Two o-carborane-based π-conjugated macrocycles are synthesized via oxidative coupling of acetylene-terminated o-carborane precursors. The single-crystal X-ray diffraction analysis unambiguously revealed their unique porous supramolecular structures, which display micropore characteristics. The novel macrocycles possess aggregation-induced emission both in aggregate state and solid state. This work provides a new design strategy for developing o-carborane macrocyclic molecules with excellent photophysical properties. Based on the obvious fluorescence quenching phenomenon of macrocycle by 1,4-dinitrobenzene and 2,4,6-trinitrophenol, the macrocyclic compounds have promising potential as sensors for nitroaromatics.

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