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

• Autor(a) principal: Raposo, M. Manuela M.
• Data de Publicação: 2016
• Outros Autores: Herbivo, Cyril, Hugues, Vincent, Clermont, Guillaume, Castro, M. Cidália R., Comel, Alain, Blanchard-Desce, Mireille
• Tipo de documento: Artigo
• Idioma: eng
• Título da fonte: Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
• Texto Completo: http://hdl.handle.net/1822/44251
• topic: 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; Ciências Naturais::Ciências Químicas; Science & Technology

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.