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Synthesis, Fluorescence, and Two‐Photon Absorption Properties of Push–Pull 5‐Arylthieno[3,2‐ b ]thiophene Derivatives
Author(s) -
Manuela M.,
Raposo M.,
Herbivo Cyril,
Hugues Vincent,
Clermont Guillaume,
Castro M. Cidália R.,
Comel Alain,
BlanchardDesce Mireille
Publication year - 2016
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201600806
Subject(s) - photochemistry , chemistry , thiophene , knoevenagel condensation , intramolecular force , chromophore , fluorescence , moiety , two photon absorption , suzuki reaction , acceptor , absorption (acoustics) , electron donor , delocalized electron , organic chemistry , aryl , materials science , laser , physics , alkyl , quantum mechanics , optics , composite material , condensed matter physics , catalysis
Three series of novel push–pull 5‐arylthieno[3,2‐ b ]thiophene derivatives functionalized with potent electron‐withdrawing terminal moieties have been synthesized in moderate to excellent yields by Suzuki coupling followed by Knoevenagel condensation. These novel chromophores show intense absorption in the near‐UV region through to the orange visible region, related to a strong intramolecular charge‐transfer transition. By combining a strong donor and acceptor, large fluorescence quantum yields were achieved as well as large two‐photon absorption responses. Interestingly, due to the improved rigidity and electronic delocalization provided by the thienothiophene moiety (as compared with the bithiophene unit), higher one‐ and two‐photon brightness values have been achieved. As a result, several new fluorescent dyes showing enhanced brightness and tunable fluorescence (ranging from the blue to the NIR region) have been obtained that have potential for bioimaging applications.