Redox‐Active Heteroatom‐Functionalized Polyacetylenes
| Autor: | Bruno T. Luppi, Eric Rivard, I T. Cheong, Michael J. Ferguson, Nils Ostermann, Inke Siewert, Abhishek V. Muralidharan |
|---|---|
| Rok vydání: | 2021 |
| Předmět: |
Chemistry
010405 organic chemistry Heteroatom Chemical modification General Chemistry ROMP General Medicine Metathesis 010402 general chemistry Combinatorial chemistry 01 natural sciences Catalysis 0104 chemical sciences Polyacetylene chemistry.chemical_compound Polymerization Click chemistry Side chain |
| Zdroj: | Angewandte Chemie. 134 |
| ISSN: | 1521-3757 0044-8249 |
| DOI: | 10.1002/ange.202114586 |
| Popis: | 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 (-BR2) and phosphoryl (-P(O)R2) side chains; (2) electron-donating amino (-NR2) 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. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|