Organic π-conjugated materials that incorporate the benzo[1,2-b:4,5-b′]dithiophene (BDT) building block have garnered significant attention over recent years. In this time, the BDT heterocycle has primarily been modified with respect to the benzene core (the 3,6-positions) to modulate its electronic and solubility properties, where most of the synthetic alterations include “static” alkyl and alkoxy groups. We envisioned possible “dynamic” and tunable BDT derivatives could be created from benzo[1,2-b:4,5-b']dithiophen-4-ol (BDT-OH), first synthesized and studied (with respect its tautomerism) in the 1970s by MacDowell and coworkers. In this work, we reexamine the properties of BDT-OH in solution and the solid state, and introduce novel π-extended analogues. While parent BDT-OH can undergo various irreversible chemical oxidation reactions in solution, the π-extended systems produce only one major dimerization product under the same conditions.

Revisiting and extending the chemical and functional behavior of benzo[1,2-b:4,5-b']dithiophen-4-ol

254th National Meeting (2017)

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