Direct and selective access to amino-poly(phenylene vinylenes)s with switchable properties by dimerizing polymerization of aminoaryl carbenes

Quentin Sobczak, Aravindu Kunche, Damien Magis, Daiann Sosa Carrizo, Karinne Miqueu, Jean-Marc Sotiropoulos, Eric Cloutet, Cyril Brochon, Yannick Landais, Daniel Taton () and Joan Vignolle ()
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Quentin Sobczak: Laboratoire de Chimie des Polymères Organiques, CNRS, Université de Bordeaux IPB-ENSCPB
Aravindu Kunche: Laboratoire de Chimie des Polymères Organiques, CNRS, Université de Bordeaux IPB-ENSCPB
Damien Magis: Université de Bordeaux, ISM, UMR 5255, 33400 Talence, France - CNRS, ISM, UMR 5255
Daiann Sosa Carrizo: CNRS, Université de Pau & Pays de l’Adour E2S UPPA, IPREM UMR 5254, Hélioparc.
Karinne Miqueu: CNRS, Université de Pau & Pays de l’Adour E2S UPPA, IPREM UMR 5254, Hélioparc.
Jean-Marc Sotiropoulos: CNRS, Université de Pau & Pays de l’Adour E2S UPPA, IPREM UMR 5254, Hélioparc.
Eric Cloutet: Laboratoire de Chimie des Polymères Organiques, CNRS, Université de Bordeaux IPB-ENSCPB
Cyril Brochon: Laboratoire de Chimie des Polymères Organiques, CNRS, Université de Bordeaux IPB-ENSCPB
Yannick Landais: Université de Bordeaux, ISM, UMR 5255, 33400 Talence, France - CNRS, ISM, UMR 5255
Daniel Taton: Laboratoire de Chimie des Polymères Organiques, CNRS, Université de Bordeaux IPB-ENSCPB
Joan Vignolle: Laboratoire de Chimie des Polymères Organiques, CNRS, Université de Bordeaux IPB-ENSCPB

Nature Communications, 2021, vol. 12, issue 1, 1-8

Abstract: Abstract Despite the ubiquity of singlet carbenes in chemistry, their utility as true monomeric building blocks for the synthesis of functional organic polymers has been underexplored. In this work, we exploit the capability of purposely designed mono- and bis-acyclic amino(aryl)carbenes to selectively dimerize as a general strategy to access diaminoalkenes and hitherto unknown amino-containing poly(p-phenylene vinylene)s (N-PPV’s). The unique selectivity of the dimerization of singlet amino(aryl)carbenes, relative to putative C-H insertion pathways, is rationalized by DFT calculations. Of particular interest, unlike classical PPV’s, the presence of amino groups in α-position of C=C double bonds in N-PPV’s allows their physico-chemical properties to be manipulated in different ways by a simple protonation reaction. Hence, depending on the nature of the amino group (iPr2N vs. piperidine), either a complete loss of conjugation or a blue-shift of the maximum of absorption is observed, as a result of the protonation at different sites (nitrogen vs. carbon). Overall, this study highlights that singlet bis-amino(aryl)carbenes hold great promise to access functional polymeric materials with switchable properties, through a proper selection of their substitution pattern.

Date: 2021
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DOI: 10.1038/s41467-021-24274-7

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