Cisoid-cis intermediate plays a crucial role in decolouration rate in photochromic reaction of 8H-pyranoquinazolines and 3H-naphthopyrans

Sabina Brazevic; Marek Sikorski; Michel Sliwa; Jiro Abe; Michał F. Rode; Gotard Burdzinski

doi:10.1016/j.dyepig.2022.110249

Cisoid-cis intermediate plays a crucial role in decolouration rate in photochromic reaction of 8H-pyranoquinazolines and 3H-naphthopyrans

Sabina Brazevic
, Marek Sikorski
, Michel Sliwa
, Jiro Abe
, Michał F. Rode
, Gotard Burdzinski

Adam Mickiewicz University/Faculty of Biology
Université de Lille
Aoyama Gakuin University
Institute of Physics of the Polish Academy of Sciences

Research output: Contribution to journal › Article › peer-review

8 Citations (Scopus)

Abstract

The photochromic reaction of 8H-pyranoquinazoline shows intriguing aspects in comparison to 3H-naphthopyrans. These come from a stabilized excited singlet state for 8 H-pyranoquinazoline, which has a longer lifetime and is strongly sensitive to the solvent. The polar solvent acetonitrile reduces the quantum yield of coloured isomer formation (transoid-cis species). Colour fading related to the decay of transoid-cis population is faster than that for 3H-naphthopyran family and occurs within few seconds time-window in solution at room temperature. Theoretical calculations show the crucial role in fading process played by the potential energy landscape, with the cisoid-cis intermediate located in a shallow high-energy minimum.

Original language	English
Article number	110249
Journal	Dyes and Pigments
Volume	201
DOIs	https://doi.org/10.1016/j.dyepig.2022.110249
Publication status	Published - 1 May 2022
Externally published	Yes

Keywords

3H-naphthopyrans
8H-pyranoquinazolines
Ab initio calculations
Colour fading mechanism
Photochromism
Time-resolved spectroscopy

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10.1016/j.dyepig.2022.110249

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title = "Cisoid-cis intermediate plays a crucial role in decolouration rate in photochromic reaction of 8H-pyranoquinazolines and 3H-naphthopyrans",

abstract = "The photochromic reaction of 8H-pyranoquinazoline shows intriguing aspects in comparison to 3H-naphthopyrans. These come from a stabilized excited singlet state for 8 H-pyranoquinazoline, which has a longer lifetime and is strongly sensitive to the solvent. The polar solvent acetonitrile reduces the quantum yield of coloured isomer formation (transoid-cis species). Colour fading related to the decay of transoid-cis population is faster than that for 3H-naphthopyran family and occurs within few seconds time-window in solution at room temperature. Theoretical calculations show the crucial role in fading process played by the potential energy landscape, with the cisoid-cis intermediate located in a shallow high-energy minimum.",

keywords = "3H-naphthopyrans, 8H-pyranoquinazolines, Ab initio calculations, Colour fading mechanism, Photochromism, Time-resolved spectroscopy",

author = "Sabina Brazevic and Marek Sikorski and Michel Sliwa and Jiro Abe and Rode, \{Micha{\l} F.\} and Gotard Burdzinski",

note = "Publisher Copyright: {\textcopyright} 2022 Elsevier Ltd",

year = "2022",

month = may,

day = "1",

doi = "10.1016/j.dyepig.2022.110249",

language = "English",

volume = "201",

journal = "Dyes and Pigments",

issn = "0143-7208",

publisher = "Elsevier B.V.",

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TY - JOUR

T1 - Cisoid-cis intermediate plays a crucial role in decolouration rate in photochromic reaction of 8H-pyranoquinazolines and 3H-naphthopyrans

AU - Brazevic, Sabina

AU - Sikorski, Marek

AU - Sliwa, Michel

AU - Abe, Jiro

AU - Rode, Michał F.

AU - Burdzinski, Gotard

PY - 2022/5/1

Y1 - 2022/5/1

N2 - The photochromic reaction of 8H-pyranoquinazoline shows intriguing aspects in comparison to 3H-naphthopyrans. These come from a stabilized excited singlet state for 8 H-pyranoquinazoline, which has a longer lifetime and is strongly sensitive to the solvent. The polar solvent acetonitrile reduces the quantum yield of coloured isomer formation (transoid-cis species). Colour fading related to the decay of transoid-cis population is faster than that for 3H-naphthopyran family and occurs within few seconds time-window in solution at room temperature. Theoretical calculations show the crucial role in fading process played by the potential energy landscape, with the cisoid-cis intermediate located in a shallow high-energy minimum.

AB - The photochromic reaction of 8H-pyranoquinazoline shows intriguing aspects in comparison to 3H-naphthopyrans. These come from a stabilized excited singlet state for 8 H-pyranoquinazoline, which has a longer lifetime and is strongly sensitive to the solvent. The polar solvent acetonitrile reduces the quantum yield of coloured isomer formation (transoid-cis species). Colour fading related to the decay of transoid-cis population is faster than that for 3H-naphthopyran family and occurs within few seconds time-window in solution at room temperature. Theoretical calculations show the crucial role in fading process played by the potential energy landscape, with the cisoid-cis intermediate located in a shallow high-energy minimum.

KW - 3H-naphthopyrans

KW - 8H-pyranoquinazolines

KW - Ab initio calculations

KW - Colour fading mechanism

KW - Photochromism

KW - Time-resolved spectroscopy

U2 - 10.1016/j.dyepig.2022.110249

DO - 10.1016/j.dyepig.2022.110249

M3 - Article

AN - SCOPUS:85126833143

SN - 0143-7208

VL - 201

JO - Dyes and Pigments

JF - Dyes and Pigments

M1 - 110249

ER -

Cisoid-cis intermediate plays a crucial role in decolouration rate in photochromic reaction of 8H-pyranoquinazolines and 3H-naphthopyrans

Abstract

Keywords

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