Work

Pulling with the Pentafluorosulfanyl Acceptor in Push–Pull Dyes

Year: 2017

Type: article

Abstract: 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.

Source: The Journal of Organic Chemistry

DOI: 10.1021/acs.joc.7b01972

Authors: Prabhat Gautam, Craig P. Yu, Guoxian Zhang, Victoria E. Hillier, Julian M. W. Chan

Institution: University of Ottawa

Language: English

Topic: Luminescence and Fluorescent Materials

Subfield: Materials Chemistry

Field: Materials Science

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $4,500

Funders: University of Ottawa, Canada Foundation for Innovation, Ontario Ministry of Research, Innovation and Science, Natural Sciences and Engineering Research Council of Canada