Synthesis and electrochromic properties of polyamines containing a 4,4′-diaminotriphenylamine- N , N ′-diyl unit in the polymer backbone: Ru-catalyzed N–H insertion polycondensation of 1,4-phenylenebis(diazoacetate) with 4,4′-diaminotriphenylamine derivatives

A new type of polyamine containing a 4,4′-diaminotriphenylamine- N , N ′-diyl unit in the main chain was prepared by Ru-catalyzed polycondensation of a bis(diazocarbonyl) compound with 4,4′-diaminotriphenylamine, where the propagation is N–H insertion of a carbene–carbon atom generated from the diaz...

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Veröffentlicht in:Polymer chemistry 2022-11, Vol.13 (46), p.6369-6376
Hauptverfasser: Wang, Yun-Chi, Shao, Yu-Jen, Liou, Guey-Sheng, Nagao, Sota, Makino, Yusuke, Akiyama, Eita, Kato, Masaaki, Shimomoto, Hiroaki, Ihara, Eiji
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container_end_page 6376
container_issue 46
container_start_page 6369
container_title Polymer chemistry
container_volume 13
creator Wang, Yun-Chi
Shao, Yu-Jen
Liou, Guey-Sheng
Nagao, Sota
Makino, Yusuke
Akiyama, Eita
Kato, Masaaki
Shimomoto, Hiroaki
Ihara, Eiji
description A new type of polyamine containing a 4,4′-diaminotriphenylamine- N , N ′-diyl unit in the main chain was prepared by Ru-catalyzed polycondensation of a bis(diazocarbonyl) compound with 4,4′-diaminotriphenylamine, where the propagation is N–H insertion of a carbene–carbon atom generated from the diazocarbonyl group of the former monomer with N 2 elimination. In the well-defined polyamines newly prepared in this study, the two primary amino groups in the diamine monomer remain as secondary amino groups in the polymer main chain, in contrast to the previously reported polymers prepared by polycondensation of the same diamine monomers, where the amino groups were incorporated into an amide or imide linkage. The resulting triphenyl amino framework in the polymer main chain possesses three amino groups, each of which can independently participate in the electrochemical process as a redox center with applied electrochemical potentials. The electrochromic properties of thin films and electrochromic devices of the polyamines were evaluated with cyclic voltammetry and spectroelectrochemistry, revealing that the polyamines indeed underwent an expected three-stage redox process.
doi_str_mv 10.1039/D2PY01118B
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subjects Chains (polymeric)
Diamines
Electrochromic cells
Electrochromism
Insertion
Monomers
Polyamines
Polymer chemistry
Polymers
Thin films
title Synthesis and electrochromic properties of polyamines containing a 4,4′-diaminotriphenylamine- N , N ′-diyl unit in the polymer backbone: Ru-catalyzed N–H insertion polycondensation of 1,4-phenylenebis(diazoacetate) with 4,4′-diaminotriphenylamine derivatives
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