An Efficient Ag⁺-Selective Fluorescent Chemosensor Derived from Tribenzotriquinacene

Abstract

A new C _3v -symmetrical tribenzotriquinacene (TBTQ) derivative bearing six 8-quinolinyloxymethyl units at the rim of the bowl-shaped molecular framework is synthesized in a single-step by six-fold etherification of the corresponding hexakis(chloromethyl)-TBTQ precursor with 8-hydroxyquinoline. The resulting compound acts as a fluorescence chemosensor, producing a ‘turn-off’ fluorescent quenching response in the presence of Ag⁺ ions, and is highly selective toward Ag⁺ over other cations, such as Al³⁺, Ca²⁺, Cd²⁺, Co²⁺, Cr³⁺, Cu²⁺, Fe³⁺, Ga³⁺, Hg²⁺, In³⁺, K⁺, Mg²⁺, Mn²⁺, Na⁺, Ni²⁺, Pb²⁺, Pd²⁺, and Zn²⁺. The fluorescence intensity change of the chemosensor solution can be clearly observed by the naked eye upon addition of silver salts.

Key words

tribenzotriquinacenes - 8-quinolinyloxy derivatives - fluorescent chemosensors - chemoselectivity - silver ions

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