We report here the synthesis of 1,2-bis(3,5-dimethyl-4-pyridyl)acetylene-N,N’-dioxide as an electron rich donor species. The electron donor molecule was synthesized in four steps by first reacting 4-bromo-2,5-dimethylpyridine with trimethylsilyl acetylene under Sonogashira coupling conditions. Deprotection of the resulting silyl acetylene gave 3,5-dimethyl-4-pyridylacetylene in good yield. The terminal alkyne was then subjected to another palladium Sonogashira coupling reaction using 4-bromo-2,5-dimethylpyridine to afford 1,2-bis(3,5-dimethyl-4-pyridyl)acetylene. The N,N’-dioxide was then produced using Oxone®. As an electron rich donor, the dioxide should co-crystallize with electron poor acceptor species such as tetracyanoethylene (TCNE) or 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ).

Synthesis of 1,2-bis(3,5-dimethyl-4-pyridyl)acetylene-N,N’-dioxide as a donor for the preparation of donor/acceptor cocrystals

2019 Spring National Meeting

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