Influence of the hydrogen-bond interactions on the excited-state dynamics of a push-pull azobenzene dye: the case of Methyl Orange

Physical Chemistry Chemical Physics : PCCP
Christoph NançozEric Vauthey

Abstract

The excited-state dynamics of the push-pull azobenzene Methyl Orange (MO) were investigated in several solvents and water/glycerol mixtures using a combination of ultrafast time-resolved fluorescence and transient absorption in both the UV-visible and the IR regions, as well as quantum chemical calculations. Optical excitation of MO in its trans form results in the population of the S2ππ* state and is followed by internal conversion to the S1nπ* state in ∼50 fs. The population of this state decays on the sub-picosecond timescale by both internal conversion to the trans ground state and isomerisation to the cis ground state. Finally, the cis form converts thermally to the trans form on a timescale ranging from less than 50 ms to several minutes. Significant differences depending on the hydrogen-bond donor strength of the solvents, quantified by the Kamlet Taft parameter α, were observed: compared to the other solvents, in highly protic solvents (α > 1), (i) the viscosity dependence of the S1state lifetime is less pronounced, (ii) the S1state lifetime is shorter by a factor of ≈1.5 for the same viscosity, (iii) the trans-to-cis photoisomerisation efficiency is smaller, and (iv) the thermal cis-to-trans isomerisation is faster by ...Continue Reading

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Citations

May 24, 2018·Physical Chemistry Chemical Physics : PCCP·Peter S SherinEnrico Benassi
Mar 30, 2019·Chemistry : a European Journal·Jaume Garcia-AmorósDolores Velasco
Mar 21, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Rosita DianaBarbara Panunzi
Feb 21, 2021·The Journal of Chemical Physics·Learnmore ShenjeSusanne Ullrich
Sep 28, 2018·The Journal of Physical Chemistry Letters·Alberto TorresLuis G C Rego

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Methods Mentioned

BETA
FRET

Software Mentioned

MO
FLUPS

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