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Two new triptycene-based azobenzene-functionalized polymers ( TBAFPs ) have been synthesized using the well-known Pd-catalyzed Sonogashira cross-coupling polycondensation reaction between 2,6-diethynyltriptycene and ( meta or para ) dibromo-azobenzenes. Enhancement of the fluorescent emission intensity was observed upon trans → cis isomerization of -N=N- linkage in TBAFPs . The cis-lifetime of TBAFP1 is rather long (greater than 2 days). The resulting materials were tested as a potential chemosensor for the detection of picric acid (PA)-a water pollutant as well as chemical constituent of explosives used in warfare. PA was found to interact strongly with TBAFPs , which led to significant quenching of the latter's fluorescence emission intensities. The binding constants are in the order of 10 5 M -1 . TBAFPs were also able to detect PA in nanomolar concentrations.

Triptycene-Derived Photoresponsive Fluorescent Azo-Polymer as Chemosensor for Picric Acid Detection