脂肪族聚酯具有生物可降解、生物相容及环境友好等优良性能，其已广泛应用于包装、农用地膜、生物医用材料等领域。与缩聚反应相比，内酯开环聚合反应条件温和，无小分子产生，容易制得高分子量、窄分子量分布的聚合物。目前，脂肪族聚酯主要通过配位聚合反应制备，通常使用金属配合物作为催化剂，所得聚合物中含有少量无法除去的金属离子，这限制了其在医用材料等领域的应用。与金属催化剂相比，非金属有机催化剂具有价廉、易制备、低毒等特点，因此非金属有机催化剂催化的内酯开环聚合反应受到了研究者的广泛关注。本文根据非金属有机催化剂作用机理的不同，从氢键作用机理出发，综述近年来基于氢键作用的非金属有机催化剂在内酯开环聚合领域的研究进展。
Aliphatic polyesters are a class of biodegradable, biocompatible, and environmentally friendly polymers, which have been widely used in many fields, such as packaging, agricultural film, biomedical materials, etc. In comparison with the polycondensation reaction, the ring-opening polymerization (ROP) of lactones could be conducted in mild conditions with no small-molecular byproducts formed in the polymerization process. In addition, ROP of lactones is suitable to synthesize the aliphatic polyesters with high molecular weight and narrow molecular weight distribution. At present, the aliphatic polyesters are usually synthesized by the coordination polymerization with the metal complexes as catalysts. The as-prepared polymers inevitably contain a small amount of metal ions that are difficult to be removed completely, which limits the applications of aliphatic polyesters in the biomedical fields. Due to the low cost, ease of preparation, and low toxicity of non-metallic organocatalysts, the ROP of lactones catalyzed by non-metallic organocatalysts has drawn much attention in recent years. According to the catalytic mechanisms, this paper will focus on the non-metallic organocatalysts with the hydrogen-bonding interactions and review the recent research progress on the hydrogen bonding-based non-metallic organocatalysts used for ROP of lactones.
Contents
1 Introduction
2 Monofunctional hydrogen-bonding catalysts
2.1 DBU
2.2 MTBD
2.3 Phosphazenes
3 Bifunctional hydrogen-bonding catalysts
3.1 4-Dimethylaminopyridine
3.2 Thiourea-amine catalyst
3.3 1,5,7-Triazabicyclo[4.4.0] dec-5-ene
3.4 Other bifunctional catalysts
4 Combined catalyst systems
4.1 Combined neutral catalyst systems
4.2 Combined ionic catalyst systems
5 Conclusion
[1] Gross R A, Kalra B. Science, 2002, 297(5582):803.
[2] Albertsson A C, Varma I K. Biomacromolecules, 2003, 4(6):1466.
[3] Mecking S. Angew. Chem. Int. Ed., 2004, 43(9):1078.
[4] Luckachan G E, Pillai C K S. J. Polym. Environ., 2011, 19(3):637.
[5] Zhu Y Q, Romain C, Williams C K. Nature, 2016, 540(7633):354.
[6] Tong R. Ind. Eng. Chem. Res., 2017, 56(15):4207.
[7] Lecomte P, Jerome C. Adv. Polym. Sci., 2012, 245:173.
[8] Nuyken O, Pask S D. Polymers, 2013, 5(2):361.
[9] Dutta S, Hung W C, Huang B H, Lin C C. Adv. Polym. Sci., 2012, 245:219.
[10] Han L, Shan G, Bao Y, Pan P. J. Phys. Chem. B, 2015, 119(44):14270.
[11] Li J, Deng Y, Jie S, Li B G. J. Organomet. Chem., 2015, 797:76.
[12] Wang R B, Zhang J W, Yin Q, Xu Y X, Cheng J J, Tong R. Angew. Chem. Int. Ed., 2016, 55(42):13010.
[13] Rosen T, Goldberg I, Venditto V, Kol M. J. Am. Chem. Soc., 2016, 138(37):12041.
[14] Rosen T, Goldberg I, Navarra W, Venditto V, Kol M. Chem. Sci., 2017, 8(8):5476.
[15] Bakewell C, Cao T P A, Le Goff X F, Long N J, Auffrant A, Williams C K. Organometallics, 2013, 32(5):1475.
[16] Li L, Liu B, Liu D T, Wu C J, Li S H, Liu B, Cui D M. Organometallics, 2014, 33(22):6474.
[17] Dove A P. ACS Macro Lett., 2012, 1(12):1409.
[18] Jeffrey G A. An Introduction to Hydrogen Bonding. Oxford University Press, 1997.
[19] Gilli G, Gilli P. The Nature of the Hydrogen Bond. Oxford University Press, 2009.
[20] Kiesewetter M K, Shin E J, Hedrick J L, Waymouth R M. Macromolecules, 2010, 43(5):2093.
[21] Ottou W N, Sardon H, Mecerreyes D, Vignolle J, Taton D. Prog. Polym. Sci., 2016, 56:64.
[22] Connor E F, Nyce G W, Myers M, Mock A, Hedrick J L. J. Am. Chem. Soc., 2002, 124(6):914.
[23] Kamber N E, Jeong W, Gonzalez S, Hedrick J L, Waymouth R M. Macromolecules, 2009, 42(5):1634.
[24] Myers M, Connor E F, Glauser T, Mock A, Nyce G, Hedrick J L. J. Polym. Sci. Part A:Polym. Chem., 2002, 40(7):844.
[25] Lohmeijer B G G, Pratt R C, Leibfarth F, Logan J W, Long D A, Dove A P, Nederberg F, Choi J, Wade C, Waymouth R M, Hedrick J L. Macromolecules, 2006, 39(25):8574.
[26] Carafa M, Mesto E, Quaranta E. Eur. J. Org. Chem., 2011, (13):2458.
[27] Brown H A, De Crisci A G, Hedrick J L, Waymouth R M. ACS Macro Lett., 2012, 1(9):1113.
[28] Sherck N J, Kim H C, Won Y Y. Macromolecules, 2016, 49(13):4699.
[29] Kaljurand I, Kutt A, Soovali L, Rodima T, Maemets V, Leito I, Koppel I A. J. Org. Chem., 2005, 70(3):1019.
[30] Zhang L, Nederberg F, Pratt R C, Waymouth R M, Hedrick J L, Wade C G. Macromolecules, 2007, 40(12):4154.
[31] Zhang L, Nederberg F, Messman J, Pratt R C, Hedrick J L, Wade C G. J. Am. Chem. Soc., 2007, 129(42):12610.
[32] Helou M, Miserque O, Brusson J M, Carpentier J F, Guillaume S M. Chem. Eur. J., 2010, 16(46):13805.
[33] Yang H J, Yan M Q, Pispas S, Zhang G Z. Macromol. Chem. Phys., 2011, 212(23):2589.
[34] Memeger W, Campbell G C, Davidson F. Macromolecules, 1996, 29(20):6475.
[35] Illy N, Boileau S, Buchmann W, Penelle J, Barbier V. Macromolecules, 2010, 43(21):8782.
[36] Hong M, Chen E Y X. Angew. Chem. Int. Ed., 2016, 55(13):4188.
[37] Jaffredo C G, Carpentier J F, Guillaume S M. Macromol. Rapid Comm., 2012, 33(22):1938.
[38] Nederberg F, Connor E F, Moller M, Glauser T, Hedrick J L. Angew. Chem. Int. Ed., 2001, 40(14):2712.
[39] Bonduelle C, Martin-Vaca B, Cossio F P, Bourissou D. Chem. Eur. J., 2008, 14(17):5304.
[40] Dove A P, Pratt R C, Lohmeijer B G G, Waymouth R M, Hedrick J L. J. Am. Chem. Soc., 2005, 127(40):13798.
[41] Simon L, Goodman J M. J. Org. Chem., 2007, 72(25):9656.
[42] Chuma A, Horn H W, Swope W C, Pratt R C, Zhang L, Lohmeijer B G G, Wade C G, Waymouth R M, Hedrick J L, Rice J E. J. Am. Chem. Soc., 2008, 130(21):6749.
[43] Pratt R C, Lohmeijer B G G, Long D A, Waymouth R M, Hedrick J L. J. Am. Chem. Soc., 2006, 128(14):4556.
[44] Kiesewetter M K, Scholten M D, Kirn N, Weber R L, Hedrick J L, Waymouth R M. J. Org. Chem., 2009, 74(24):9490.
[45] Kricheldorf H R, Dunsing R. Makromol. Chem., 1986, 187(7):1611.
[46] Susperregui N, Delcroix D, Martin-Vaca B, Bourissou D, Maron L. J. Org. Chem., 2010, 75(19):6581.
[47] Delcroix D, Couffin A, Susperregui N, Navarro C, Maron L, Martin-Vaca B, Bourissou D. Polym. Chem., 2011, 2(10):2249.
[48] Rostami A, Sadeh E, Ahmadi S. J. Polym. Sci. Part A:Polym. Chem., 2017, 55(15):2483.
[49] Specklin D, Hild F, Chen L, Thévenin L, Munch M, Dumas F, Le Bideau F, Dagorne S. ChemCatChem, 2017, 9:1.
[50] Coady D J, Engler A C, Horn H W, Bajjuri K M, Fukushima K, Jones G O, Nelson A, Rice J E, Hedrick J L. ACS Macro Lett., 2012, 1(1):19.
[51] Kazakov O I, Kiesewetter M K. Macromolecules, 2015, 48(17):6121.
[52] Spink S S, Kazakov O I, Kiesewetter E T, Kiesewetter M K. Macromolecules, 2015, 48(17):6127.
[53] Fastnacht K V, Spink S S, Dharmaratne N U, Pothupitiya J U, Datta P P, Kiesewetter E T, Kiesewetter M K. ACS Macro Lett., 2016, 5(8):982.
[54] Dharmaratne N U, Pothupitiya J U, Bannin T J, Kazakov O I, Kiesewetter M K. ACS Macro Lett., 2017, 6(4):421.
[55] Coulembier O, Sanders D R, Nelson A, Hollenbeck A N, Horn H W, Rice J E, Fujiwara M, Dubois P, Hedrick J L. Angew. Chem. Int. Ed., 2009, 48(28):5170.
[56] Alba A, Schopp A, Delgado A P D S, Cherif-Cheikh R, Martin-Vaca B, Bourissou D. J. Polym. Sci., Part A:Polym. Chem., 2010, 48(4):959.
[57] Liu J, Chen C, Li Z, Wu W, Zhi X, Zhang Q, Wu H, Wang X, Cui S, Guo K. Polym. Chem., 2015, 6(20):3754.
[58] Nickerson D M, Angeles V V, Auvil T J, So S S, Mattson A E. Chem. Commun., 2013, 49(39):4289.
[59] Xu S, Sun H, Liu J, Xu J, Pan X, Dong H, Liu Y, Li Z, Guo K. Polym. Chem., 2016, 7(44):6843.
[60] Makiguchi K, Kikuchi S, Yanai K, Ogasawara Y, Sato, S I, Satoh T, Kakuchi T. J. Polym. Sci., Part A:Polym. Chem., 2014, 52(7):1047.
[61] Wang X, Cui S D, Li Z J, Kan S L, Zhang Q G, Zhao C X, Wu H, Liu J J, Wu W Z, Guo K. Polym. Chem., 2014, 5(20):6051.
[62] Wang X, Liu J Q, Xu S Q, Xu J X, Pan X F, Liu J J, Cui S D, Li Z J, Guo K. Polym. Chem., 2016, 7(41):6297.
[63] Zhang D W, Jardel D, Peruch F, Calin N, Dufaud V, Dutasta J P, Martinez A, Bibal B. Eur. J. Org. Chem., 2016, (8):1619.
[64] Zhang X Y, Jones G O, Hedrick J L, Waymouth R M. Nat. Chem., 2016, 8(11):1047.
[65] Lin B H, Waymouth R M. J. Am. Chem. Soc., 2017, 139(4):1645.
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