Efficient Synthesis of a Complete Donor/Acceptor bis (Aryl)diyne Family

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Synthetic Communications, ISSN: 0039-7911, Vol: 33, Issue: 14, Page: 2447-2461

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Holmes, Brian T.; Pennington, William T.; Hanks, Timothy W.
Informa UK Limited
Chemistry; Charge-transfer; Cross-coupling; Diacetylene
article description
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 bromophenyl-acetylene, 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.