Abstract
Reduction-responsive and anionic cyclophane (1) having a fluorescent pyrene moiety with a cleavable disulfide linkage was synthesized as a host-guest conjugate covalently bound with both host (cyclophane) and guest (pyrene) components. Reduction of the disulfide bond of 1 by glutathione gave its reduced forms (thiolates) of cyclophane and released pyrene derivatives that led to a significant fluorescence response in an aqueous carbonate buffer. The fluorescence intensity originating from monomer emission of 1 considerably decreased, accompanying increase of excimer emission due to self-aggregation of the resulting amphiphilic thiolate of pyrene derivative.
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