Structure and isomerization behavior relationships of new push-pull azo-pyrrole photoswitches.

Autor: Gallardo-Rosas D; Instituto de Ciencias Nucleares, UNAM, Circuito Exterior, Ciudad Universitaria, Coyoacán C.P. 04510, Ciudad de México, Mexico. carmen.ortega@nucleares.unam.mx., Guevara-Vela JM; Departamento de Química Física Aplicada, Universidad Autónoma de Madrid, 28049 Madrid, Spain., Rocha-Rinza T; Instituto de Química UNAM, Circuito Exterior, Ciudad Universitaria, Coyoacán C.P. 04510, Cuidad de México, Mexico., Toscano RA; Instituto de Química UNAM, Circuito Exterior, Ciudad Universitaria, Coyoacán C.P. 04510, Cuidad de México, Mexico., López-Cortés JG; Instituto de Química UNAM, Circuito Exterior, Ciudad Universitaria, Coyoacán C.P. 04510, Cuidad de México, Mexico., Ortega-Alfaro MC; Instituto de Ciencias Nucleares, UNAM, Circuito Exterior, Ciudad Universitaria, Coyoacán C.P. 04510, Ciudad de México, Mexico. carmen.ortega@nucleares.unam.mx.
Jazyk: angličtina
Zdroj: Organic & biomolecular chemistry [Org Biomol Chem] 2024 May 22; Vol. 22 (20), pp. 4123-4134. Date of Electronic Publication: 2024 May 22.
DOI: 10.1039/d4ob00417e
Abstrakt: A family of stilbenyl-azopyrroles compounds 2a-d and 3a-d was efficiently obtained via a Mizoroki-Heck C-C-type coupling reaction between 2-(4'-iodophenyl-azo)- N -methyl pyrrole (1a) and different vinyl precursors. The influence of the π-conjugated backbone and the effect of the pyrrole moiety were correlated with their optical properties. Studies via UV-Visible spectrophotometry revealed that the inclusion of EWG or EDG favors a red-shift of the main absorption band in these azo compounds compared with their non-substituted analogues. Furthermore, there is a clear influence between the half-life of the Z isomer formed by irradiation with white light and the push-pull behavior of the molecules. In several cases, the stilbenyl-azopyrroles led to the formation of J-type aggregates in binary MeOH : H 2 O solvents, which are of interest for water compatible applications.
Databáze: MEDLINE
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