Design and synthesis of triptycene based fluorescent polymer with pendent triazole: Effect of functionality on host–guest interaction

Abstract

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 [Td > 289 °C and high char yield (>73%) at 800 °C]. Interestingly these new polymers (P2‐P5) are highly fluorescent in solution (Φ = 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 C60) has been investigated. The Stern–Volmer quenching constant (KSV) 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 C60, the KSV value decrease considerably in presence of 1,2,3‐triazole linked pendent. © 2017 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2017, 55, 3725–3735

Fluorescent Amorphous Distyrylnaphthalene-Based Polymers: Synthesis, Characterization and Thin-Film Nanomolar Sensing of Nitroaromatics in Water

“…Though the non-linear nature of the responses complicates the calculation of the limit of detection (LOD) by linear regression, we observe that 10% of the fluorescence was quenched by 50 nM concentrations of either PA or TNT, so the LOD should be below these concentration values (see insets in Figure 7). Thus, the sensitivities of P26 are among the best reported in the literature for polymeric solutions or films [25,36,37,38,39].…”

Conjugated polymers containing tetraphenylethylene in the backbones and side-chains for highly sensitive TNT detection

“…These values are among the best in the published literature. 23,29,49,50 The response of dispersed PTPA1-TPE nanoaggregates towards other aromatic analytes have been also tested, as shown in Fig. 6.…”

Ratiometric pH sensing by fluorescence resonance energy transfer-based hybrid semiconducting polymer dots in living cells

“…Nowadays, block polymers have been widely used in biomaterials, biosensors and drug delivery for their excellent biocompatibility and high hydrophilicity [23][24][25][26][27][28]. Fluorescent polymers, consisting of polymers and fluorescent molecules, have been extensively developed for their advantages over small molecular fluorescent probes [29][30][31][32].…”