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Cascade Cyclopolymerization of 5-Ethynyl-1,8-Nonadiyne Derivatives to Synthesize Low Band Gap Conjugated Polyacetylenes Containing Fused Bicyclic Structure

Ryu, Hanseul and Sung, Jong-Chan and Kim, Gangme and Xu, Yan and Grubbs, Robert H. and Choi, Tae-Lim (2022) Cascade Cyclopolymerization of 5-Ethynyl-1,8-Nonadiyne Derivatives to Synthesize Low Band Gap Conjugated Polyacetylenes Containing Fused Bicyclic Structure. Angewandte Chemie International Edition, 61 (45). ISSN 1433-7851. doi:10.1002/anie.202210244. https://resolver.caltech.edu/CaltechAUTHORS:20221017-15547800.34

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Abstract

Cyclopolymerization is a powerful method for synthesizing polyacetylenes containing four- to seven-membered rings. However, the structure of the repeat unit only consists of mono-cycloalkene due to the single cyclization of diyne monomers. Herein, we demonstrate a novel cascade cyclopolymerization to synthesize polyacetylenes containing fused bicyclic rings from triyne monomers containing bulky dendrons via sequential cascade ring-closing metathesis. These dendrons provided solubility and stability to the rigid bicyclic polyacetylene backbone. In addition, we controlled the regioselectivity of the catalyst approach by altering its structure and synthesized polymers containing fused bicyclo[4,3,0] or [4,4,0] rings with high molecular weights of up to 120 kg mol⁻¹. Interestingly, the resulting polymers showed narrower band gaps (down to 1.6 eV) than polymers with mono-cycloalkene repeat units due to the planarization of the conjugated segment resulting from the fused bicyclic structure.


Item Type:Article
Related URLs:
URLURL TypeDescription
https://doi.org/10.1002/anie.202210244DOIArticle
ORCID:
AuthorORCID
Ryu, Hanseul0000-0003-4846-3488
Xu, Yan0000-0003-2808-7964
Grubbs, Robert H.0000-0002-0057-7817
Choi, Tae-Lim0000-0001-9521-6450
Additional Information:We are thankful for financial support from the Creative Research Initiative Grant through NRF, Korea.
Funders:
Funding AgencyGrant Number
National Research Foundation of KoreaCreative Research Initiative Grant
Issue or Number:45
DOI:10.1002/anie.202210244
Record Number:CaltechAUTHORS:20221017-15547800.34
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20221017-15547800.34
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:117472
Collection:CaltechAUTHORS
Deposited By: Research Services Depository
Deposited On:25 Oct 2022 20:03
Last Modified:08 Nov 2022 00:09

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