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

Authors

Jasveer S. Dhindsa
Erin L. Cotterill
Francis L. Buguis
Michael Anghel
Paul D. Boyle
Joe B. Gilroy, Univeristy of Western OntarioFollow

Document Type

Article

Publication Date

Summer 7-20-2022

Journal

Angewandte Chemie International Edition

URL with Digital Object Identifier

https://doi.org/10.1002/anie.202208502

Abstract

Oligoynes and polyynes are 1-D 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 BF₂ formazanate dyes (BF₂) as end-caps to prepare symmetric (BF₂−[C≡C]_n−BF₂) and asymmetric (BF₂−[C≡C]_n−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 BF₂ 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.