高分子立构复合体的研究进展
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摘要
高分子立构复合体是高分子异构体之间通过协同性的立构选择相互作用力形成的一类特殊的高分子晶体。高分子立构复合体与其均聚物晶体相比有着更为优异的性能,例如更高的熔点,更好的结晶性(结晶速度快,结晶度高)等,这些独特的特性在学术上和工业应用上都吸引了研究者的关注。本工作归纳总结了常见立构复合体以及新近合成的立构复合体的形成机理以及结构特点,对其在材料加工领域以及生物医药领域的应用进行了简单的介绍,并对高分子立构复合体今后的发展进行了展望。
Polymer stereocomplex is a kind of unique polymer crystal driven by stereoselective interaction which is formed between segments having different stereochemical configuration.Compared with the homo-crystal,stereocomplex has a higher melting point and higher crystallization capacity(crystalline rate,crystalline degree etc.).These unique properties attract the attention of researchers from both academic and industrial field.In this review,a comprehensive introduction on the formation mechanism and structure character of several typical polymer stereocomplexes was given.Then the application of polymer stereocomplex in material science and bioscience fields were also introduced briefly.
Polymer stereocomplex is a kind of unique polymer crystal driven by stereoselective interaction which is formed between segments having different stereochemical configuration.Compared with the homo-crystal,stereocomplex has a higher melting point and higher crystallization capacity(crystalline rate,crystalline degree etc.).These unique properties attract the attention of researchers from both academic and industrial field.In this review,a comprehensive introduction on the formation mechanism and structure character of several typical polymer stereocomplexes was given.Then the application of polymer stereocomplex in material science and bioscience fields were also introduced briefly.
引文
[1]PAULING L,COREY R B.Two rippled-sheet configurations of polypeptide chains,and a note about the pleated sheets[J].Proceedings of the National Academy of Sciences,1953,39(4):253-256.
[2]FOX T G,GARRETT B S,GOODE W E,et al.Crystalline polymers of methylmethacrylate[J].Journal of the American Chemical Society,1958,80(7):1768-1769.
[3]LOHMEYER J H G M,TAN Y Y,LAKO P,et al.Stereoselective association between isotactic poly(methylmethacrylate)and syndiotactic poly(methacrylic acid)[J].Polymer,1978,19(10):1171-1175.
[4]BOSSCHER F,KEEKSTRA D,CCHALLA G.The influence of ester groups on the stereocomplex formation between different polyalkylmethacrylates[J].Polymer,1981,22(1):124-126.
[5]LONGO J M,DICICCIO A M,COATES G W.Poly(propylene succinate):A new polymer stereocomplex[J].Journal of the American Chemical Society,2014,136(45):15897-15900.
[6]LIU Y,REN W M,WANG M,et al.Crystalline stereocomplexed polycarbonates:Hydrogen-bond-driven interlocked orderly assembly of the opposite enantiomers[J].Angewandte Chemie International Edition,2015,54(7):2241-2244.
[7]AURIEMMA F,ROSA C D,ROSARIA M,et al.Stereocomplexed poly(limonene carbonate):A unique example of the cocrystallization of amorphous enantiomeric polymers[J].Angewandte Chemie International Edition,2014,54(4):1215-1218.
[8]TSUJI H.Poly(lactide)stereocomplexes:Formation,structure,properties,degradation,and applications[J].Macromolecular Bioscience,2007,5(7):569-597.
[9]TSUBOI M,WADA A,NAGASHIMA N.Sidechainsidechain interaction between the alpha-helices of L-and Dpolypeptide chains[J].Journal of Molecular Biology,1961,3:705-706.
[10]YOSHIDA T,SAKURAI S,OKUDA T,et al.A racemic compound ofα-helical polypeptide[J].Journal of the American Chemical Society,2002,84(18):3590-3591.
[11]DUMAS P,SPASSKY N,SIGWAL P.Preparation and polymerization of racemic and optically active tert-butyl thiirane[J].Die Makromolekulare Chemie,1972,156(1):55-64.
[12]SAKAKIHARA H,TAKAHASHI Y,TADOKORO H,et al.Structural studies of isotactic poly(tert-butylethylene oxide)[J].Macromolecules,1973,6(2):205-212.
[13]GRENIER D,PRUD H R E.Complex formation between enantiomeric polyesters[J].Journal of Polymer Science Polymer Physics Edition,1984,22(4):577-587.
[14]IKADA Y,JAMSHIDI K,TSUJI H,et al.Stereocomplex formation between enantiomeric poly(lactides)[J].Macromolecules,1987,20(4):904-906.
[15]VOYER R,PRUD H R E.Stereocomplexation de chaines isotactiques derivees de poly(β-propiolactones)β-substituees[J].European Polymer Journal,1989,25(4):365-369.
[16]JIANG Z,BOYER M T,SEN A.Chiral and steric recognition in optically active,isotactic,alternating.alpha.-olefincarbon monoxide copolymers.Effect on physical properties and chemical reactivity[J].Journal of the American Chemical Society,1995,117(26):7037-7038.
[17]SINGFIELD K L,BROWN G R.Optically active polyethers.1.Studies of the crystallization in blends of the enantiomers and the stereoblock form of poly(epichlorohydrin)[J].Macromolecules,1995,28(4):1290-1297.
[18]IRIBARREN I,ALEMN C,槇REGANO C,et al.Stereocopolyamides derived from 2,3-di-O-methyl-d-and-L-tartaric acids and hexamethylenediamine.2.Influence of the configurational composition on the crystal structure of optically compensated systems[J].Macromolecules,1996,29(26):8413-8424.
[19]KNNECKE K,REHAGE G.Crystallization and stereo association of stereoregular PMMA[J].Colloid&Polymer Science,1981,259(11):1062-1069.
[20]SCHOMAKER E,CHALLA G.Complexation of stereoregular poly(methyl methacrylate)14the basic structure of the stereocmoplex composed of isotactic and syndiotactic poly(methyl methacrylate)[J].Macromolecules,1989,22(8):3337-3341.
[21]KUMAKI J,KAWAUCHI T,OKOSHI K,et al.Supramolecular helical structure of the stereocomplex composed of complementary isotactic and syndiotactic poly(methyl methacrylate)s as revealed by atomic force microscopy[J].Angewandte Chemie,2007,119(28):5444-5447.
[22]CHRISTOFFERSON A J,YIAPANIS G,REN J M,et al.Molecular mapping of poly(methyl methacrylate)super-helix stereocomplexes[J].Chemical Science,2015,6(2):1370-1378.
[23]SCHOMAKER E,HOPPEN H,CHALLA G.Complexation of stereoregular poly(methyl methacrylates).11.A mechanistic model for stereocomplexation in the bulk[J].Macromolecules,1988,21(1):2195-2203.
[24]SCHOMAKER E,HOPPEN H,CHALLA G.Complexation of stereoregular poly(methyl methacrylates).12.Complexation process in dilute solution[J].Macromolecular,1988,21(1):3506-3510.
[25]KOBAYASHI J,ASAHI T,ICHIKI M,et al.Structural and optical properties of poly lactic acids[J].Journal of Applied Physics,1995,77(7):2957-2973.
[26]ZHANG J,DUAN Y,SATO H,et al.Crystal modifications and thermal behavior of poly(l-lactic acid)revealed by infrared spectroscopy[J].Macromolecules,2005,38(19):8012-8021.
[27]CARTIER L,OKIHARA T,LOTZ B.Triangular polymer single crystals:Stereocomplexes,twins,and frustrated structures[J].Macromolecules,1997,30(20):6313-6322.
[28]OKIHARA T,TSUJI M,KAWAGUCHI A,et al.Crystal structure of stereocomplex of poly(L-lactide)and poly(Dlactide)[J].Journal of Macromolecular Science Part B,1991,30(1/2):119-140.
[29]BRIZZOLARA D,CANTOW H J,DIEDERICHS K,et al.Mechanism of the stereocomplex formation between enantiomeric poly(lactide)s[J].Macromolecules,1995,29(1):191-197.
[30]BELLA J,BERMAN H M.Crystallographic evidence for C alpha-H…O C hydrogen bonds in a collagen triple helix[J].Journal of Molecular Biology,1996,264(4):734-742.
[31]JEFFREY G A,SAENGER W.Hydrogen Bonding in Biological Structures[M].Berlin:Springer,1991.
[32]ZHANG J M,SATO H,TSUJI H,et al.Infrared spectroscopic study of CH3…O C interaction during poly(l-lactide)/poly(d-lactide)stereocomplex formation[J].Macromolecules,2005,38(5):1822-1828.
[33]YANG C F,HUANG Y F,RUAN J,et al.Extensive development of precursory helical pairs prior to formation of stereocomplex crystals in racemic polylactide melt mixture[J].Macromolecules,2012,45(2):872-878.
[34]TSUJI H,IKADA Y.Stereocomplex formation between enantiomeric poly(lactic acid)s stereocomplexation from the melt[J].Macromolecules,1993,26(23):6918-6926.
[35]TSUJI H,IKADA Y.Crystallization from the melt of poly(lactide)s with different optical purities and their blends[J].Macromolecular Chemistry Physics,1996,197:3483-3499.
[36]TSUJI H,HYON S H,IKADA Y,Stereocomplex formation between enantiomeric poly(lactie)acids.4.Differential scanning calorimetric studies on precipitates from mixed solutions poly(D-lactic acid)and poly(L-lactic acid)[J].Macromolecules,1991,24:5657-5662.
[37]TSUJI H,TASHIRO K,BOUAPAO L,et al.Synchronous and separate homo-crystallization of enantiomeric poly(L-lactic acid)/poly(D-lactic acid)blends[J].Polymer,2012,53(3):747-754.
[38]PAN P,HAN L,BAO J,et al.Competitive stereocomplexation,homocrystallization,and polymorphic crystalline transition in poly(L-lactic acid)/poly(D-lactic acid)racemic blends:Molecular weight effects[J].The Journal of Physical Chemistry B,2015,119(21):6462-6470.
[39]BAO R Y,Yang W,Wei X F,et al.Enhanced formation of stereocomplex crystallites of high molecular weight poly(Llactide)/poly(D-lactide)blends from melt by using poly(ethylene glycol)[J].ACS Sustainable Chemistry&Engineering,2014,2(10):2301-2309.
[40]AURIEMMA F,ROSA C D,CAPRIO M R D,et al.Crystallization of alternating limonene oxide/carbon dioxide copolymers:Determination of the crystal structure of stereocomplex poly(limonene carbonate)[J].Macromolecules,2015,48(8):2534-2550.
[41]LIU Y,WANG M,REN W M,et al.Crystalline heterostereocomplexed polycarbonates produced from amorphous opposite enantiomers having different chemical structures[J].Angewandte Chemie International Edition,2015,54(24):7042-7046.
[42]TSUJI H,FUKUI I.Enhanced thermal stability of poly(lactide)s in the melt by enantiomeric polymer blending[J].Polymer,2003,44(10):2891-2896.
[43]ANDERSSON S R,HAKKARAINEN M,INKINEN S.Polylactide stereocomplexation leads to higher hydrolytic stability but more acidic hydrolysis product pattern[J].Biomacromolecules,2010,11(4):1067-1073.
[44]ANDERSSON S R,HAKKARAINEN M,INKINEN S,et al.Customizing the hydrolytic degradation rate of stereocomplex PLA through different PDLA architectures[J].Biomacromolecules,2012,13(4):1212-1222.
[45]WEI X F,BAO R Y,CAO Z Q,et al.Stereocomplex crystallite network in asymmetric PLLA/PDLA blends:Formation,structure,and confining effect on the crystallization rate of homocrystallites[J].Macromolecules,2014,47(4):1439-1448.
[46]NARITA J,KATAGIRI M,TSUJI H.Highly enhanced accelerating effect of melt-recrystallized stereocomplex crystallites on poly(L-lactic acid)crystallization,2-effects of poly(D-lactic acid)concentration[J].Macromolecular Materials&Engineering,2013,298(3):270-282.
[47]SAEIDLOU S,HUNEAULT M A,LI H,et al.Effect of nucleation and plasticization on the stereocomplex formation between enantiomeric poly(lactic acid)[J].Polymer,2013,54(21):5762-5770.
[48]LI W,CHEN X,MA Y,et al.Accelerating effect of starshaped poly(D-lactide)-block-poly(L-lactide)stereoblock copolymer on PLLA melting crystallization[J].CrystEngComm,2016,18:1242-1250.
[49]RATHI S R,COUGHLIN E B,HSU S L,et al.Effect of midblock on the morphology and properties of blends of ABA triblock copolymers of PDLA-mid-block-PDLA with PLLA[J].Polymer,2012,53(14):3008-3016.
[50]RATHI S R,NG D,COUGHLIN E B,et al.Effects of molecular architecture on the stereocomplex crystallization in poly(lactic acid)blends[J].Macromolecular Chemistry&Physics,2014,215(4):320-326.
[51]UEHARA H,KARAKI Y,WADA S,et al.Stereo-complex crystallization of poly(lactic acid)s in block-copolymer phase separation[J].ACS Applied Materials&Interfaces,2010,2(10):2707-2710.
[52]SUN L,GINORIO J E,ZHU L,et al.Phase transitions and honeycomb morphology in an incompatible blend of enantiomeric polylactide block copolymers[J].Macromolecules,2006,39(24):8203-8206.
[53]HU J,TANG Z,QIU X,et al.Formation of flower-or cake-shaped stereocomplex particles from the stereo multiblock copoly(rac-lactide)s[J].Biomacromolecules,2005,6(5):2843-2850.
[54]ZHANG C Y,YOU Q Y,TU X H,et al.Self-assembled pH-responsive MPEG-b-(PLA-co-PAE)block copolymer micelles for anticancer drug delivery[J].Biomaterials,2012,33(26):6273-6283.
[55]TOSHIYUKI K,MASATAKA M,KENTA K,et al.Controlled release using apolymer stereocomplex capsule through the selective extraction and incorporation of one capsule shell component[J].Langmuir,2012,28(43):15378-15384.
[56]BISHARA A,KRICHELDORF H R,DOMB A J.Stereocomplexes of triblock poly(lactide-PEG2000-lactide)as carrier of drugs[J].Macromolecular Symposia,2005,225(1):17-30.
[57]JUN Y J,PARK K M,JOUNG Y K,et al.In situ gel forming stereocomplex composed of four-arm PEG-PDLA and PEG-PLLA block copolymers[J].Macromolecular Research,2008,16(8):704-710.
[58]HIEMSTRA C,ZHONG Z,LI L,et al.In-situ formation of biodegradable hydrogels by stereocomplexation of PEG-(PLLA)(8)and PEG-(PDLA)(8)star block copolymers[J].Biomacromolecules,2006,7(10):2790-2795.
[59]ABEBE D G,TOMOKO F.Controlled thermoresponsive hydrogels by stereocomplexed PLA-PEG-PLA prepared via hybrid micelles of pre-mixed copolymers with different PEG lengths[J].Biomacromolecules,2012,13(6):1828-1836.
[60]HSU Y I,MASUTANI K,YAMAOKA T,et al.Strengthening of hydrogels made from enantiomeric block copolymers of polylactide(PLA)and poly(ethylene glycol)(PEG)by the chain extending Diels-Alder reaction at the hydrophilic PEG terminals[J].Polymer,2015,67:157-166.
[61]BRZEZINSKI M,BIELA T.Supramolecular polylactides by the cooperative interaction of the end groups and stereocomplexation[J].Macromolecules,2015,48(9):2994-3004.
[62]MA P,JIANG L,XU P,et al.Rapid stereocomplexation between enantiomeric comb-shaped cellulose-g-poly(l-lactide)nanohybrids and poly(d-lactide)from the melt[J].Biomacromolecules,2015,16(11):3723-3729.
[2]FOX T G,GARRETT B S,GOODE W E,et al.Crystalline polymers of methylmethacrylate[J].Journal of the American Chemical Society,1958,80(7):1768-1769.
[3]LOHMEYER J H G M,TAN Y Y,LAKO P,et al.Stereoselective association between isotactic poly(methylmethacrylate)and syndiotactic poly(methacrylic acid)[J].Polymer,1978,19(10):1171-1175.
[4]BOSSCHER F,KEEKSTRA D,CCHALLA G.The influence of ester groups on the stereocomplex formation between different polyalkylmethacrylates[J].Polymer,1981,22(1):124-126.
[5]LONGO J M,DICICCIO A M,COATES G W.Poly(propylene succinate):A new polymer stereocomplex[J].Journal of the American Chemical Society,2014,136(45):15897-15900.
[6]LIU Y,REN W M,WANG M,et al.Crystalline stereocomplexed polycarbonates:Hydrogen-bond-driven interlocked orderly assembly of the opposite enantiomers[J].Angewandte Chemie International Edition,2015,54(7):2241-2244.
[7]AURIEMMA F,ROSA C D,ROSARIA M,et al.Stereocomplexed poly(limonene carbonate):A unique example of the cocrystallization of amorphous enantiomeric polymers[J].Angewandte Chemie International Edition,2014,54(4):1215-1218.
[8]TSUJI H.Poly(lactide)stereocomplexes:Formation,structure,properties,degradation,and applications[J].Macromolecular Bioscience,2007,5(7):569-597.
[9]TSUBOI M,WADA A,NAGASHIMA N.Sidechainsidechain interaction between the alpha-helices of L-and Dpolypeptide chains[J].Journal of Molecular Biology,1961,3:705-706.
[10]YOSHIDA T,SAKURAI S,OKUDA T,et al.A racemic compound ofα-helical polypeptide[J].Journal of the American Chemical Society,2002,84(18):3590-3591.
[11]DUMAS P,SPASSKY N,SIGWAL P.Preparation and polymerization of racemic and optically active tert-butyl thiirane[J].Die Makromolekulare Chemie,1972,156(1):55-64.
[12]SAKAKIHARA H,TAKAHASHI Y,TADOKORO H,et al.Structural studies of isotactic poly(tert-butylethylene oxide)[J].Macromolecules,1973,6(2):205-212.
[13]GRENIER D,PRUD H R E.Complex formation between enantiomeric polyesters[J].Journal of Polymer Science Polymer Physics Edition,1984,22(4):577-587.
[14]IKADA Y,JAMSHIDI K,TSUJI H,et al.Stereocomplex formation between enantiomeric poly(lactides)[J].Macromolecules,1987,20(4):904-906.
[15]VOYER R,PRUD H R E.Stereocomplexation de chaines isotactiques derivees de poly(β-propiolactones)β-substituees[J].European Polymer Journal,1989,25(4):365-369.
[16]JIANG Z,BOYER M T,SEN A.Chiral and steric recognition in optically active,isotactic,alternating.alpha.-olefincarbon monoxide copolymers.Effect on physical properties and chemical reactivity[J].Journal of the American Chemical Society,1995,117(26):7037-7038.
[17]SINGFIELD K L,BROWN G R.Optically active polyethers.1.Studies of the crystallization in blends of the enantiomers and the stereoblock form of poly(epichlorohydrin)[J].Macromolecules,1995,28(4):1290-1297.
[18]IRIBARREN I,ALEMN C,槇REGANO C,et al.Stereocopolyamides derived from 2,3-di-O-methyl-d-and-L-tartaric acids and hexamethylenediamine.2.Influence of the configurational composition on the crystal structure of optically compensated systems[J].Macromolecules,1996,29(26):8413-8424.
[19]KNNECKE K,REHAGE G.Crystallization and stereo association of stereoregular PMMA[J].Colloid&Polymer Science,1981,259(11):1062-1069.
[20]SCHOMAKER E,CHALLA G.Complexation of stereoregular poly(methyl methacrylate)14the basic structure of the stereocmoplex composed of isotactic and syndiotactic poly(methyl methacrylate)[J].Macromolecules,1989,22(8):3337-3341.
[21]KUMAKI J,KAWAUCHI T,OKOSHI K,et al.Supramolecular helical structure of the stereocomplex composed of complementary isotactic and syndiotactic poly(methyl methacrylate)s as revealed by atomic force microscopy[J].Angewandte Chemie,2007,119(28):5444-5447.
[22]CHRISTOFFERSON A J,YIAPANIS G,REN J M,et al.Molecular mapping of poly(methyl methacrylate)super-helix stereocomplexes[J].Chemical Science,2015,6(2):1370-1378.
[23]SCHOMAKER E,HOPPEN H,CHALLA G.Complexation of stereoregular poly(methyl methacrylates).11.A mechanistic model for stereocomplexation in the bulk[J].Macromolecules,1988,21(1):2195-2203.
[24]SCHOMAKER E,HOPPEN H,CHALLA G.Complexation of stereoregular poly(methyl methacrylates).12.Complexation process in dilute solution[J].Macromolecular,1988,21(1):3506-3510.
[25]KOBAYASHI J,ASAHI T,ICHIKI M,et al.Structural and optical properties of poly lactic acids[J].Journal of Applied Physics,1995,77(7):2957-2973.
[26]ZHANG J,DUAN Y,SATO H,et al.Crystal modifications and thermal behavior of poly(l-lactic acid)revealed by infrared spectroscopy[J].Macromolecules,2005,38(19):8012-8021.
[27]CARTIER L,OKIHARA T,LOTZ B.Triangular polymer single crystals:Stereocomplexes,twins,and frustrated structures[J].Macromolecules,1997,30(20):6313-6322.
[28]OKIHARA T,TSUJI M,KAWAGUCHI A,et al.Crystal structure of stereocomplex of poly(L-lactide)and poly(Dlactide)[J].Journal of Macromolecular Science Part B,1991,30(1/2):119-140.
[29]BRIZZOLARA D,CANTOW H J,DIEDERICHS K,et al.Mechanism of the stereocomplex formation between enantiomeric poly(lactide)s[J].Macromolecules,1995,29(1):191-197.
[30]BELLA J,BERMAN H M.Crystallographic evidence for C alpha-H…O C hydrogen bonds in a collagen triple helix[J].Journal of Molecular Biology,1996,264(4):734-742.
[31]JEFFREY G A,SAENGER W.Hydrogen Bonding in Biological Structures[M].Berlin:Springer,1991.
[32]ZHANG J M,SATO H,TSUJI H,et al.Infrared spectroscopic study of CH3…O C interaction during poly(l-lactide)/poly(d-lactide)stereocomplex formation[J].Macromolecules,2005,38(5):1822-1828.
[33]YANG C F,HUANG Y F,RUAN J,et al.Extensive development of precursory helical pairs prior to formation of stereocomplex crystals in racemic polylactide melt mixture[J].Macromolecules,2012,45(2):872-878.
[34]TSUJI H,IKADA Y.Stereocomplex formation between enantiomeric poly(lactic acid)s stereocomplexation from the melt[J].Macromolecules,1993,26(23):6918-6926.
[35]TSUJI H,IKADA Y.Crystallization from the melt of poly(lactide)s with different optical purities and their blends[J].Macromolecular Chemistry Physics,1996,197:3483-3499.
[36]TSUJI H,HYON S H,IKADA Y,Stereocomplex formation between enantiomeric poly(lactie)acids.4.Differential scanning calorimetric studies on precipitates from mixed solutions poly(D-lactic acid)and poly(L-lactic acid)[J].Macromolecules,1991,24:5657-5662.
[37]TSUJI H,TASHIRO K,BOUAPAO L,et al.Synchronous and separate homo-crystallization of enantiomeric poly(L-lactic acid)/poly(D-lactic acid)blends[J].Polymer,2012,53(3):747-754.
[38]PAN P,HAN L,BAO J,et al.Competitive stereocomplexation,homocrystallization,and polymorphic crystalline transition in poly(L-lactic acid)/poly(D-lactic acid)racemic blends:Molecular weight effects[J].The Journal of Physical Chemistry B,2015,119(21):6462-6470.
[39]BAO R Y,Yang W,Wei X F,et al.Enhanced formation of stereocomplex crystallites of high molecular weight poly(Llactide)/poly(D-lactide)blends from melt by using poly(ethylene glycol)[J].ACS Sustainable Chemistry&Engineering,2014,2(10):2301-2309.
[40]AURIEMMA F,ROSA C D,CAPRIO M R D,et al.Crystallization of alternating limonene oxide/carbon dioxide copolymers:Determination of the crystal structure of stereocomplex poly(limonene carbonate)[J].Macromolecules,2015,48(8):2534-2550.
[41]LIU Y,WANG M,REN W M,et al.Crystalline heterostereocomplexed polycarbonates produced from amorphous opposite enantiomers having different chemical structures[J].Angewandte Chemie International Edition,2015,54(24):7042-7046.
[42]TSUJI H,FUKUI I.Enhanced thermal stability of poly(lactide)s in the melt by enantiomeric polymer blending[J].Polymer,2003,44(10):2891-2896.
[43]ANDERSSON S R,HAKKARAINEN M,INKINEN S.Polylactide stereocomplexation leads to higher hydrolytic stability but more acidic hydrolysis product pattern[J].Biomacromolecules,2010,11(4):1067-1073.
[44]ANDERSSON S R,HAKKARAINEN M,INKINEN S,et al.Customizing the hydrolytic degradation rate of stereocomplex PLA through different PDLA architectures[J].Biomacromolecules,2012,13(4):1212-1222.
[45]WEI X F,BAO R Y,CAO Z Q,et al.Stereocomplex crystallite network in asymmetric PLLA/PDLA blends:Formation,structure,and confining effect on the crystallization rate of homocrystallites[J].Macromolecules,2014,47(4):1439-1448.
[46]NARITA J,KATAGIRI M,TSUJI H.Highly enhanced accelerating effect of melt-recrystallized stereocomplex crystallites on poly(L-lactic acid)crystallization,2-effects of poly(D-lactic acid)concentration[J].Macromolecular Materials&Engineering,2013,298(3):270-282.
[47]SAEIDLOU S,HUNEAULT M A,LI H,et al.Effect of nucleation and plasticization on the stereocomplex formation between enantiomeric poly(lactic acid)[J].Polymer,2013,54(21):5762-5770.
[48]LI W,CHEN X,MA Y,et al.Accelerating effect of starshaped poly(D-lactide)-block-poly(L-lactide)stereoblock copolymer on PLLA melting crystallization[J].CrystEngComm,2016,18:1242-1250.
[49]RATHI S R,COUGHLIN E B,HSU S L,et al.Effect of midblock on the morphology and properties of blends of ABA triblock copolymers of PDLA-mid-block-PDLA with PLLA[J].Polymer,2012,53(14):3008-3016.
[50]RATHI S R,NG D,COUGHLIN E B,et al.Effects of molecular architecture on the stereocomplex crystallization in poly(lactic acid)blends[J].Macromolecular Chemistry&Physics,2014,215(4):320-326.
[51]UEHARA H,KARAKI Y,WADA S,et al.Stereo-complex crystallization of poly(lactic acid)s in block-copolymer phase separation[J].ACS Applied Materials&Interfaces,2010,2(10):2707-2710.
[52]SUN L,GINORIO J E,ZHU L,et al.Phase transitions and honeycomb morphology in an incompatible blend of enantiomeric polylactide block copolymers[J].Macromolecules,2006,39(24):8203-8206.
[53]HU J,TANG Z,QIU X,et al.Formation of flower-or cake-shaped stereocomplex particles from the stereo multiblock copoly(rac-lactide)s[J].Biomacromolecules,2005,6(5):2843-2850.
[54]ZHANG C Y,YOU Q Y,TU X H,et al.Self-assembled pH-responsive MPEG-b-(PLA-co-PAE)block copolymer micelles for anticancer drug delivery[J].Biomaterials,2012,33(26):6273-6283.
[55]TOSHIYUKI K,MASATAKA M,KENTA K,et al.Controlled release using apolymer stereocomplex capsule through the selective extraction and incorporation of one capsule shell component[J].Langmuir,2012,28(43):15378-15384.
[56]BISHARA A,KRICHELDORF H R,DOMB A J.Stereocomplexes of triblock poly(lactide-PEG2000-lactide)as carrier of drugs[J].Macromolecular Symposia,2005,225(1):17-30.
[57]JUN Y J,PARK K M,JOUNG Y K,et al.In situ gel forming stereocomplex composed of four-arm PEG-PDLA and PEG-PLLA block copolymers[J].Macromolecular Research,2008,16(8):704-710.
[58]HIEMSTRA C,ZHONG Z,LI L,et al.In-situ formation of biodegradable hydrogels by stereocomplexation of PEG-(PLLA)(8)and PEG-(PDLA)(8)star block copolymers[J].Biomacromolecules,2006,7(10):2790-2795.
[59]ABEBE D G,TOMOKO F.Controlled thermoresponsive hydrogels by stereocomplexed PLA-PEG-PLA prepared via hybrid micelles of pre-mixed copolymers with different PEG lengths[J].Biomacromolecules,2012,13(6):1828-1836.
[60]HSU Y I,MASUTANI K,YAMAOKA T,et al.Strengthening of hydrogels made from enantiomeric block copolymers of polylactide(PLA)and poly(ethylene glycol)(PEG)by the chain extending Diels-Alder reaction at the hydrophilic PEG terminals[J].Polymer,2015,67:157-166.
[61]BRZEZINSKI M,BIELA T.Supramolecular polylactides by the cooperative interaction of the end groups and stereocomplexation[J].Macromolecules,2015,48(9):2994-3004.
[62]MA P,JIANG L,XU P,et al.Rapid stereocomplexation between enantiomeric comb-shaped cellulose-g-poly(l-lactide)nanohybrids and poly(d-lactide)from the melt[J].Biomacromolecules,2015,16(11):3723-3729.