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

David Gallardo-Rosas; Jose Manuel Guevara-Vela; Tomás Rocha-Rinza; R. A. Toscano; José G. López-Cortés; M. Carmen Ortega-Alfaro

doi:10.1039/d4ob00417e

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

David Gallardo-Rosas, Jose Manuel Guevara-Vela, Tomás Rocha-Rinza, R. A. Toscano, José G. López-Cortés, M. Carmen Ortega-Alfaro^*

^*Corresponding author for this work

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

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Abstract

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 : H2O solvents, which are of interest for water compatible applications.

Original language	English
Pages (from-to)	4123-4134
Number of pages	12
Journal	Organic and Biomolecular Chemistry
Volume	22
DOIs	https://doi.org/10.1039/d4ob00417e
Publication status	Published - 30 Apr 2024

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "Structure and isomerization behavior relationships of new push-pull azo-pyrrole photoswitches",

abstract = "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 : H2O solvents, which are of interest for water compatible applications.",

author = "David Gallardo-Rosas and Guevara-Vela, \{Jose Manuel\} and Tom{\'a}s Rocha-Rinza and Toscano, \{R. A.\} and L{\'o}pez-Cort{\'e}s, \{Jos{\'e} G.\} and Ortega-Alfaro, \{M. Carmen\}",

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doi = "10.1039/d4ob00417e",

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T1 - Structure and isomerization behavior relationships of new push-pull azo-pyrrole photoswitches

AU - Gallardo-Rosas, David

AU - Guevara-Vela, Jose Manuel

AU - Rocha-Rinza, Tomás

AU - Toscano, R. A.

AU - López-Cortés, José G.

AU - Ortega-Alfaro, M. Carmen

PY - 2024/4/30

Y1 - 2024/4/30

N2 - 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 : H2O solvents, which are of interest for water compatible applications.

AB - 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 : H2O solvents, which are of interest for water compatible applications.

UR - https://www.scopus.com/pages/publications/85192434013

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DO - 10.1039/d4ob00417e

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AN - SCOPUS:85192434013

SN - 1477-0520

VL - 22

SP - 4123

EP - 4134

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

ER -

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

Abstract

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