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1. Synthesis of natural rubber-based telechelic cis-1,4-polyisoprenes and their use to prepare block copolymers via RAFT polymerization

Author

Jean‐Claude Soutif, Nitinart Saetung, Irène Campistron, Jean Francois Pilard, Sagrario Pascual, Laurent Fontaine, Unité de chimie organique moléculaire et macromoléculaire (UCO2M), and Le Mans Université (UM)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)

Subjects
Polymers and Plastics, Radical polymerization, General Physics and Astronomy, 02 engineering and technology, 010402 general chemistry, 01 natural sciences, Reductive amination, polyisoprene reversible addition fragmentation chaintransfer (RAFT), Polymer chemistry, Materials Chemistry, Copolymer, Reversible addition−fragmentation chain-transfer polymerization, ComputingMilieux_MISCELLANEOUS, Telechelic polymer, Chemistry, Organic Chemistry, Chain transfer, oxidative degradation, 021001 nanoscience & nanotechnology, 0104 chemical sciences, End-group, [CHIM.POLY]Chemical Sciences/Polymers, telechelics, Polymerization, 0210 nano-technology, naturel rubber
Abstract

A new trithiocarbonate functionalized cis-1,4-polyisoprene was obtained from oxidative degradation of natural rubber followed by reductive amination and amidation. The structure of the resulting functionalized cis-1,4-polyisoprene was confirmed by a combination of 1H NMR spectroscopy, 13C NMR spectroscopy, MALDI-TOF mass spectrometry and FTIR spectroscopy. 1H NMR spectroscopy showed that the trithiocarbonate functionality was equal to one. The well-defined trithiocarbonyl-end functionalized cis-1,4-polyisoprene was used as a macromolecular chain transfer agent (macroCTA) to mediate the RAFT polymerization of t-BA using AIBN as the initiator ([t-BA]0/[macroCTA]0/[AIBN]0 = 250/1/0.2) in toluene at 60 °C. The resulting PI-b-P(t-BA) diblock copolymer presents an unimodal SEC trace shifted toward higher molecular weight in comparison with the SEC trace of the macroCTA, indicating that the polymerization of the second block is effective. The characteristics of the copolymer were determined by SEC ( M ¯ n = 26,000 g mol−1, PDI = 1.76) and 1H NMR spectroscopy ( DP ¯ n (PI) = 62 and DP ¯ n (P(t-BA)) = 87).

Published
2011
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2. Synthesis of Functionalized 1-cyclooctyl-3-methyl-1,2,3-triazolium via click chemistry and their polymerization by ROMP

Author

Loubna Najemi, Jean François Pilard, and Mohammed Berrada

Subjects
Ionic liquids, Poly(1,2,3-triazolium)s, click chemistry, ROMP, Chemistry, QD1-999
Abstract

This paper describes the synthesis of a new ionic liquid (IL) monomer of 5-substituted cyclooctene 1,2,3-triazolium iodides salt via click chemistry, and an anion exchange reaction with two different counteranions: bis(trifluoromethylsulfonyl)imide [N(SO2CF3)2]−(NTf2−), and hexafluorophosphate ([PF6]−). The structural properties of all monomers were determined by MALDI-TOF-MS, (1H; 13C; 19F;)NMR spectroscopy. 1,2,3-triazolium-based poly(ionic liquid)s (TPILs) with the pendant triazolium moieties were also synthesized by Ring-Opening Metathesis Polymerization (ROMP) using Grubbs second generation (Grubbs II) ruthenium as a catalyst with good control during the polymerization process and gave viscous solutions. The Synthesis of the polymers (TPILs) was confirmed by 1HNMR spectroscopy. The thermal properties were characterized by thermogravimetric analysis (TGA), and differential scanning calorimetry (DSC). The thermal stability of monomers was found to be high (∼286°C). Furthermore, monomers salts with [NTf2−] have low melting points below 100°C (25-99°C), and their TPILs are viscous liquids at room temperature, with a low glass transition temperature (Tg = -23°C). This result suggests that the 5-substituted cyclooctene 1,2,3-triazolium ionic liquid monomer offers high chain flexibility to the resulting polymers (TPILs). Hence this new class of IL monomer and TPILs may be potentially useful in electrolyte membrane applications.

Published
2022
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3. Synthesis of 3,6-Divinyl-1,2,4,5-Tetrazine, the First Member of the Elusive Vinyltetrazine Family

Author

Lionel Beller, Eric Pasquinet, Jean Francois Pilard, Stephanie Pican, Didier Poullain, Vincent Lapinte, Laurent Fontaine, Unité de chimie organique moléculaire et macromoléculaire (UCO2M), Le Mans Université (UM)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC), Institut Charles Gerhardt Montpellier - Institut de Chimie Moléculaire et des Matériaux de Montpellier (ICGM ICMMM), Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM)-Centre National de la Recherche Scientifique (CNRS)-Université de Montpellier (UM)-Université Montpellier 1 (UM1)-Université Montpellier 2 - Sciences et Techniques (UM2)-Institut de Chimie du CNRS (INC), CEA Le Ripault (CEA Le Ripault), Direction des Applications Militaires (DAM), Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Commissariat à l'énergie atomique et aux énergies alternatives (CEA), Le Mans Université (UM)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), and Université Montpellier 1 (UM1)-Université Montpellier 2 - Sciences et Techniques (UM2)-Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)

Subjects
heterocycles, azo compounds, 010405 organic chemistry, Organic Chemistry, Condensation, cyclizations, fused ring systems, 010402 general chemistry, 01 natural sciences, 3. Good health, 0104 chemical sciences, chemistry.chemical_compound, Tetrazine, condensation, [CHIM.POLY]Chemical Sciences/Polymers, chemistry, Polymer chemistry, Derivative (chemistry)
Abstract

International audience; The synthesis of the first vinyltetrazine derivative is ­described. 3,6-Divinyl-1,2,4,5-tetrazine was obtained following a methodology involving cyclization from an imidate and use of 2-phenylsulfonylethyl groups as masked vinyl entities. The first properties of this unique compound are reported.

Published
2009
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