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Synthesis, fluorescence and two-photon absorption properties of push-pull 5-aryl[3,2-b]thienothiophene derivatives

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Resumo:Three series of novel push-pull 5-aryl[3,2-b]thienothiophene derivatives functionalized with potent electron-withdrawing terminal moieties) were synthesized in moderate to excellent yields through Suzuki coupling followed by Knoevenagel condensation. These novel chromophores combine intense absorption in the near-UV down to the orange visible region in relation with a strong intramolecular charge transfer transition. By combining strong donor and acceptor, large fluorescence quantum yield are achieved as well as large two-photon absorption responses. Interestingly, due to the improved rigidity and electronic delocalization provided by the thienothiophene moiety (compared to the bis-thiophene one) larger one- and two-photon brightness values are achieved. As a result, a library of new fluorescent dyes showing enhanced brightness (up to and tunable fluorescence (ranging from blue to the NIR region) has been obtained which offer interesting promises for bioimaging applications.
Autores principais:Raposo, M. Manuela M.
Outros Autores:Herbivo, Cyril; Hugues, Vincent; Clermont, Guillaume; Castro, M. Cidália R.; Comel, Alain; Blanchard-Desce, Mireille
Assunto:Synthesis Fluorescence Two-photon absorption (TPA) Thienothiophenes Push-pull heterocyclic systems Nonlinear optics (NLO) Suzuki coupling Bioimaging applications Aldehydes Cross-coupling Donor-acceptor systems Sulfur heterocycles Two-photon absorption
Ano:2016
País:Portugal
Tipo de documento:artigo
Tipo de acesso:acesso aberto
Instituição associada:Universidade do Minho
Idioma:inglês
Origem:RepositóriUM - Universidade do Minho
Descrição
Resumo:Three series of novel push-pull 5-aryl[3,2-b]thienothiophene derivatives functionalized with potent electron-withdrawing terminal moieties) were synthesized in moderate to excellent yields through Suzuki coupling followed by Knoevenagel condensation. These novel chromophores combine intense absorption in the near-UV down to the orange visible region in relation with a strong intramolecular charge transfer transition. By combining strong donor and acceptor, large fluorescence quantum yield are achieved as well as large two-photon absorption responses. Interestingly, due to the improved rigidity and electronic delocalization provided by the thienothiophene moiety (compared to the bis-thiophene one) larger one- and two-photon brightness values are achieved. As a result, a library of new fluorescent dyes showing enhanced brightness (up to and tunable fluorescence (ranging from blue to the NIR region) has been obtained which offer interesting promises for bioimaging applications.