Journal
JOURNAL OF PHYSICAL CHEMISTRY C
Volume 120, Issue 41, Pages 23726-23739Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.jpcc.6b07290
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Funding
- Italian Ministero per l'Universita e la Ricerca Scientifica e Tecnologica, MIUR (Rome, Italy) under FIRB Futuro in Ricerca [RBFR13PSB6]
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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.
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