6-Arylcoumarin as a Scaffold of Photofunctional Molecules with OFF-ON-OFF Type Regulation.
J Org Chem
; 86(3): 2264-2270, 2021 02 05.
Article
em En
| MEDLINE
| ID: mdl-33356259
ABSTRACT
Coumarin has been utilized as a core structure of photofunctional molecules, such as fluorescent sensors and photoremovable protecting groups. Here, we show that the 6-arylcoumarin moiety can provide OFF-ON-OFF type regulatory functionality for such compounds. To illustrate its utility, we synthesized a coumarin derivative bearing two phenolic hydroxy groups at 7-position and on 6-aryl group as a fluorescent sensor showing an OFF-ON-OFF change in fluorescence intensity in response to an increase in pH from a strongly acidic condition. Further, we show that the efficiency of photoreaction of other derivatives with the same hydroxyl groups is switched from "OFF" at pH 3 and 6 to "ON" at pH 9 and then to OFF at pH 12, enabling their application as switchable photoremovable protective groups. These features arise from sequential deprotonation of two hydroxyl groups the monoanionic form is responsible for the photoinduced fluorescence and photoreaction.
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1
Base de dados:
MEDLINE
Assunto principal:
Corantes Fluorescentes
Idioma:
En
Ano de publicação:
2021
Tipo de documento:
Article