Journal of Organic Chemistry
Journal of Organic Chemistry
3 years ago

Pulling with the Pentafluorosulfanyl Acceptor in Push–Pull Dyes

Pulling with the Pentafluorosulfanyl Acceptor in Push–Pull Dyes
Julian M. W. Chan, Victoria E. Hillier, Prabhat Gautam, Guoxian Zhang, Craig P. Yu
A new class of push–pull fluorophores featuring the pentafluorosulfanyl (SF5) group as a potent acceptor has been synthesized. Known for its excellent chemical and thermal stability, the unique SF5 functionality is also strongly electron-withdrawing but at the same time highly lipophilic. We report six new fluorescent dyes, which were characterized by UV–vis/fluorescence spectroscopy, single-crystal X-ray diffraction, and cyclic voltammetry. Notable dye properties include large Stokes shifts (>100 nm), pronounced solvatofluorochromic effects arising from intramolecular charge transfer, moderate fluorescence quantum yields in both solutions and thin films, and extensive supramolecular C–H···F interactions in their crystalline states. Reversible mechanofluorochromism was also observed in dye 5, where grinding and fuming of a solid sample gave blue- and red-shifted emissions, respectively. Postfunctionalization of dye 3 to afford a pair of strong visible-light absorbers was also demonstrated.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b01972

DOI: 10.1021/acs.joc.7b01972

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