Shedding new light on an old molecule: quinophthalone displays uncommon N-to-O excited state intramolecular proton transfer (ESIPT) between photobases

Abstract Excited state dynamics of common yellow dye quinophthalone (QPH) was probed by femtosecond transient absorption spectroscopy. Multi-exponential decay of the excited state and significant change of rate constants upon deuterium substitution indicate that uncommon nitrogen-to-oxygen excited s...

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Autores principales:	Gi Rim Han, Doyk Hwang, Seunghoon Lee, Jong Woo Lee, Eunhak Lim, Jiyoung Heo, Seong Keun Kim
Formato:	article
Lenguaje:	EN
Publicado:	Nature Portfolio 2017
Materias:	Medicine R Science Q
Acceso en línea:	https://doaj.org/article/4d39df4587d3425eab79a81e8c221e25
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spelling	oai:doaj.org-article:4d39df4587d3425eab79a81e8c221e252021-12-02T15:05:35ZShedding new light on an old molecule: quinophthalone displays uncommon N-to-O excited state intramolecular proton transfer (ESIPT) between photobases10.1038/s41598-017-04114-92045-2322https://doaj.org/article/4d39df4587d3425eab79a81e8c221e252017-06-01T00:00:00Zhttps://doi.org/10.1038/s41598-017-04114-9https://doaj.org/toc/2045-2322Abstract Excited state dynamics of common yellow dye quinophthalone (QPH) was probed by femtosecond transient absorption spectroscopy. Multi-exponential decay of the excited state and significant change of rate constants upon deuterium substitution indicate that uncommon nitrogen-to-oxygen excited state intramolecular proton transfer (ESIPT) occurs. By performing density functional theory (DFT) and time-dependent density functional theory (TDDFT) calculations, we found that adiabatic surface crossing between the S1 and S2 states takes place in the photoreaction. Unlike most cases of ESIPT, QPH does not exhibit tautomer emission, possibly due to internal conversion or back-proton transfer. The ESIPT of QPH presents a highly interesting case also because the moieties participating in ESIPT, quinoline and aromatic carbonyl, are both traditionally considered as photobases.Gi Rim HanDoyk HwangSeunghoon LeeJong Woo LeeEunhak LimJiyoung HeoSeong Keun KimNature PortfolioarticleMedicineRScienceQENScientific Reports, Vol 7, Iss 1, Pp 1-8 (2017)
institution	DOAJ
collection	DOAJ
language	EN
topic	Medicine R Science Q
spellingShingle	Medicine R Science Q Gi Rim Han Doyk Hwang Seunghoon Lee Jong Woo Lee Eunhak Lim Jiyoung Heo Seong Keun Kim Shedding new light on an old molecule: quinophthalone displays uncommon N-to-O excited state intramolecular proton transfer (ESIPT) between photobases
description	Abstract Excited state dynamics of common yellow dye quinophthalone (QPH) was probed by femtosecond transient absorption spectroscopy. Multi-exponential decay of the excited state and significant change of rate constants upon deuterium substitution indicate that uncommon nitrogen-to-oxygen excited state intramolecular proton transfer (ESIPT) occurs. By performing density functional theory (DFT) and time-dependent density functional theory (TDDFT) calculations, we found that adiabatic surface crossing between the S1 and S2 states takes place in the photoreaction. Unlike most cases of ESIPT, QPH does not exhibit tautomer emission, possibly due to internal conversion or back-proton transfer. The ESIPT of QPH presents a highly interesting case also because the moieties participating in ESIPT, quinoline and aromatic carbonyl, are both traditionally considered as photobases.
format	article
author	Gi Rim Han Doyk Hwang Seunghoon Lee Jong Woo Lee Eunhak Lim Jiyoung Heo Seong Keun Kim
author_facet	Gi Rim Han Doyk Hwang Seunghoon Lee Jong Woo Lee Eunhak Lim Jiyoung Heo Seong Keun Kim
author_sort	Gi Rim Han
title	Shedding new light on an old molecule: quinophthalone displays uncommon N-to-O excited state intramolecular proton transfer (ESIPT) between photobases
title_short	Shedding new light on an old molecule: quinophthalone displays uncommon N-to-O excited state intramolecular proton transfer (ESIPT) between photobases
title_full	Shedding new light on an old molecule: quinophthalone displays uncommon N-to-O excited state intramolecular proton transfer (ESIPT) between photobases
title_fullStr	Shedding new light on an old molecule: quinophthalone displays uncommon N-to-O excited state intramolecular proton transfer (ESIPT) between photobases
title_full_unstemmed	Shedding new light on an old molecule: quinophthalone displays uncommon N-to-O excited state intramolecular proton transfer (ESIPT) between photobases
title_sort	shedding new light on an old molecule: quinophthalone displays uncommon n-to-o excited state intramolecular proton transfer (esipt) between photobases
publisher	Nature Portfolio
publishDate	2017
url	https://doaj.org/article/4d39df4587d3425eab79a81e8c221e25
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Shedding new light on an old molecule: quinophthalone displays uncommon N-to-O excited state intramolecular proton transfer (ESIPT) between photobases

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