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Synthesis and Photodynamics of Stilbenyl‐Azopyrroles: Two‐Photon Controllable Photoswitching Systems
Author(s) -
MuñozRugeles Leonardo,
GallardoRosas David,
DuránHernández Jesús,
LópezArteaga Rafael,
Toscano R. Alfredo,
EsturauEscofet Nuria,
LópezCortés José G.,
Peón Jorge,
OrtegaAlfaro M. Carmen
Publication year - 2020
Publication title -
chemphotochem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.13
H-Index - 18
ISSN - 2367-0932
DOI - 10.1002/cptc.201900185
Subject(s) - photoisomerization , isomerization , excitation , photochemistry , chemistry , two photon excitation microscopy , molecule , photochromism , absorption (acoustics) , azobenzene , pyrrole , optics , physics , organic chemistry , catalysis , quantum mechanics
Three new stilbenyl‐azopyrroles 3 a – c were synthesized through a Mizoroki‐Heck C−C‐type coupling reaction between the 2‐(4′‐iodophenyl‐azo)‐ N ‐methyl pyrrole ( 1 ), and three different para ‐substituted styrene derivatives. Inclusion of additional NO 2 and NMe 2 groups at the para‐ position of the stilbenyl section resulted in significant changes of their linear and non‐linear optical properties. The photoisomerization behavior was studied through ultrafast laser techniques for single‐ and two‐photon excitation. The time‐resolved studies indicate that, despite the drastic changes in conjugation, the typical path for photoisomerization is maintained in these systems for both single and biphotonic excitation. In particular, the NO 2 substituted molecule showed improved two‐photon absorption capacities, together with a significant trans − cis isomerization channel, implying that the photoswitching process can be controlled with high spatial precision through non‐linear optical excitation.