Photobehavior and Nonlinear Optical Properties of Push-Pull, Symmetrical, and Highly Fluorescent Benzothiadiazole Derivatives
Anno: 2016
Autori: Ricci F., Elisei F., Foggi P., Marrocchi A., Spalletti A., Carlotti B.
Affiliazione autori: Univ Perugia, Dept Chem Biol & Biotechnol, Via Elce Sotto 8, I-06123 Perugia, Italy; Univ Perugia, CEMIN, Via Elce Sotto 8, I-06123 Perugia, Italy; LENS, Via Nello Carrara 1, I-50019 Florence, Italy; INO CNR, Largo Fermi 6, I-50125 Florence, Italy.
Abstract: Three quadrupolar D-pi-A-pi-D compounds, bearing alkoxy phenyls as mild electron donors and a benzothiadiazole (A), two benzothiadiazoles (B), or a benzothiadiazole linked to two thiophenes (C) as the acceptor units, are collectively the object of this study. They proved to be efficient yellow/orange/red fluorophores, respectively, with fluorescence being their preferred deactivation pathway. These systems exhibited positive fluorosolvatochromism and a noticeable decrease of the fluorescence quantum yield in the most polar solvent (with the quenching following the trend B > A > C). These findings point to an intramolecular charge transfer (ICT) nature of the emitting state, whose photoinduced dynamics was investigated by femtosecond-resolved transient absorption and fluorescence upconversion. Remarkable values of hyperpolarizability were estimated by the solvatochromic method. The significant two-photon absorption cross sections measured for A-C (whose trend nicely parallels that of ICT efficiency), coupled. with the intense emission, make them promising for applications as environment-sensitive probes in two-photon excited fluorescence imaging.
Giornale/Rivista: JOURNAL OF PHYSICAL CHEMISTRY C
Volume: 120 (41) Da Pagina: 23726 A: 23739
Maggiori informazioni: We acknowledge support from the Italian Ministero per l�Universita e la Ricerca Scientifica e Tecnologica, MIUR (Rome, Italy) under the FIRB Futuro in Ricerca 2013, no. RBFR13PSB6. Dr. Rebecca Flamini is kindly acknowledged for previous experimental work and useful discussions that inspired this work.
Parole chiavi: Charge transfer; Fluorescence; Fluorophores; Nonlinear optics; Optical properties; Photons; Two photon processes, Benzothiadiazole derivatives; Fluorescence quantum yield; Fluorescence upconversion; Intramolecular charge transfers; Non-linear optical properties; Solvatochromic methods; Two-photon absorption cross section; Two-photon excited fluorescence, C (programming language)
DOI: 10.1021/acs.jpcc.6b07290
Citazioni: 61
dati da “WEB OF SCIENCE” (of Thomson Reuters) aggiornati al: 2025-06-01
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