecular proton transfer phenomenon induced by intramolecular hydrogen bonds: an experimental and theoretical investigation

Scientific Reports
Hang YinDajun Ding

Abstract

Two molecules, 1-hydroxypyrene-2-carbaldehyde (HP) and 1-methoxypyrene-2-carbaldehyde (MP) were explored. We investigated their photophysical properties, using experimental transient absorption and theoretical density functional theory/time-dependent density functional theory (DFT/TDDFT). HP and MP have similar geometric conformations but exhibit entirely different photophysical properties upon excitation into the S1 state. In contrast to traditional excited state intramolecular proton transfer (ESIPT) in molecules that exhibit either single or dual fluorescence, HP has an unusual non-fluorescent property. Specifically, the ultrafast ESIPT process occurs in 158 fs and is followed by an intersystem crossing (ISC) component of 11.38 ps. In contrast to HP, MP undergoes only an 8 ps timescale process, which was attributed to interactions between solute and solvent. We concluded that this difference arises from intramolecular hydrogen bonds (IMHBs), which induce drastic structural alterntion upon excitation.

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Citations

Jul 3, 2017·The Journal of Chemical Physics·Pan MaDajun Ding
Jan 13, 2018·Antioxidants & Redox Signaling·Xiqian JiangJin Wang
Aug 3, 2018·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Bhupendra Kumar DwivediDaya Shankar Pandey
Nov 20, 2018·Physical Chemistry Chemical Physics : PCCP·Wilver A MurielWilliam Rodríguez-Córdoba
Nov 8, 2018·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Grzegorz CzernelAndrzej Niewiadomy
May 1, 2021·Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy·Xiao LuoYongqing Li
May 23, 2021·Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy·Yu ZhaoQingtian Meng
Aug 29, 2019·Journal of Chemical Theory and Computation·Boris MaulénCarlos Cardenas
Nov 10, 2018·The Journal of Physical Chemistry. a·Quinton J MeisnerLei Zhu
Mar 1, 2018·The Journal of Physical Chemistry. a·Quinton J MeisnerLei Zhu
Jan 18, 2019·ACS Sensors·Yuna JungDokyoung Kim
Feb 2, 2019·The Journal of Physical Chemistry Letters·Hui LiDajun Ding

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