Thiophene-based polymers have evolved as some of the most successful materials for organic electronic applications. The structural variation of oligo- and polythiophenes allows a broad electronic and chemical tuning range. Our project aims to study electronic, electrochromic, redox, and optical properties of thiophene-based materials integrated with organometallic systems such as ferrocene. We begin by converting 1,2-bis(hydroxymethyl)ferrocene to 1,2-bis(thiouroniummethyl)ferrocene with thiourea under acidic conditions. Refluxing the salt in base followed by acidification results in 1,2-bis(mercaptomethyl)ferrocene, which is oxidized to the cyclic 1,4-dihydro-2,3-ferrocenodithiin. Ring contraction of the cyclic dithiin gives the thioether, 1,3-dihydroferroceno[c]thiophene. Periodate oxidation gives 1,3-dihydroferrroceno[c]thiophene-2-oxide (1  ), a potential precursor for ferroceno[c]thiophene via Pummerer dehydration. Dehydration of 1  and in situ trapping of the resulting thiophene are under study. Besides the sulfur system, we have also been looking into synthetic routes to ferrocene-fused furan and ferrocene-fused pyrrole. Recent renewed interest into a-oligofurans for organic electronics encourages investigation into these heteroatom systems as well.

Ferrocene-fused heterocyclic systems

248th National Meeting (2014)

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