Opportunities for organocatalysis in polymer synthesis via step-growth methods. (March 2019)

• Record Type: Journal Article
• Authors: Bossion, Amaury; Heifferon, Katherine V.; Meabe, Leire; Zivic, Nicolas; Taton, Daniel; Hedrick, James L.; Long, Timothy E.; Sardon, Haritz
• Is Part Of: Progress in polymer science. Volume 90(2019)
• Page Start: 164
• Page End: 210
• Publication Date: 2019-03
• Subjects: AcOH acetic acid -- ADMET α, ω-dienemetathesis polymerization -- AMP Acetal Metathesis Polymerization -- BAIL Brønsted acid ionic liquid -- [BBSIm]Tf2N 4-(3′-butyl-1′-imidazolio)-1-butanesulfonic acid bis(trifluoromethylsulfonyl)imidide -- BDMAEE 2, 2′-bis-(dimethylaminoethyl ether) -- BF3OEt2 boron trifluoride diethyl ether complex -- BHET bis(2-hydroxyethyl)terephtalate -- bis-MPA 2, 2-bis(hydroxymethyl)-propionic acid -- bis-MPA-TEMPO 4-hydroxy-2, 2, 6, 6-tetramethylpiperidine 1-oxyl 3-hydroxy-2-(hydroxymethyl)-2-methylpropanoate -- BEMP 2-tert-butylimino-2-diethylamino-1, 3-dimethylperhydro-1, 3, 2-diazaphosphorine -- CSA camphor-10-sulfonic acid -- Đ dispersity -- DABCO 1, 4-diazabicyclo [2, 2, 2]octane -- DBN 1, 5-diazabicyclo[4.3.0]non-5-ene -- DBSA dodecylbenzenesulfonic acid -- DBTDL dibutyltin dilaurate -- DBU 1, 8-diazabicyclo[5.4.0]undec-7-ene -- DCM dichloromethane -- DES diethylstilbestrol -- DFT density functional theory -- DOX doxorubicin -- DMAP 4-dimethylaminopyridine -- DMC dimethyl carbonate -- DMF N, N-dimethylformamide -- DMSO dimethyl sulfoxide -- DMT dimethyl terephthalate -- DPC diphenyl carbonate -- DPP diphenyl phosphate -- EG ethylene glycol -- Et-MDEA N, N-bis(2-hydroxyethyl)-N-methylbutan-1-aminium bromide -- Hex-MDEA N, N-bis(2-hydroxyethyl)-N-methylhexan-1-aminium bromide -- HCl hydrochloric acid -- HMDI hexamethylene diisocyanate -- H3PO4 phosphoric acid -- H2SO4 sulfuric acid -- IPDI isophorone diisocyanate -- KHMDS potassium bis-(trimethylsilyl)amide -- KOMe potassium methoxide -- KO-t-Bu potassium tert-butoxide -- LCST lower critical solution temperature -- MDA 4, 4′-diaminodiphenylmethane -- MDEA N-methyldiethanolamine -- MeCN acetonitrile -- MeOTF trifluoromethanesulfonate -- Mn number-average molar mass -- MRI magnetic resonance imaging -- MSA methanesulfonic acid -- MTBD N-methyl 7-methyl-1, 5, 7-triazabicyclo[4.4.0]dec-5-ene -- Mw weight-average molar mass -- Nf2NH bis(1, 1, 2, 2, 3, 3, 4, 4, 4-nonafluoro-1-butanesulfonyl)imide -- NfOH 1, 1, 2, 2, 3, 3, 4, 4, 4-nonafluoro-1-butanesulfonic acid -- NHC N-heterocyclic carbene -- NHC-CO2 azolium-2-carboxylate -- NIPU non-isocyanate polyurethane -- NMP N-methyl-2-pyrrolidone -- [OBSIm]Tf2N 4-(3′-octyl-1′-imidazolio)-1-butane-sulfonic acid bis(trifluoromethylsulfonyl) imidide -- P2-Et 1-Ethyl-2, 2, 4, 4, 4-pentakis(dimethylamino)-2λ5, 4λ5-catenadi(phosphazene) -- PCS pyridinium camphorsulfonate -- PEG polyethylene glycol -- PEO polyethylene oxide -- PET poly(ethyleneterephtalate) -- Ph3P triphenylphosphine -- PHU poly(hydroxyurethane) -- PHUU poly(hydroxyurea−urethane) -- PPV poly(1, 4-phenylenevinylene) -- PPY 4-pyrrolidinopyridine -- PTMO poly(tetramethylene oxide) -- PTSA p-toluene sulfonic acid -- PTSAA p-toluene sulfonic anhydride -- PTS pyridinium p-toluenesulfonate -- p-TsOH p-toluene sulfonic acid monohydrate -- PU polyurethane -- PVA polyvinyl alcohol -- REMP ring expansion metathesis polymerization -- ROIP ring opening insertion metathesis polymerization -- ROP ring-opening poylmerization -- RT room temperature (23 ± 5°C) -- SP (+)-sparteine -- TBD 1, 5, 7-triazabicyclo[4.4.0]dec-5-ene -- t-BuP1 tert-butylimino-tris(dimethylamino)phosphorene -- t-BuP2 1-tert-Butyl-2, 2, 4, 4, 4-pentakis(dimethylamino)-2λ5, 4λ5-catenadi(phosphazene) -- t-BuP4 1-tert-butyl-4, 4, 4-tris(dimethylamino)-2, 2-bis[tris(dimethylamino)-phosphoranylidenamino]-2λ5, 4λ5-catenadi(phosphazene) -- TEA triethylamine -- TFA trifluoroacetic acid -- Tf2NH bis(trifluoromethanesulfonyl)imide -- TfOH triflic acid -- THF tetrahydrofuran -- Ti(OBu)4 titanium(IV) butoxide -- TMC trimethylene carbonate -- TMG 1, 1, 3, 3-tetramethylguanidine -- TMS trimethylsilyl -- TU thiourea; Organocatalysis -- Step-growth polymerization -- Organic acids -- Organic bases -- Dual catalysts; Polymers -- Periodicals; Polymerization -- Periodicals; Polymers -- Industrial applications -- Periodicals; Polymères -- Périodiques; Polymérisation -- Périodiques; 547.7
• DOI: 10.1016/j.progpolymsci.2018.11.003
• Languages: English
• ISSNs: 0079-6700

Abstract

Graphical abstract: Abstract: Organocatalysis has emerged as an invaluable tool for polymer synthesis and has already demonstrated versatility for replacing organometallic catalysts in many polymerization reactions. The overall ease of removal and lower toxicity of organocatalysts relative to their common metal counterparts has also nurtured development especially in chain growth polymerizations to achieve precision macromolecular architectures for application in the biomedical space. The application of organocatalysts in step-growth polymerizations of polymers, including polyesters, polycarbonates, and polyurethanes, has garnered fewer studies in spite of the large array of benefits that could be achieved. Step-growth polymers account for nearly 20 wt. % of the Word Plastic Production and play a vital role in many technologies as engineering plastics and high performance polymeric materials with outstanding thermomechanical performance. Step-growth polymerizations are achieved using monomers with a diversity of chemical functionality. Consequently, a vast array of polymeric structures are attainable and will impact diverse applications in energy, aerospace, medicine, transportation, and construction. This review article will highlight the recent advances in organocatalysis in step growth polymerizations. We will primarily focus our review on the synthesis of commercially important polyesters and polyurethanes using organocatalysis, however, the review will also emphasize recent literature describing less explored polymers, such as polyethers, polycarbonates, and polybenzoins, which have recently employed organocatalysts. Moreover, the article will draw attention to recent efforts in the use of carbon dioxide as a monomer for the preparation of step-growth polymers in the presence of organocatalysis.