Direct and selective access to amino-poly(phenylene vinylenes)s with switchable properties by dimerizing polymerization of aminoaryl carbenes
SOBCZAK, Quentin
Institut des Sciences Moléculaires [ISM]
Laboratoire de Chimie des Polymères Organiques [LCPO]
Team 1 LCPO : Polymerization Catalyses & Engineering
Institut des Sciences Moléculaires [ISM]
Laboratoire de Chimie des Polymères Organiques [LCPO]
Team 1 LCPO : Polymerization Catalyses & Engineering
KUNCHE, Aravindu
Institut des Sciences Moléculaires [ISM]
Laboratoire de Chimie des Polymères Organiques [LCPO]
Team 1 LCPO : Polymerization Catalyses & Engineering
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Institut des Sciences Moléculaires [ISM]
Laboratoire de Chimie des Polymères Organiques [LCPO]
Team 1 LCPO : Polymerization Catalyses & Engineering
SOBCZAK, Quentin
Institut des Sciences Moléculaires [ISM]
Laboratoire de Chimie des Polymères Organiques [LCPO]
Team 1 LCPO : Polymerization Catalyses & Engineering
Institut des Sciences Moléculaires [ISM]
Laboratoire de Chimie des Polymères Organiques [LCPO]
Team 1 LCPO : Polymerization Catalyses & Engineering
KUNCHE, Aravindu
Institut des Sciences Moléculaires [ISM]
Laboratoire de Chimie des Polymères Organiques [LCPO]
Team 1 LCPO : Polymerization Catalyses & Engineering
Institut des Sciences Moléculaires [ISM]
Laboratoire de Chimie des Polymères Organiques [LCPO]
Team 1 LCPO : Polymerization Catalyses & Engineering
CARRIZO, Daiann Sosa
Institut des sciences analytiques et de physico-chimie pour l'environnement et les materiaux [IPREM]
Institut des sciences analytiques et de physico-chimie pour l'environnement et les materiaux [IPREM]
MIQUEU, Karinne
Institut des sciences analytiques et de physico-chimie pour l'environnement et les materiaux [IPREM]
Institut des sciences analytiques et de physico-chimie pour l'environnement et les materiaux [IPREM]
SOTIROPOULOS, Jean-Marc
Institut des sciences analytiques et de physico-chimie pour l'environnement et les materiaux [IPREM]
Institut des sciences analytiques et de physico-chimie pour l'environnement et les materiaux [IPREM]
CLOUTET, Eric
Laboratoire de Chimie des Polymères Organiques [LCPO]
Team 4 LCPO : Polymer Materials for Electronic, Energy, Information and Communication Technologies
Laboratoire de Chimie des Polymères Organiques [LCPO]
Team 4 LCPO : Polymer Materials for Electronic, Energy, Information and Communication Technologies
BROCHON, Cyril
Laboratoire de Chimie des Polymères Organiques [LCPO]
Team 4 LCPO : Polymer Materials for Electronic, Energy, Information and Communication Technologies
Laboratoire de Chimie des Polymères Organiques [LCPO]
Team 4 LCPO : Polymer Materials for Electronic, Energy, Information and Communication Technologies
TATON, Daniel
Laboratoire de Chimie des Polymères Organiques [LCPO]
Team 1 LCPO : Polymerization Catalyses & Engineering
Laboratoire de Chimie des Polymères Organiques [LCPO]
Team 1 LCPO : Polymerization Catalyses & Engineering
VIGNOLLE, Joan
Laboratoire de Chimie des Polymères Organiques [LCPO]
Team 1 LCPO : Polymerization Catalyses & Engineering
< Reduce
Laboratoire de Chimie des Polymères Organiques [LCPO]
Team 1 LCPO : Polymerization Catalyses & Engineering
Language
EN
Article de revue
This item was published in
Nature Communications. 2021-07-02, vol. 12, n° 1
English Abstract
AbstractDespite 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 ...Read more >
AbstractDespite 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.Read less <