Efficient Synthesis of a Complete Donor/Acceptor bis (Aryl)diyne Family
Holmes, B. T.; Pennington, W. T.; Hanks, T. W. Efficient Synthesis of a Complete Donor/Acceptor bis (Aryl)diyne Family. Synth. Commun. 2003, 33, 2447-2461.
A facile route to a family of bis(aryl)diynes containing both an electron donating pyridine ring and an electron accepting iodobenzene has been developed. The convergent synthesis involves the coupling of 2-, 3-, or 4-bromopyridine with TMS-acetylene, followed by deprotection to form the first half of the molecule. Similarly, 2-, 3-, or 4-iodoaniline was coupled to TMS-acetylene after protection of the amine group as a diethyltriazine. After conversion of the triazine to an iodine, deprotection of the acetylene and formation of the corresponding bromophenylacetylene, the two halves of the molecule were coupled under Cadiot-Chodkiewicz conditions. Nine new compounds were prepared, each of which was found to thermally polymerize from the melt. None of the compounds underwent photochemical polymerization in the solid-state.