Fluorescent materials have emerged as one of the promising candidates for chemical sensing due to their high sensitivity towards analytes that are relatively electron deficient such as nitroaromatics (NACs). Herein, four new 1,2,3-triazole functionalized dibromo monomers (2-5) have been synthesized. These dibromo monomers (2-5) have been subsequently polymerized with 2,6-diethynyltriptycene (DET) to yield four new ethynyl linked polymers (P2-P5) with 1,2,3-triazole pendent. These polymers are organosoluble, amorphous in nature and have high thermal stability [T-d>289 degrees C and high char yield (>73%) at 800 degrees C]. Interestingly these new polymers (P2-P5) are highly fluorescent in solution (phi=0.37-0.43 in DCM) relative to the polymer (P1) that does not have the 1,2,3-triazole motif as a pendent. The host-guest interaction between these polymers (P1-P5) and electron deficient molecules (PA and C-60) has been investigated. The Stern-Volmer quenching constant (K-SV) data suggest that the interaction of picric acid and polymers increases significantly in presence of 1,2,3-triazole linked pendent group whereas in case of C-60, the K-SV value decrease considerably in presence of 1,2,3-triazole linked pendent. (C) 2017 Wiley Periodicals, Inc