Terpyridine-attached phthalonitrile (Pn-TP) linked by cyanovinyl bond has been synthesized and employed for the preparation of subphthalocyanine (SubPc-TP) bearing conjugated terpyridine moieties. Both Pn-TP and SubPc-TP exhibited highly selective fluorescence turn-on in the presence of cyanide anions (CN) based on chemodosimetric sensing mechanism. The conjugation of the Pn-TP molecule was interrupted by the addition of CN at the cyanovinyl bond, showing the ratiometric fluorescence turn-on behavior. This sensing mechanism was further supported by density functional theory calculation and nuclear magnetic resonance titration studies. Optical and photophysical responses of SubPc-TP towards CN were also investigated, in which similar fluorescence enhancement was observed due to the addition of CN at the reactive boron trimer. The detection limit was estimated to be 94 nM, much below the World Health Organization-allowed level (1.9 μM) of CN in water.
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