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Open AccessArticle

Synthesis of Nixantphos Core-Functionalized Amphiphilic Nanoreactors and Application to Rhodium-Catalyzed Aqueous Biphasic 1-Octene Hydroformylation

1
CNRS, LCC (Laboratoire de Chimie de Coordination), Université de Toulouse, UPS, INPT, 205 route de Narbonne, BP 44099, F-31077 Toulouse CEDEX 4, France
2
Centre for Catalysis and Sustainable Chemistry, Department of Chemistry, Technical University of Denmark, Kemitorvet, Building 207, 2800 Kgs. Lyngby, Denmark
3
Institut Universitaire de France, 1 rue Descartes, 75231 Paris CEDEX 05, France
*
Authors to whom correspondence should be addressed.
Polymers 2020, 12(5), 1107; https://doi.org/10.3390/polym12051107
Received: 27 March 2020 / Revised: 24 April 2020 / Accepted: 8 May 2020 / Published: 12 May 2020
(This article belongs to the Special Issue Controlled Polymerization)
A latex of amphiphilic star polymer particles, functionalized in the hydrophobic core with nixantphos and containing P(MAA-co-PEOMA) linear chains in the hydrophilic shell (nixantphos-functionalized core-crosslinked micelles, or [email protected]), has been prepared in a one-pot three-step convergent synthesis using reversible addition-fragmentation chain transfer (RAFT) polymerization in water. The synthesis involves polymerization-induced self-assembly (PISA) in the second step and chain crosslinking with di(ethylene glycol) dimethacrylate (DEGDMA) in the final step. The core consists of a functionalized polystyrene, obtained by incorporation of a new nixantphos-functionalized styrene monomer (nixantphos-styrene), which is limited to 1 mol%. The nixantphos-styrene monomer was synthesized in one step by nucleophilic substitution of the chloride of 4-chloromethylstyrene by deprotonated nixantphos in DMF at 60 °C, without interference of either phosphine attack or self-induced styrene polymerization. The polymer particles, after loading with the [Rh(acac)(CO)2] precatalyst to yield [email protected], function as catalytic nanoreactors under aqueous biphasic conditions for the hydroformylation of 1-octene to yield n-nonanal selectively, with no significant amounts of the branched product 2-methyl-octanal. View Full-Text
Keywords: aqueous biphasic catalysis; hydroformylation; polymerization-induced self-assembly; RAFT polymerization; rhodium; nixantphos; water-confined polymeric nanoreactors aqueous biphasic catalysis; hydroformylation; polymerization-induced self-assembly; RAFT polymerization; rhodium; nixantphos; water-confined polymeric nanoreactors
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MDPI and ACS Style

Joumaa, A.; Gayet, F.; Garcia-Suarez, E.J.; Himmelstrup, J.; Riisager, A.; Poli, R.; Manoury, E. Synthesis of Nixantphos Core-Functionalized Amphiphilic Nanoreactors and Application to Rhodium-Catalyzed Aqueous Biphasic 1-Octene Hydroformylation. Polymers 2020, 12, 1107.

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