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 (<i>T</i>_d) > 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