Synthesis of Triptycene-Based Organosoluble, Thermally Stable, and Fluorescent Polymers: Efficient Host–Guest Complexation with Fullerene

Abstract

We report a facile synthesis of 2,6-diethynyltriptycene (DET) in high yield. Application of DET as monomer in polymer chemistry has been shown (for the first time) in syntheses of two novel polymers via Sonogashira cross-coupling reaction in high yield. The newly synthesized polymers were characterized by FT-IR, UV–vis absorption, and NMR spectroscopic techniques. The polymers prepared using DET have interesting properties such as high solubility in common organic solvents, high thermal stability [decomposition temperatures (Td) > 495 °C], and high char yield (greater than 81% at 900 °C). Additionally, polymers are fluorescent. Host–guest interaction between triptycene-based polymers and fullerene (C60) has been studied for the first time. Fluorescence quenching of our polymers by C60 has been used to study the extent of (polymer·C60) host–guest complex formation. Fluorescence quenching studies indicate binding constant for polymer·C60 complexation on the order of 105 M–1.