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OFF-ON Fluorescence Sensing of Fluoride by Donor-Antimony(V) Lewis Acids

A series of triarylmethylstibonium Lewis acids of general formula [Ph2MeSb-(p-(C6H4))-FLUO]+ bearing a peripheral electron rich fluorophore (FLUO = 10H-phenoxazine ([3a]+), diphenylamine ([3b]+), and 9H-carbazole ([3c]+)) have been synthesized and investigated for the fluorescence turn-on sensing of fluoride anions. Treatment of the stibonium cations with fluoride anions leads to the corresponding fluorostiboranes (3a-F?3c-F). While the stibonium cations are almost non-emissive, the fluorostiboranes display fluorophore-centered emissions arising from the corresponding ???* excited state. The carbazole containing derivative [3c]+ exhibits the most intense fluorescence turn-on response. It also displays a high binding constant (K > 107 M?1) in MeCN and shows compatibility with protic media such as MeOH (K = 950(?50) M-1). Computational studies aimed at identifying the origin of the turn-on response show that the excited state of the stibonium cations is best described as charge transfer in nature with the ?-system of the fluorophore acting as the donor and the ?*??* system of the stibonium unit acting as the acceptor. This ?(FLUO)??*/?*[Ph2MeSb-(p-(C6H4))] excited state is non-emissive making these cations dark in the absence of fluoride anions. Conversion to the fluorostiboranes occurs via donation of a fluoride lone pair into the antimony-centered ?*. Formation of this Sb?F bond modifies the electronic structure of the platform and restores the emissive ???* excited state of the fluorophore thus accounting for the observed OFF-ON fluorescence response.

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