Redox-Active Heteroatom-Functionalized Polyacetylenes.

Autor: Luppi BT; Department of Chemistry, University of Alberta, 11227 Saskatchewan Dr, Edmonton, Alberta, T6G 2G2, Canada., Muralidharan AV; Department of Chemistry, University of Alberta, 11227 Saskatchewan Dr, Edmonton, Alberta, T6G 2G2, Canada., Ostermann N; University of Goettingen, Institute of Inorganic Chemistry, Tammannstrasse 4, 37077, Goettingen, Germany., Cheong IT; Department of Chemistry, University of Alberta, 11227 Saskatchewan Dr, Edmonton, Alberta, T6G 2G2, Canada., Ferguson MJ; Department of Chemistry, University of Alberta, 11227 Saskatchewan Dr, Edmonton, Alberta, T6G 2G2, Canada., Siewert I; University of Goettingen, Institute of Inorganic Chemistry, Tammannstrasse 4, 37077, Goettingen, Germany., Rivard E; Department of Chemistry, University of Alberta, 11227 Saskatchewan Dr, Edmonton, Alberta, T6G 2G2, Canada.
Jazyk: angličtina
Zdroj: Angewandte Chemie (International ed. in English) [Angew Chem Int Ed Engl] 2022 Jan 21; Vol. 61 (4), pp. e202114586. Date of Electronic Publication: 2021 Dec 15.
DOI: 10.1002/anie.202114586
Abstrakt: The discovery of metallic conductivity in polyacetylene [-HC=CH-] n upon doping represents a landmark achievement. However, the insolubility of polyacetylene and a dearth of methods for its chemical modification have limited its widespread use. Here, we employ a ring-opening metathesis polymerization (ROMP) protocol to prepare functionalized polyacetylenes (fPAs) bearing: (1) electron-deficient boryl (-BR 2 ) and phosphoryl (-P(O)R 2 ) side chains; (2) electron-donating amino (-NR 2 ) groups, and (3) ring-fused 1,2,3-triazolium units via strain-promoted Click chemistry. These functional groups render most of the fPAs soluble and can lead to intense light absorption across the visible to near-IR region. Also, the presence of redox-active boryl and amino groups leads to opposing near-IR optical responses upon (electro)chemical reduction or oxidation. Some of the resulting fPAs show greatly enhanced air stability when compared to known polyacetylenes. Lastly, these fPAs can be cross-linked to yield network materials with the full retention of optical properties.
(© 2021 Wiley-VCH GmbH.)
Databáze: MEDLINE
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