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Indophenine Reaction as a Method for Synthesizing Conjugated Polymers with Sub-1 eV Optical Bandgaps AITranslate

University of Saskatchewan; University of Saskatchewan; University of Saskatchewan; University of Saskatchewan
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Publisher: ACS
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Abstract AITranslate

Traditionally, conjugated polymer syntheses have relied heavily on metal-catalyzed cross-coupling reactions. These cross-couplings require appropriately functionalized monomers, increasing the length and complexity of the overall synthesis; in addition, some of the commonly used reagents (e.g., trialkyltin chlorides) are highly toxic. Even after a polymer has been successfully prepared, residual metal impurities can also compromise its optoelectronic properties and performance in devices. As such, there is a demand for metal-free approaches to conjugated polymer synthesis. In this work, the indophenine reaction was used to polymerize thiophene and bifunctional isatin comonomers, with only sulfuric acid used as the catalyst. The structural influence of the comonomers was evaluated using different thiophenes and bifunctional isatins. The resulting polymers have very wide absorption bands that span the UV/vis/NIR regions, with optical bandgaps as low as 0.76 eV. The polymers show electrochromic behavior, as determined through spectroelectrochemical measurements.

KeyWords AITranslate

organic semiconductor πconjugated polymer lowbandgap metalfree indophenine
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Basic Information:

DOI:https://doi.org/10.1021/acsapm.3c00978

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Citation Information:

Traditionally, conjugated polymer syntheses have relied heavily on metal-catalyzed cross-coupling reactions. These cross-couplings require appropriately functionalized monomers, increasing the length and complexity of the overall synthesis; in addition, some of the commonly used reagents (e.g., trialkyltin chlorides) are highly toxic. Even after a polymer has been successfully prepared, residual metal impurities can also compromise its optoelectronic properties and performance in devices. As such, there is a demand for metal-free approaches to conjugated polymer synthesis. In this work, the indophenine reaction was used to polymerize thiophene and bifunctional isatin comonomers, with only sulfuric acid used as the catalyst. The structural influence of the comonomers was evaluated using different thiophenes and bifunctional isatins. The resulting polymers have very wide absorption bands that span the UV/vis/NIR regions, with optical bandgaps as low as 0.76 eV. The polymers show electrochromic behavior, as determined through spectroelectrochemical measurements.

quote

GB/T 7714-2015 [1] Jônatas Faleiro Berbigier, Renita M. D’Souza, Raymond N. Bennett, et al. ACS Applied Polymer Materials, 2023(5). DOI:10.1021/acsapm.3c00978.
MLA [1] Jônatas Faleiro Berbigier, et al., ACS Applied Polymer Materials, no. 5, 2023, https://doi.org/10.1021/acsapm.3c00978.
APA [1] Jônatas Faleiro Berbigier, Renita M. D’Souza, Raymond N. Bennett, & Timothy L. Kelly. (2023). ACS Applied Polymer Materials(5). https://doi.org/10.1021/acsapm.3c00978
IEEE [1] Jônatas Faleiro Berbigier, Renita M. D’Souza, Raymond N. Bennett, and Timothy L. Kelly, ACS Applied Polymer Materials, no. 5, 2023, doi: 10.1021/acsapm.3c00978. keywords: {organic semiconductor;πconjugated polymer;lowbandgap;metalfree;indophenine}