Synthesis of Conjugated Polymers: Comparing the Indophenine Reaction with Traditional Methods
Date
2024-07-10
Authors
Berbigier, Jônatas Faleiro
Kelly, Timothy L.
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American Chemical Society
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Article
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Abstract
Conjugated polymers are an important class of materials whose development underpins many recent advances in organic electronics. Traditionally, these polymers have been synthesized by transition metal-catalyzed cross-couplings using organometallic reagents (e.g., Stille couplings). Although direct heteroarylation polymerization (DHAP) dispenses with the organometallic intermediates, DHAP is still a metal-catalyzed coupling, requiring both catalyst optimization and purification to remove trace metal contaminants. In contrast, a recent report from our group demonstrated that the indophenine reaction can be used as a metal-free method to prepare conjugated polymers; however, from this initial proof-of-concept study, it was not clear how it compared to other methods of conjugated polymer synthesis. Therefore, in this report, we synthesized the same polymer using three distinctly different approaches: Stille coupling, DHAP, and the indophenine reaction. This allows us to directly compare the three methodologies; we find that each offers distinct trade-offs in terms of atom economy, defects, and molecular weight.
Description
This document is the Accepted Manuscript version of a Published Work that appeared in final form in ACS Applied Polymer Materials, copyright © 2024 American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see J. Faleiro Berbigier, and T. L. Kelly* Synthesis of Conjugated Polymers: Comparing the Indophenine Reaction with Traditional Methods. ACS Applied Polymer Materials. 2024, 6, 8318-8325. https://doi.org/10.1021/acsapm.4c01169.
Keywords
indophenine, π-conjugated polymers, polymerizations, conducting polymers, organic semiconductors
Citation
J. Faleiro Berbigier, and T. L. Kelly* Synthesis of Conjugated Polymers: Comparing the Indophenine Reaction with Traditional Methods. ACS Applied Polymer Materials. 2024, 6, 8318-8325. https://doi.org/10.1021/acsapm.4c01169
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Citation
J. Faleiro Berbigier, and T. L. Kelly* Synthesis of Conjugated Polymers: Comparing the Indophenine Reaction with Traditional Methods. ACS Applied Polymer Materials. 2024, 6, 8318-8325. https://doi.org/10.1021/acsapm.4c01169
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DOI
10.1021/acsapm.4c01169