

FOLLOWUS
State Key Laboratory of Supramolecular Structure and Materials, College of Chemistry, Jilin University, Changchun 130012, China
hjh2015@jlu.edu.cn (J.H.H.)
ytzhang2009@jlu.edu.cn (Y.T.Z.)
Received:14 December 2022,
Revised:2023-1-4,
Accepted:05 January 2023,
Online First:10 March 2023,
Published:01 November 2023
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Zhao, W. C.; Yuan, J.; He, J. H.; Zhang, Y. T. Controlled ring-opening (co)polymerization of renewable macrolactones by Al-based catalysts with different sidearms. Chinese J. Polym. Sci. 2023, 41, 1706–1713
Wu-Chao Zhao, Jing Yuan, Jiang-Hua He, et al. Controlled Ring-opening (Co)Polymerization of Renewable Macrolactones by Al-based Catalysts with Different Sidearms[J]. Chinese Journal of Polymer Science, 2023, 41(11): 1706-1713.
Zhao, W. C.; Yuan, J.; He, J. H.; Zhang, Y. T. Controlled ring-opening (co)polymerization of renewable macrolactones by Al-based catalysts with different sidearms. Chinese J. Polym. Sci. 2023, 41, 1706–1713 DOI: 10.1007/s10118-023-2947-x.
Wu-Chao Zhao, Jing Yuan, Jiang-Hua He, et al. Controlled Ring-opening (Co)Polymerization of Renewable Macrolactones by Al-based Catalysts with Different Sidearms[J]. Chinese Journal of Polymer Science, 2023, 41(11): 1706-1713. DOI: 10.1007/s10118-023-2947-x.
Four
Al
-based complexes with different sidearms were prepared and applied for controlled polymerization of pentadecalactone (PDL) furnishing polyesters with
M
w
high up to 90.3 kg/mol. Well-defined block copolyesters and random copolyesters with tailored
T
m
has also been obtained by copolymerizing PDL with small-lactones with controlling the polymerization condition.
It remains a challenging task to achieve ring-opening (co)polymerization (ROP) of macrolactones. Hence
we synthesized a series of
Al
-based catalysts and systemically investigated the effect of N-containing substituent on the sidearms on ROP of macrolactones.
Al3
possessing
N
-methyl group could effectively achieve controlled ROP of pentadecalactone (PDL) and macro(di)lactone ethylene brassylate (EB) in combination with BnOH
furnishing polyethylene-like PPDL and PEB with
M
w
up to 90.3 and 321 kg/mol
respectively. Random copolymerization of PDL and small-ring lactones
ε
-caprolactone (
ε
-CL) and
δ
-valerolactone (
δ
-VL) could prepare random copolyesters with tailored
T
m
in the range of 57−94 °C by controlling the ratios of PDL and
ε
-CL
δ
-VL. More importantly
well-defined block copolyesters could be obtained by sequential adding PDL and
ε
-CL
δ
-VL
which have been proved by GPC-MALLS
DSC and
13
C-NMR.
Ottou,W.N.;Sardon,H.;Mecerreyes,D.;Vignolle,J.;Taton,D.Updateandchallengesinorgano-mediatedpolymerizationreactions. Prog. Polym. Sci. 2016 , 56 ,64−115..
Zhang,X.;Fevre,M.;Jones,G.O.;Waymouth,R.M.Catalysisasanenablingscienceforsustainablepolymers. Chem. Rev. 2018 , 118 ,839−885..
Fortman,D.J.;Brutman,J.P.;De,H.;G.X.;Snyder,R.L.;Dichtel,W.R.;Hillmyer,M.A.Approachestosustainableandcontinuallyrecyclablecross-linkedpolymers. ACS Sustainable Chem. Eng. 2018 , 6 ,11145−11159..
Labet,M.;Thielemans,W.Synthesisofpolycaprolactone:areview. Chem. Soc. Rev. 2009 , 38 ,3484−3504..
Cabaret,D.O.;Vaca,M.B.;Bourissou,D.Controlledring-openingpolymerizationoflactideandglycolide. Chem. Rev. 2004 , 104 ,6147−6176..
Hillmyer,M.A.;Tolman,W.B.Aliphaticpolyesterblockpolymers:renewable,degradable,andsustainable. Acc. Chem. Res. 2014 , 47 ,2390−2396..
Li,Y.;Rodrigues,J.;Tomas,H.Injectableandbiodegradablehydrogels:gelation,biodegradationandbiomedicalapplications. Chem. Soc. Rev. 2012 , 41 ,2193−2221..
Jerome,C.;Lecomte,P.Recentadvancesinthesynthesisofaliphaticpolyestersbyring-openingpolymerization. Adv. Drug. Deliv. Rev. 2008 , 60 ,1056−1076..
Kamber,N.E.;Jeong,W.;Waymouth,R.M.;Pratt,R.C.;Lohmeijer,B.G.G.;Hedrick,J.L.Organocatalyticring-openingpolymerization. Chem. Rev. 2007 , 107 ,5813−5840..
Stirling,E.;Champouret,Y.;Visseaux,M.Catalyticmetal-basedsystemsforcontrolledstatisticalcopolymerisationoflactidewithalactone. Polym. Chem. 2018 , 9 ,2517−2531..
Hong,M.;Chen,E.Y.Towardstrulysustainablepolymers:ametal-freerecyclablepolyesterfrombiorenewablenon-strained γ -butyrolactone. Angew. Chem. Int. Ed. 2016 , 55 ,4188−4193..
Alamri,H.;Zhao,J.P.;Pahovnik,D.;Hadjichristidis,N.Phosphazene-catalyzedring-openingpolymerizationof ε -caprolactone:influenceofsolventsandinitiators. Polym. Chem. 2014 , 5 ,5471−5478..
Wang,Q.Y.;Zhao,W.C.;He.J.H.;Zhang,Y.T.;Chen,E.Y.Livingring-openingpolymerizationoflactonesby N -heterocyclicolefin/Al(C 6 F 5 ) 3 Lewispairs:structuresofintermediates,kinetics,andmechanism. Macromolecules 2017 , 50 ,123−136..
Pothupitiya,J.U.;Dharmaratne,N.U.;Jouaneh,T.M.M.;Fastnacht,K.V.;Coderre,D.N.;Kiesewetter,M.K.H-bondingorganocatalystsfortheliving,solvent-freering-openingpolymerizationoflactones:towardanall-lactones,all-conditionsapproach. Macromolecules 2017 , 50 ,8948−8954..
Arbaoui,A.;Redshaw,C.Metalcatalystsfor ε -caprolactonepolymerization. Polym. Chem. 2010 , 1 ,801−826..
Zhao,W.C.;Wang,Q.Y.;CuiY.P.;He,J.H.;ZhangY.T.Living/controlledring-opening(co)polymerizationoflactonesbyAl-basedcatalystswithdifferentsidearms. Dalton Trans. 2019 , 48 ,7167−7178..
Chen,C.T.;Huang,C.A.;HuangB.H.Aluminumcomplexessupportedbytridentateaminophenoxideligandasefficientcatalystsforring-openingpolymerizationof ε -caprolactone. Macromolecules 2004 , 37 ,7968−7973..
Osten,K.M.;Mehrkhodavandi,P.Indiumcatalystsforringopeningpolymerization:exploringtheimportanceofcatalystaggregation. Acc. Chem. Res. 2017 , 50 ,2861−2869..
Wei,Y.;Wang,S.;Zhou,S.Aluminiumalkylcomplexes:synthesis,structure,andapplicationinROPofcyclicesters. Dalton Trans. 2016 , 45 ,4471−4485..
Kan,C.;Hu,J.W.;Huang,Y.;Wang,H.B.;Ma,H.Y.Highlyisoselectiveandactivezinccatalystsforrac-lactidepolymerization:effectofpendantgroupsofaminophenolateligands. Macromolecules 2017 , 50 ,7911−7919..
Li,M.;Chen,M.;Chen,C.L.Ring-openingpolymerizationofrac-lactideusinganilinotropone-basedaluminiumcomplexes-sidearmeffectonthecatalysis. Polymer 2015 , 64 ,234−239..
Yang,W.X.;Zhao,K.Q.;Prior,T.J.;Hughes,D.L.;Arrbaoui,A.;Elsegood,M.R.J.;Redshaw,C.StructuralstudiesofSchiff-base[2+2]macrocyclesderivedfrom2,2’-oxydianilineandtheROPcapabilityoftheirorganoaluminiumcomplexes. Dalton Trans. 2016 , 45 ,11990−12005..
Kong,W.L.;Chai,Z.Y.;Wang,Z.X.SynthesisofN,N,O-chelatezincandaluminumcomplexesandtheircatalysisinthering-openingpolymerizationof ε -caprolactoneandrac-lactide. Dalton Trans. 2014 , 43 ,14470−14480..
Gazzano,M.;Malta,V.Focarete,M.L.;Scandola,M.;Gross,R.A.Crystalstructureofpoly( ω -pentadecalactone). J. Polym. Sci., B: Polym. Phys. 2002 , 41 ,1009−1013..
Skoglund,P.;Fransson.A.Thermophysicalpropertiesofpolypentadecanolactone. Polymer 1998 , 39 ,1899−1906..
Wilison,J.A.;Hopkins,S.A.;Wright,P.M.;Dove,A.P.Synthesisandpostpolymerizationmodificationofone-pot ω -pentadecalactoneblock-likecopolymers. Biomacromolecules 2015 , 16 ,3191−3200..
Myers,D.;Witt,T.;Cyriac,A.;Bown,M.;Mecking,S.;Williams,C.K.Ringopeningpolymerizationofmacrolactones:highconversionsandactivitiesusinganyttriumcatalyst. Polym. Chem. 2017 , 8 ,5780−5785..
Geus,D.M.;Meulen,I.V.D;Goderis,B.;Hecke,V.K.;Dorschu,M.;Werff,H.V.D.;Koning,C.E.;Heise,A.Performancepolymersfromrenewablemonomers:highmolecularweightpoly(pentadecalactone)forfiberapplications. Polym. Chem. 2010 , 1 ,525−533..
Li,C.C.;Pan,S.J.;Xu,W.J.;Lu,Y.B.;Wang,P.P.;Zhang,F.M.;Gross,R.A.Lipase-catalyzedring-openingcopolymerizationof ω -pentadecalactoneand δ -valerolactonebyreactiveextrusion. Green Chem. 2020 , 22 ,662−668..
Focarete,M.L.;Scandola,M.;Kumar,A.;Gross,R.A.Physicalcharacterizationofpoly( ω -pentadecalactone)synthesizedbylipase-catalyzedring-openingpolymerization. J. Polym. Sci., Part B: Polym. Phys. 2001 , 39 ,1721..
Meulen,D.V.I.;Geus,M.D.;Antheunis,H.;Deumens,R.;Joosten,E.A.J.;Koning,C.E.;Heise,A.Polymersfromfunctionalmacrolactonesaspotentialbiomaterials:enzymaticringopeningpolymerization,biodegradation,andbiocompatibility. Biomacromolecules 2008 , 9 ,3404−3410..
Mee,L.V.D;Helmich,F.;Bruijn,D.R.;Vekemans,J.A.J.M.;Palmans,A.R.A.;Meijer,E.W.Investigationoflipase-catalyzedring-openingpolymerizationsoflactoneswithvariousringsizes:kineticevaluation. Macromolecules 2006 , 39 ,5021−5027..
Bouyahyi,M.;Pepels,M.P.F.;Heise,A.;Duchateau,R. ω -Pentandecalactonepolymerizationand ω -pentadecalactone/ ε -caprolactonecopolymerizationreactionsusingorganiccatalysts. Macromolecules 2012 , 45 ,3356−3366..
Ladelta,V.;Bilalis,P.;Gnanou,Y.;Hadjichristidis,N.Ring-openingpolymerizationof ω -pentadecalactonecatalyzedbyphosphazenesuperbases. Polym. Chem. 2017 , 8 ,511−515..
Naumann,S.;Scholten,P.B.;Wilson,J.A.;Dove.A.P.Dualcatalysisforselectivering-openingpolymerizationoflactones:evolutiontowardsimplicity. J. Am. Chem. Soc. 2015 , 137 ,14439−14445..
Walther,P.;Naumann,S. N -heterocyclicolefin-based(co)polymerizationofachallengingmonomer:homopolymerizationof ω -pentadecalactoneanditscopolymerswith γ -butyrolactone, δ -valerolactone,and ε -caprolactone. Macromolecules 2017 , 50 ,8406−8416..
Wang,B.;Pan,L.;Ma,Z.;Li,Y.Ring-openingpolymerizationwithLewispairsandsubsequentnucleophilicsubstitution:apromisingstrategytowell-definedpolyethylene-likepolyesterswithouttransesterification. Macromolecules. 2018 , 51 ,836−845..
Bouyahyi,M.;Duchateau,R.Metal-basedcatalystsforcontrolledring-openingpolymerizationofmacrolactones:highmolecularweightandwell-definedcopolymerarchitectures. Macromolecules 2014 , 47 ,517−524..
Huang,H.C.;Wang,B.Chen,X.L.;Pan,L.;Li,Y.S.Ring-openingpolymerizationof(macro)lactonesbyhighlyactivemononuclearsalen–aluminumcomplexesbearingcyclic β -ketoiminatoligand. J. Polym. Sci., Part A: Polym. Chem. 2019 , 57 ,973−981..
Pepels,M.P.F.;Bouyahyi,M.;Heise,A.;Duchateau,R.Kineticinvestigationonthecatalyticring-opening(co)polymerizationof(macro)lactonesusingaluminumsalencatalysts. Macromolecules 2013 , 46 ,4324−4334..
Meulen,V.D.;Gubbels,E.;Huijser,S.;Sablong.R.;Koning,C.E.;Heise,A.Catalyticring-openingpolymerizationofrenewablemacrolactonestohighmolecularweightpolyethylene-likepolymers. Macromolecules 2011 , 44 ,4301−4305..
Roymuhury,S.K.;Chakraborty,D.;Ramkumar,V.Aluminiumcomplexesbearing N , O -aminophenolligandsasefficientcatalystsfortheringopeningpolymerizationoflactide. Eur. Polym. J. 2015 , 70 ,203−214..
Williams,C.K.;Breyfogle,L.E.;Choi,S.K.;Nam,W.;G,V.;Young,J.;Hillmyer,M.A.;Tolman,W.B.Ahighlyactivezinccatalystforthecontrolledpolymerizationoflactide. J. Am. Chem. Soc. 2003 , 125 ,11350−11359..
Cameron,P.A.;Gibson,V.C.;Redshaw,C.;Segal,J.A.;White,A.J.P.;Williams,D.J.SynthesisandcharacterisationofneutralandcationicalkylaluminiumcomplexesbearingN,O-Schiffbasechelateswithpendantdonorarms. J. Chem. Soc., Dalton Trans. 2002 ,415−422..
Kumar,A.;Kalra,B.;Dekhterman,A.;Gross,R.A.Efficientring-openingpolymerizationandcopolymerizationof ε -caprolactoneand ω -pentadecalactonecatalyzedby Candida Antartica lipaseB. Macromolecules 2000 , 33 ,6303−6309..
Kamiya,N.;Sakurai,M.;Inoue,Y.;Chujo,R.Isomorphicbehaviorofrandomcopolymers:thermodynamicanalysisofcocrystallizationofpoly(3-hydroxybutyrate- co -3-hydroxyvalerate). Macromolecules 1991 , 24 ,3888−3892..
Ceccorulli,G.;Scandola,M.;Kumar,A.;Kalra,B.;Gross,R.A.Cocrystallizationofrandomcopolymersof ω -pentadecalactoneand ε -caprolactonesynthesizedbylipasecatalysis. Biomacromolecules 2005 , 6 ,902−907..
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