Mechanistic insights into photochromic 3H-naphthopyran showing strong photocoloration
Abstract 3,3-Diphenylbenzo[f]chromene (1) represents an important architectural platform for photochromic systems. Since the practical utility of such chromophores is largely dependent upon the kinetics of coloration and decoloration, elucidating the mechanistic details of these processes is of grea...
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Format: | Article |
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Nature Portfolio
2022-06-01
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Series: | Scientific Reports |
Online Access: | https://doi.org/10.1038/s41598-022-14679-9 |
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author | Błażej Gierczyk Michał F. Rode Gotard Burdzinski |
author_facet | Błażej Gierczyk Michał F. Rode Gotard Burdzinski |
author_sort | Błażej Gierczyk |
collection | DOAJ |
description | Abstract 3,3-Diphenylbenzo[f]chromene (1) represents an important architectural platform for photochromic systems. Since the practical utility of such chromophores is largely dependent upon the kinetics of coloration and decoloration, elucidating the mechanistic details of these processes is of great value. Toward this end, we studied the photochromic reaction of (3-(2-methoxyphenyl)-3-phenyl-3H-benzo[f]chromene (2) by both time-resolved UV–vis and mid-IR spectroscopies. We found that irradiation of 2 at 365 nm generates long-lived colored transoid-cis isomers with lifetimes of 17.1 s and 17.5 min (at 21 °C) and even longer-lived transoid-trans isomers with a lifetime of 16 h. These experimental results were supplemented with ab initio ground-state and excited-state calculations, and the resulting theoretical interpretation may be useful for the design of new photochromic systems with optimized photofunctionality. |
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issn | 2045-2322 |
language | English |
last_indexed | 2024-04-13T17:09:52Z |
publishDate | 2022-06-01 |
publisher | Nature Portfolio |
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series | Scientific Reports |
spelling | doaj.art-5df602b31fd344feb4c1a4b3a71d65ba2022-12-22T02:38:18ZengNature PortfolioScientific Reports2045-23222022-06-011211810.1038/s41598-022-14679-9Mechanistic insights into photochromic 3H-naphthopyran showing strong photocolorationBłażej Gierczyk0Michał F. Rode1Gotard Burdzinski2Faculty of Chemistry, Adam Mickiewicz University in PoznańInstitute of Physics, Polish Academy of SciencesFaculty of Physics, Adam Mickiewicz University in PoznańAbstract 3,3-Diphenylbenzo[f]chromene (1) represents an important architectural platform for photochromic systems. Since the practical utility of such chromophores is largely dependent upon the kinetics of coloration and decoloration, elucidating the mechanistic details of these processes is of great value. Toward this end, we studied the photochromic reaction of (3-(2-methoxyphenyl)-3-phenyl-3H-benzo[f]chromene (2) by both time-resolved UV–vis and mid-IR spectroscopies. We found that irradiation of 2 at 365 nm generates long-lived colored transoid-cis isomers with lifetimes of 17.1 s and 17.5 min (at 21 °C) and even longer-lived transoid-trans isomers with a lifetime of 16 h. These experimental results were supplemented with ab initio ground-state and excited-state calculations, and the resulting theoretical interpretation may be useful for the design of new photochromic systems with optimized photofunctionality.https://doi.org/10.1038/s41598-022-14679-9 |
spellingShingle | Błażej Gierczyk Michał F. Rode Gotard Burdzinski Mechanistic insights into photochromic 3H-naphthopyran showing strong photocoloration Scientific Reports |
title | Mechanistic insights into photochromic 3H-naphthopyran showing strong photocoloration |
title_full | Mechanistic insights into photochromic 3H-naphthopyran showing strong photocoloration |
title_fullStr | Mechanistic insights into photochromic 3H-naphthopyran showing strong photocoloration |
title_full_unstemmed | Mechanistic insights into photochromic 3H-naphthopyran showing strong photocoloration |
title_short | Mechanistic insights into photochromic 3H-naphthopyran showing strong photocoloration |
title_sort | mechanistic insights into photochromic 3h naphthopyran showing strong photocoloration |
url | https://doi.org/10.1038/s41598-022-14679-9 |
work_keys_str_mv | AT błazejgierczyk mechanisticinsightsintophotochromic3hnaphthopyranshowingstrongphotocoloration AT michałfrode mechanisticinsightsintophotochromic3hnaphthopyranshowingstrongphotocoloration AT gotardburdzinski mechanisticinsightsintophotochromic3hnaphthopyranshowingstrongphotocoloration |