Blending the Optical and Redox Properties of Oligoynes and Boron Difluoride Formazanates

Abstract

Oligoynes and polyynes are 1D chains of conjugated sp-hybridized carbon atoms consisting of alternating single and triple bonds. Their stability rapidly decreases with increasing chain length beyond only a few repeating units. Design strategies, such as the use of bulky end-capping groups, allow for their characterization and isolation while not contributing significantly to their physical properties. In this study, we incorporate redox-active BF 2 formazanate dyes (BF 2 ) as end-caps to prepare symmetric (BF 2 À [C�C] n À BF 2 ) and asymmetric (BF 2 À [C�C] n À Si(iPr) 3 ) families of oligoynes containing up to 10 alkyne units. In doing so, we introduce stable oligoynes that possess a blend of optical and redox properties that cannot be achieved by either oligoynes or BF 2 formazanates individually (e.g., panchromatic absorption, multiple and tunable reversible redox waves). This approach is transferable to other functional end-caps to facilitate the preparation of π-conjugated materials with utility in the organic electronics arena.