Triple Emission of 5'-(para-R-Phenylene)vinylene-2-(2'-hydroxyphenyl)benzoxazole (PVHBO). Part I: Dual Emission from the Neutral Species

Meisner, Quinton J.; Hurley, Joseph J. M.; Guo, Peijun; Blood, Anna R.; Schaller, Richard D.; Gosztola, David J.; Wiederrecht, Gary P.; Zhu, Lei

doi:10.1021/acs.jpca.1c10165

Title: Triple Emission of 5'-(para-R-Phenylene)vinylene-2-(2'-hydroxyphenyl)benzoxazole (PVHBO). Part I: Dual Emission from the Neutral Species

Journal Article · 10 February 2022 · Journal of Physical Chemistry. A, Molecules, Spectroscopy, Kinetics, Environment, and General Theory

DOI: https://doi.org/10.1021/acs.jpca.1c10165 · OSTI ID:1854088

^[1]; Hurley, Joseph J. M. ^[1];

^[2]; Blood, Anna R. ^[3];

^[4];

^[4]; Wiederrecht, Gary P. ^[4];

^[1]

Florida State Univ., Tallahassee, FL (United States)
Argonne National Lab. (ANL), Lemont, IL (United States); Yale Univ., New Haven, CT (United States)
New College of Florida, Sarasota, FL (United States)
Argonne National Lab. (ANL), Lemont, IL (United States)

The effects of 5'-(para-R-phenylene)vinylene (PV) substituents on the emission properties of 2-(2'-hydroxyphenyl)benzoxazole (HBO) are analyzed using steady-state and time-resolved absorption and emission spectroscopies in addition to quantum chemical calculations. All members in the series of PVHBOs are capable of excited-state intramolecular proton transfer (ESIPT) with a solvent sensitivity that is typical of a HBO derivative to produce a normal (aka enol) emission and an excited-state tautomer (aka keto) emission. These two emission bands of the neutral dyes are discussed in the current paper. The intermolecular proton transfer, i.e., the deprotonation, of a PVHBO results in the third band of the triple emission, which is described in the succeeding paper. The placement of an electron-withdrawing substituent R on the PVHBO scaffold increases the intensity of the keto emission relative to the enol emission in hydrogen-bonding solvents. The R substituents do not significantly alter the wavelengths of the enol and keto emission bands, which are located in the blue and green regions, respectively, of the visible spectrum. The ultrafast time-resolved spectroscopies and quantum chemical calculations offer explanations on how the R group and the solvent affect the enol and keto emission properties (i.e., wavelength, lifetime, fluorescence quantum yield, and relative ratio of their emissions). Here, the key findings include the following: (1) the emission energies of both enol and keto forms are not sensitively dependent on the R substituent and (2) the solvent-engaged enol excited state is quenched more efficiently as the R substituent becomes more electron-withdrawing. A PVHBO acts as a fusion of HBO and stilbenoid that intersect at the hydroxyphenyl moiety. Depending on the solvent and other environmental conditions, PVHBOs may exhibit the ESIPT property of HBO or the substituent-dependent emission of stilbenoid. This paper and the succeeding article provide a photophysical model of PVHBOs to explain the wavelengths and relative abundances of the three emission bands (enol, keto, and anion) that these compounds are able to produce. Judicial selection of the environmental factors may drive the emission of a PVHBO into the spectral regions of blue, green, and, in a couple of cases, orange or red.

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Research Organization:: Argonne National Laboratory (ANL), Argonne, IL (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES). Scientific User Facilities Division; National Science Foundation (NSF)

Grant/Contract Number:: AC02-06CH11357

OSTI ID:: 1854088

Journal Information:: Journal of Physical Chemistry. A, Molecules, Spectroscopy, Kinetics, Environment, and General Theory, Journal Name: Journal of Physical Chemistry. A, Molecules, Spectroscopy, Kinetics, Environment, and General Theory Journal Issue: 7 Vol. 126; ISSN 1089-5639

Publisher:: American Chemical SocietyCopyright Statement

Country of Publication:: United States

Language:: English

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