Blockade of persistent colored isomer formation in photochromic 3H-naphthopyrans by excited-state intramolecular proton transfer.
Journal
Scientific reports
ISSN: 2045-2322
Titre abrégé: Sci Rep
Pays: England
ID NLM: 101563288
Informations de publication
Date de publication:
10 Nov 2022
10 Nov 2022
Historique:
received:
18
08
2022
accepted:
04
11
2022
entrez:
10
11
2022
pubmed:
11
11
2022
medline:
11
11
2022
Statut:
epublish
Résumé
In photochemistry the excited-state intramolecular proton transfer process (ESIPT) is often observed as a highly efficient singlet excited state depletion pathway, which in the presence of a strong intramolecular hydrogen bond may proceed on a subpicosecond time scale. The present work describes the suppression of unwanted transoid-trans isomer formation in photochromic 3H-naphthopyran derivatives by the introduction of a 5-hydroxy substituent. According to time-resolved spectroscopy experiments and excited-state ab initio calculations, transoid-cis → transoid-trans photoisomerization is reduced by a competitive ESIPT channel in nonpolar solvent (cyclohexane). Upon specific solute-solvent interactions (methanol, acetonitrile) the intramolecular hydrogen bond in the transoid-cis form is perturbed, favoring the internal conversion S
Identifiants
pubmed: 36357476
doi: 10.1038/s41598-022-23759-9
pii: 10.1038/s41598-022-23759-9
pmc: PMC9649631
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
19159Subventions
Organisme : National Science Centre (NCN), Poland
ID : 2017/27/B/ST4/00320
Organisme : Polish-U.S. Fulbright Commission
ID : US/2021/31/SC
Informations de copyright
© 2022. The Author(s).
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