Synthesis of triptycene-derived covalent organic polymer networks and their subsequent in-situ functionalization with 1,2-dicarbonyl substituents

Three-dimensional polymer derivatives TP1–4 containing triptycene comonomers were synthesized from 1,4-diethynyl triptycene 1 with various di-, tri-, and tetra-brominated aromatic building blocks 3a-d through the mild Sonogashira cross-coupling reaction conditions. The abovementioned alkyne-containing copolymers were subsequently oxidized into their respective 1,2-diketone derivatives, OTP1–4, under mild reaction conditions. The UV–Vis and emission studies of copolymers TP1–4 and their oxidized homologues OTP1–4 confirmed the major influence of the aromatic substituent on the copolymer conjugation. Thermogravimetric analysis of copolymers TP1–4 revealed relatively high 10% weight loss temperature values (T _d ) reaching up to 490 °C. On the other hand, the 1,2-diketone containing target polymers OTP1–4 showed lower 10% weight loss temperature values T _d , with a maximum of 431 °C.