Polymers from macrolactones: From pheromones to functional materials

Progress in Polymer Science - Tập 91 - Trang 29-50 - 2019
James A. Wilson1, Zeliha Ates2, Robin L. Pflughaupt3, Andrew P. Dove3, Andreas Heise2
1Department of Chemistry, Royal College of Surgeons in Ireland (RCSI), 123 St. Stephen’s Green, Dublin 2, Ireland
2School of Chemical Sciences, Dublin City University, Dublin, Ireland
3School of Chemistry University of Birmingham, Edgbaston, Birmingham B15 2TT, UK

Tài liệu tham khảo

Albertsson, 2003, Recent developments in ring opening polymerization of lactones for biomedical applications, Biomacromolecules, 4, 1466, 10.1021/bm034247a Place, 2009, Synthetic polymer scaffolds for tissue engineering, Chem Soc Rev, 38, 1139, 10.1039/b811392k Uhrich, 1999, Polymeric systems for controlled drug release, Chem Rev, 99, 3181, 10.1021/cr940351u Yevstropov, 1983, Thermodynamics of pentadecalactone, of the process of its polymerization and of formed polypentadecalactone in the 0-k-400-k region, Vysokomol Soedin Ser A, 25, 1679 Lebedev, 1984, Thermodynamic properties of polylactones, Makromol Chem-Macromol Chem Phys, 185, 1235, 10.1002/macp.1984.021850617 Nomura, 1994, Anionic ring-opening polymerization of macrocyclic esters, Macromolecules, 27, 620, 10.1021/ma00080a046 Jedlinski, 1996, Anionic polymerization of pentadecanolide. A new route to a potentially biodegradable aliphatic polyester, Macromol Chem Phys, 197, 2923, 10.1002/macp.1996.021970925 Williams, 1999, The synthesis of macrocyclic musks, Synthesis, 1707, 10.1055/s-1999-3581 Kraft, 2000, Odds and trends: recent developments in the chemistry of odorants, Angew Chem Int Ed, 39, 2980, 10.1002/1521-3773(20000901)39:17<2980::AID-ANIE2980>3.0.CO;2-# Witt, 2013, Large-ring lactones from plant oils, Green Chem, 15, 2361, 10.1039/c3gc40905h Kerschbaum, 1927, Large lactone rings - the carriers of the musky vegetable aroma, Ber Dtsch Chem Ges, 60, 902, 10.1002/cber.19270600411 Parenty, 2013, Update 1 of: macrolactonizations in the total synthesis of natural products, Chem Rev, 113, 10.1021/cr300129n McGinty, 2011, Fragrance material review on α-pentadecalactone, Food Chem Toxicol, 49, S193, 10.1016/j.fct.2011.07.026 Grammer, 1993, 5-α-androst-16en-3α-on: a male pheromone? A brief report, Ethol Sociobiol, 14, 201, 10.1016/0162-3095(93)90006-4 Amoore, 1977, Specific anosmias To 5-α-androst-16-En-3-one and ω-pentadecalactone - urinous and musky primary odors, Chem Sens Flav, 2, 401, 10.1093/chemse/2.4.401 Skoglund, 1998, Thermophysical properties of polypentadecanolactone, Polymer, 39, 1899, 10.1016/S0032-3861(97)00473-4 Skoglund, 1998, Crystallization kinetics of polytridecanolactone and polypentadecanolactone, Polymer, 39, 3143, 10.1016/S0032-3861(97)10023-4 Focarete, 2001, Physical characterization of poly(omega-pentadecalactone) synthesized by lipase-catalyzed ring-opening polymerization, J Polym Sci Part B Polym Phys, 39, 1721, 10.1002/polb.1145 Cai, 2010, Effects of molecular weight on poly(ω-pentadecalactone) mechanical and thermal properties, Polymer, 51, 1088, 10.1016/j.polymer.2010.01.007 Flory, 1946, Fundamental principles of condensation polymerization, Chem Rev, 39, 137, 10.1021/cr60122a003 Quinzler, 2010, Linear semicrystalline polyesters from fatty acids by complete feedstock molecule utilization, Angew Chem Int Ed, 49, 4306, 10.1002/anie.201001510 Liu, 2011, Polymers from fatty acids: poly(ω-hydroxyl tetradecanoic acid) synthesis and physico-mechanical studies, Biomacromolecules, 12, 3291, 10.1021/bm2007554 Stempfle, 2011, Long-chain linear C-19 and C-23 monomers and polycondensates from unsaturated fatty acid esters, Macromolecules, 44, 4159, 10.1021/ma200627e Vilela, 2012, Meier MAR. Plant oil-based long-chain C-26 monomers and their polymers, Macromol Chem Phys, 213, 2220, 10.1002/macp.201200332 Mutlu, 2013, Self-metathesis of fatty acid methyl esters: full conversion by choosing the appropriate plant oil, RSC Adv, 3, 4927, 10.1039/c3ra40330k Rybak, 2008, Acyclic diene metathesis with a monomer from renewable resources: control of molecular weight and one-step preparation of block copolymers, ChemSusChem, 1, 542, 10.1002/cssc.200800047 Fokou, 2010, Studying and suppressing olefin isomerization side reactions during ADMET polymerizations, Macromol Rapid Commun, 31, 368, 10.1002/marc.200900678 Trzaskowski, 2011, Aliphatic long-chain C-20 polyesters from olefin metathesis, Macromol Rapid Commun, 32, 1352, 10.1002/marc.201100319 Turunc, 2011, Renewable polyethylene mimics derived from Castor oil, Macromol Rapid Commun, 32, 1357, 10.1002/marc.201100280 Kreye, 2011, Introducing multicomponent reactions to polymer science: Passerini reactions of renewable monomers, J Am Chem Soc, 133, 1790, 10.1021/ja1113003 de Espinosa, 2011, Plant oils: the perfect renewable resource for polymer science?, Eur Polym J, 47, 837, 10.1016/j.eurpolymj.2010.11.020 Akintayo, 2012, Acyclic triene metathesis polymerization of Plukenetia conophora oil: branched polymers by direct polymerization of renewable resources, Macromol Chem Phys, 213, 87, 10.1002/macp.201100539 Pepels, 2013, From polyethylene to polyester: influence of ester groups on the physical properties, Macromolecules, 46, 7668, 10.1021/ma401403x Turunc, 2011, Thiol-ene vs. ADMET: a complementary approach to fatty acid-based biodegradable polymers, Green Chem, 13, 314, 10.1039/c0gc00773k Dubois, 2009 Dove, 2008, Controlled ring-opening polymerization of cyclic esters: polymer blocks in self-assembled nanostructures, Chem Commun, 122, 6446, 10.1039/b813059k Pepels, 2014, Theoretical and experimental approach to accurately predict the complex molecular weight distribution in the polymerization of strainless cyclic esters, Macromolecules, 47, 5542, 10.1021/ma5015353 Kobayashi, 2001, Enzymatic polymerization, Chem Rev, 101, 3793, 10.1021/cr990121l Champagne, 2016, Recent developments and optimization of lipase-catalyzed lactone formation and ring-opening polymerization, Macromol Rapid Commun, 37, 1986, 10.1002/marc.201600494 Uyama, 1993, Enzymatic ring-opening polymerization of lactones catalyzed by lipase, Chem Lett, 1149, 10.1246/cl.1993.1149 Knani, 1993, Enzymatic polyesterification in organic media. Enzyme-catalyzed synthesis of linear polyesters. I. Condensation polymerization of linear hydroxyesters. II. Ring-opening polymerization of ε-caprolactone, J Polym Sci Part A Polym Chem, 31, 1221, 10.1002/pola.1993.080310518 MacDonald, 1995, Enzyme-catalyzed ε-Caprolactone ring-opening polymerization, Macromolecules, 28, 73, 10.1021/ma00105a008 Uyama, 1993, Synthesis of polyesters by enzymatic ring-opening copolymerization using lipase catalyst, P Jpn Acad B Phys, 69, 203, 10.2183/pjab.69.203 Uyama, 1995, Lipase-catalyzed ring-opening polymerization of 12-Dodecanolide, Macromolecules, 28, 7046, 10.1021/ma00125a002 Uyama, 1995, Enzymatic ring-opening polymerization of lactones to polyesters by lipase catalyst - unusually high reactivity of Macrolides, Bull Chem Soc Jpn, 68, 56, 10.1246/bcsj.68.56 Uyama, 1996, Lipase-catalyzed ring-opening polymerization and copolymerization of 15-pentadecanolide, Acta Polym, 47, 357, 10.1002/actp.1996.010470807 Noda, 1997, Enzymatic polymerization catalyzed by surfactant-coated lipases in organic media, Biotechnol Lett, 19, 307, 10.1023/A:1018334430266 Uyama, 2002, High-performance immobilized lipase catalyst for polyester synthesis, Polym J, 34, 970, 10.1295/polymj.34.970 Bisht, 1997, Enzyme-catalyzed ring-opening polymerization of ω-Pentadecalactone, Macromolecules, 30, 2705, 10.1021/ma961869y Kundys, 2018, Candida antarctica Lipase B as Catalyst for Cyclic Esters Synthesis, Their Polymerization and Degradation of Aliphatic Polyesters, J Polym Environ, 26, 396, 10.1007/s10924-017-0945-1 Polloni, 2018, Polyesters from macrolactones using commercial lipase NS 88011 and novozym 435 as biocatalysts, Appl Biochem Biotechnol, 184, 659, 10.1007/s12010-017-2583-4 Hunsen, 2007, A cutinase with polyester synthesis activity, Macromolecules, 40, 148, 10.1021/ma062095g Hunsen, 2008, Humicola insolens cutinase-catalyzed lactone ring-opening Polymerizations: kinetic and mechanistic studies, Biomacromolecules, 9, 518, 10.1021/bm701269p Herrera-Kao, 2015, Effect of reaction temperature on the physicochemical properties of poly(pentadecanolide) obtained by enzyme-catalyzed ring-opening polymerization, Polym Bull, 72, 441, 10.1007/s00289-014-1288-x Matsumoto, 1999, Kinetics of ring-opening polymerization of lactones by lipase, Biochem Eng J, 4, 73, 10.1016/S1369-703X(99)00017-0 Hedfors, 2010, Lipase chemoselectivity towards alcohol and thiol acyl acceptors in a transacylation reaction, J Mol Catal, B Enzym, 66, 120, 10.1016/j.molcatb.2010.04.005 Nakane, 2008, Blends of poly(L-lactic acid) with poly(ω-pentadecalactone) synthesized by enzyme-catalyzed polymerization, J Appl Polym Sci, 108, 2139, 10.1002/app.27838 Kumar, 2000, Efficient ring-opening polymerization and copolymerization of ε-caprolactone and ω-pentadecalactone catalyzed by Candida antartica lipase B, Macromolecules, 33, 6303, 10.1021/ma000344+ Varma, 2005, Enzyme catalyzed synthesis of polyesters, Prog Polym Sci, 30, 949, 10.1016/j.progpolymsci.2005.06.010 Mei, 2003, Kinetics and mechanism of Candida antarctica lipase B catalyzed solution polymerization of ε-Caprolactone, Macromolecules, 36, 5530, 10.1021/ma025741u Albertsson, 2008, Recent developments in enzyme-catalyzed ring-opening polymerization, Adv Drug Deliv Rev, 60, 1077, 10.1016/j.addr.2008.02.007 Kobayashi, 2010, Lipase-catalyzed polyester synthesis – a green polymer chemistry, P Jpn Acad B Phys, 86, 338, 10.2183/pjab.86.338 Kobayashi, 1998, In vitro biosynthesis of polyesters with isolated enzymes in aqueous systems and organic solvents, Polym Degrad Stabil, 59, 195, 10.1016/S0141-3910(97)00178-X Namekawa, 1998, Lipase-catalyzed ring-opening polymerization of 16-hexadecanolide, P Jpn Acad B Phys, 74, 65, 10.2183/pjab.74.65 Namekawa, 1999, Lipase-catalyzed ring-opening polymerization of lactones to polyesters and its mechanistic aspects, Int J Biol Macromol, 25, 145, 10.1016/S0141-8130(99)00028-8 Duda, 2002, Kinetics of the ring-opening polymerization of 6-, 7-, 9-, 12-, 13-, 16-, and 17-membered lactones. Comparison of chemical and enzymatic polymerizations, Macromolecules, 35, 4266, 10.1021/ma012207y van der Mee, 2006, Investigation of lipase-catalyzed ring-opening polymerizations of Lactones with various ring sizes: kinetic evaluation, Macromolecules, 39, 5021, 10.1021/ma060668j Witt, 2017, No strain, no gain? Enzymatic ring‐opening polymerization of strainless aliphatic macrolactones, Macromol Rapid Commun, 38, 10.1002/marc.201600638 Kikuchi, 2002, Lipase-catalyzed ring-opening polymerization of substituted lactones, Polym J, 34, 835, 10.1295/polymj.34.835 Taden, 2003, Enzymatic polymerization towards biodegradable polyester nanoparticles, Macromol Rapid Commun, 24, 512, 10.1002/marc.200390079 Målberg, 2010, The environmental influence in enzymatic polymerization of aliphatic polyesters in bulk and aqueous mini-emulsion, Polymer, 51, 5318, 10.1016/j.polymer.2010.09.016 Panlawan, 2013, Lipase-catalyzed interfacial polymerization of ω-pentadecalactone in aqueous biphasic medium: a mechanistic study, J Mol Catal, B Enzym, 88, 69, 10.1016/j.molcatb.2012.11.008 Chiaradia, 2018, Polyester nanoparticles from macrolactones via miniemulsion enzymatic ring-opening polymerization, Colloid Polym Sci, 296, 861, 10.1007/s00396-018-4306-y Spinella, 2015, Enzymatic reactive extrusion: moving towards continuous enzyme-catalysed polyester polymerization and processing, Green Chem, 17, 4146, 10.1039/C5GC00992H Wosnick, 2010, Enzymatic ring-opening polymerization in a continuous-flow system, Abstr Pap Am Chem Soc, 240 Polloni, 2017, Enzymatic ring opening polymerization of ω-Pentadecalactone in different solvents in a variable-volume view reactor, J Polym SciPart A Polym Chem, 55, 1219, 10.1002/pola.28486 Rebelatto, 2018, High-pressure phase equilibrium data for systems containing carbon dioxide, ω-pentadecalactone, chloroform and water, J Chem Thermodyn, 122, 125, 10.1016/j.jct.2018.03.008 Polloni, 2017, Enzymatic ring opening polymerization of ω-pentadecalactone using supercritical carbon dioxide, J Supercrit Fluids, 119, 221, 10.1016/j.supflu.2016.09.019 Guindani, 2017, Enzymatic ring opening copolymerization of globalide and ε-caprolactone under supercritical conditions, J Supercrit Fluids, 128, 404, 10.1016/j.supflu.2017.06.008 Gualandi, 2010, Scaffold for tissue engineering fabricated by non-isothermal supercritical carbon dioxide foaming of a highly crystalline polyester, Acta Biomater, 6, 130, 10.1016/j.actbio.2009.07.020 Hunley, 2013, Microstructure analysis and model discrimination of enzyme-catalyzed copolyesters, ACS Macro Lett, 2, 375, 10.1021/mz300659h Kumar, 2000, Candida antarctica lipase B-Catalyzed transesterification: new synthetic routes to copolyesters, J Am Chem Soc, 122, 11767, 10.1021/ja002915j Zhong, 2000, Controlled ring-opening polymerization of ω-pentadecalactone with yttrium isopropoxide as an initiator, Macromol Chem Phys, 201, 1329, 10.1002/1521-3935(20000801)201:12<1329::AID-MACP1329>3.0.CO;2-8 Slivniak, 2005, Macrolactones and polyesters from ricinoleic acid, Biomacromolecules, 6, 1679, 10.1021/bm049194r Wang, 2005, Ring-opening polymerization of cyclic monomers with aluminum triflate, Macromol Symp, 224, 193, 10.1002/masy.200550617 Nakayama, 2011, High activity of rare earth tetrahydroborates for ring-opening polymerization of ω-pentadecalactone, J Appl Polym Sci, 121, 2098, 10.1002/app.33834 Kumar, 2001, Copolymerizations of ω-Pentadecalactone and trimethylene carbonate by chemical and lipase catalysis, Macromolecules, 34, 3527, 10.1021/ma0100246 Wilson, 2014, ’Immortal’ ring-opening polymerization of ω-pentadecalactone by Mg (BHT)2(THF)2, Polym Chem, 5, 2691, 10.1039/C4PY00034J Wilson, 2015, Synthesis of ω-Pentadecalactone copolymers with independently tunable thermal and degradation behavior, Macromolecules, 48, 950, 10.1021/ma5022049 Wilson, 2015, Synthesis and postpolymerization modification of one-pot ω-Pentadecalactone block-like copolymers, Biomacromolecules, 16, 3191, 10.1021/acs.biomac.5b00862 Wilson, 2016, Dependence of copolymer sequencing based on lactone ring size and ε-Substitution, ACS Macro Lett, 5, 346, 10.1021/acsmacrolett.5b00940 Nifant’ev, 2016, Monomeric and dimeric magnesium mono-BHT complexes as effective ROP catalysts, Catal Commun, 87, 106, 10.1016/j.catcom.2016.09.018 Bouyahyi, 2014, Metal-based catalysts for controlled ring-opening polymerization of macrolactones: high molecular weight and well-defined copolymer architectures, Macromolecules, 47, 517, 10.1021/ma402072t Jasinska-Walc, 2015, Synthetic principles determining local organization of copolyesters prepared from Lactones and macrolactones, Macromolecules, 48, 502, 10.1021/ma502262e van der Meulen, 2011, Catalytic ring-opening polymerization of renewable macrolactones to high molecular weight polyethylene-like polymers, Macromolecules, 44, 4301, 10.1021/ma200685u Pepels, 2013, Kinetic investigation on the catalytic ring-opening (Co)Polymerization of (Macro)lactones using aluminum salen catalysts, Macromolecules, 46, 4324, 10.1021/ma400731c Pepels, 2015, Mimicking (Linear) low-density polyethylenes using modified polymacrolactones, Macromolecules, 48, 4779, 10.1021/acs.macromol.5b00820 Pepels, 2015, Influence of the main-chain configuration on the mechanical properties of linear aliphatic polyesters, Macromolecules, 48, 5845, 10.1021/acs.macromol.5b01089 Pepels, 2015, Block copolymers of "PE-Like" Poly(pentadecalactone) and Poly(L-lactide): synthesis, properties, and compatibilization of polyethylene/Poly(L-lactide) blends, Macromolecules, 48, 6909, 10.1021/acs.macromol.5b01620 Pepels, 2016, Molecular structure–catalytic activity relationship in the ring-opening polymerization of (Macro)lactones, Macromolecules, 49, 796, 10.1021/acs.macromol.5b02391 Rutkowski, 2017, Toward polyethylene-polyester block and graft copolymers with tunable polarity, Macromolecules, 50, 107, 10.1021/acs.macromol.6b02341 Fuoco, 2015, Ring-opening polymerization of ω-6-hexadecenlactone by a salicylaldiminato aluminum complex: a route to semicrystalline and functional poly(ester)s, Polym Chem, 6, 1727, 10.1039/C4PY01445F Hori, 1999, Ring-opening copolymerization of (R)-β-butyrolactone with macrolide: a new series of poly(hydroxyalkanoate)s, Macromolecules, 32, 3537, 10.1021/ma981846e Zotzmann, 2010, Copolymer networks based on Poly(ω-pentadecalactone) and Poly(ε-caprolactone)Segments as a Versatile Triple-Shape Polymer System, Adv Funct Mater, 20, 3583, 10.1002/adfm.201000478 Zotzmann, 2010, Reversible triple-shape effect of polymer networks containing polypentadecalactone- and poly(ε-caprolactone)-Segments, Adv Mater, 22, 3424, 10.1002/adma.200904202 Zotzmann, 2011, Upscaling the synthesis of biodegradable multiblock copolymers capable of a shape-memory effect, J Mater Sci Mater Med, 22, 2147, 10.1007/s10856-011-4404-6 Behl, 2011, One-way and reversible dual-shape effect of polymer networks based on polypentadecalactone segments, J Artif Organs, 34, 231, 10.5301/IJAO.2011.6424 Balk, 2012, Shape-memory hydrogels with switching segments based on oligo(ω-pentadecalactone), Macromol Mater Eng, 297, 1184, 10.1002/mame.201200232 Kratz, 2012, Temperature-memory effect of copolyesterurethanes and their application potential in minimally invasive medical technologies, Adv Funct Mater, 22, 3057, 10.1002/adfm.201200211 Razzaq, 2012, Oligo(ω-pentadecalactone) decorated magnetic nanoparticles, J Mater Chem, 22, 9237, 10.1039/c2jm16146j Matsumoto, 2012, Shape-memory properties of electrospun non-woven fabrics prepared from degradable polyesterurethanes containing poly(ω-pentadecalactone) hard segments, Eur Polym J, 48, 1866, 10.1016/j.eurpolymj.2012.07.008 Razzaq, 2013, Multifunctional hybrid nanocomposites with magnetically controlled reversible shape–memory effect, Adv Mater, 25, 5730, 10.1002/adma.201302485 Razzaq, 2014, Magnetically controlled shape-memory effects of hybrid nanocomposites from oligo(ω-pentadecalactone) and covalently integrated magnetite nanoparticles, Polymer, 55, 5953, 10.1016/j.polymer.2014.07.025 Schone, 2014, Characterization of langmuir films prepared from copolyesterurethanes based on oligo(ω-pentadecalactone) and oligo(ε-caprolactone) segments, Macromol Chem Phys, 215, 2437, 10.1002/macp.201400377 Wischke, 2014, Method for preparation, programming, and characterization of miniaturized particulate shape-memory polymer matrices, Langmuir, 30, 2820, 10.1021/la4025926 Wang, 2015, Characterization of bi-layered magnetic nanoparticles synthesized via two-step surface-initiated ring-opening polymerization, Pure Appl Chem, 87, 1085, 10.1515/pac-2015-0607 Fang, 2016, Programming structural functions in phase-segregated polymers by implementing a defined thermomechanical history, Polymer, 102, 54, 10.1016/j.polymer.2016.08.105 Schone, 2016, The relevance of hydrophobic segments in multiblock copolyesterurethanes for their enzymatic degradation at the air-water interface, Polymer, 102, 92, 10.1016/j.polymer.2016.09.001 Fernández, 2015, Synthesis and characterization of ω-pentadecalactone-co-ε-decalactone copolymers: evaluation of thermal, mechanical and biodegradation properties, Polymer, 81, 12, 10.1016/j.polymer.2015.11.001 Fernandez, 2016, Synthesis and properties of ω-pentadecalactone-co-δ-hexalactone copolymers: a biodegradable thermoplastic elastomer as an alternative to poly(ε-caprolactone), RSC Adv, 6, 3137, 10.1039/C5RA23404B Fernandez, 2016, Ethylene brassylate-co-δ-hexalactone biobased polymers for application in the medical field: synthesis, characterization and cell culture studies, RSC Adv, 6, 22121, 10.1039/C6RA01065B Fernandez, 2016, Effect of molecular weight on the physical properties of poly(ethylene brassylate) homopolymers, J Mech Behav Biomed Mater, 64, 209, 10.1016/j.jmbbm.2016.07.031 Jin, 2018, Copolymerization of ethylene brassylate with δ-valerolactone towards isodimorphic random copolyesters with continuously tunable mechanical properties, Eur Polym J, 102, 90, 10.1016/j.eurpolymj.2018.03.018 Fernandez, 2017, Ethylene brassylate: searching for new comonomers that enhance the ductility and biodegradability of polylactides, Polym Degrad Stabil, 137, 23, 10.1016/j.polymdegradstab.2017.01.001 Jasinska-Walc, 2014, Topological behavior mimicking ethylene - hexene copolymers using branched lactones and macrolactones, Polym Chem, 5, 3306, 10.1039/C3PY01754K Chang, 2015, Synthesis and characterization of poly(ω-pentadecalactone) for its industrial-scale production, Chem Res Chin Univ, 31, 640, 10.1007/s40242-015-5092-4 Myers, 2017, Ring opening polymerization of macrolactones: high conversions and activities using an yttrium catalyst, Polym Chem, 8, 5780, 10.1039/C7PY00985B Guillaume, 2012, Recent advances in metallo/organo-catalyzed immortal ring-opening polymerization of cyclic carbonates, Catal Sci Technol, 2, 898, 10.1039/c2cy00507g Asano, 1985, ’Immortal’ polymerization. Polymerization of epoxide catalysed by an aluminium porphyrin-alcohol system, J Chem SocChem Commun, 1148, 10.1039/C39850001148 Endo, 1987, Immortal polymerization of ε-caprolactone initiated by aluminum porphyrin in the presence of alcohol, Macromolecules, 20, 2982, 10.1021/ma00178a005 Dove, 2012, Organic catalysis for ring-opening polymerization, ACS Macro Lett, 1, 1409, 10.1021/mz3005956 Nederberg, 2001, New paradigms for organic catalysts: the first organocatalytic living polymerization, Angew Chem Int Ed, 40, 2712, 10.1002/1521-3773(20010716)40:14<2712::AID-ANIE2712>3.0.CO;2-Z Pascual, 2014, Organocatalyzed synthesis of aliphatic polyesters from ethylene brassy late: a cheap and renewable macrolactone, ACS Macro Lett, 3, 849, 10.1021/mz500401u Kamber, 2007, Organocatalytic ring-opening polymerization, Chem Rev, 107, 5813, 10.1021/cr068415b Todd, 2015, Poly(ω-pentadecalactone)-b-poly(l-lactide) block copolymers via organic-catalyzed ring opening polymerization and potential applications, ACS Macro Lett, 4, 408, 10.1021/acsmacrolett.5b00021 Bouyahyi, 2012, Ω-pentandecalactone polymerization and ω-Pentadecalactone/ε-Caprolactone copolymerization reactions using organic catalysts, Macromolecules, 45, 3356, 10.1021/ma3001675 Ladelta, 2017, Ring-opening polymerization of ω-pentadecalactone catalyzed by phosphazene superbases, Polym Chem, 8, 511, 10.1039/C6PY01983H Naumann, 2016, Highly polarized Alkenes as organocatalysts for the polymerization of lactones and trimethylene carbonate, ACS Macro Lett, 5, 134, 10.1021/acsmacrolett.5b00873 Naumann, 2015, Dual catalysis for selective ring-opening polymerization of lactones: evolution toward simplicity, J Am Chem Soc, 137, 14439, 10.1021/jacs.5b09502 Walther, 2017, N-heterocyclic olefin-based (Co)polymerization of a challenging monomer: homopolymerization of ω-Pentadecalactone and its Copolymers with γ-Butyrolactone, δ-Valerolactone, and ε-Caprolactone, Macromolecules, 50, 8406, 10.1021/acs.macromol.7b01678 Wang, 2018, Ring-opening polymerization with lewis pairs and subsequent nucleophilic substitution: a promising strategy to well-defined polyethylene-like polyesters without transesterification, Macromolecules, 51, 836, 10.1021/acs.macromol.7b02378 Pascual, 2013, Acid catalyzed polymerization of macrolactones in bulk and aqueous miniemulsion: ring opening vs. condensation, Eur Polym J, 49, 1601, 10.1016/j.eurpolymj.2013.02.009 Barrère, 2003, Polyester synthesis in aqueous miniemulsion, Polymer, 44, 2833, 10.1016/S0032-3861(03)00151-4 Delgove, 2017, Increasing the solubility range of polyesters by tuning their microstructure with comonomers, Polym Chem, 8, 4696, 10.1039/C7PY00976C Ladelta, 2018, Block copolymers of Macrolactones/Small lactones by a “Catalyst-Switch” organocatalytic strategy. Thermal properties and phase behavior, Macromolecules, 51, 2428, 10.1021/acs.macromol.8b00153 Ravichandran, 2012, Advances in polymeric systems for tissue engineering and biomedical applications, Macromol Biosci, 12, 286, 10.1002/mabi.201100325 Sokolsky-Papkov, 2007, Polymer carriers for drug delivery in tissue engineering, Adv Drug Delivery Rev, 59, 187, 10.1016/j.addr.2007.04.001 Saralidze, 2010, Polymeric microspheres for medical applications, Materials, 3, 3537, 10.3390/ma3063537 Plikk, 2009, Design of resorbable porous tubular copolyester scaffolds for use in nerve regeneration, Biomacromolecules, 10, 1259, 10.1021/bm900093r Jain, 1998, Controlled drug delivery by biodegradable poly(Ester) devices: different preparative approaches, Drug Dev Ind Pharm, 24, 703, 10.3109/03639049809082719 Jiao, 2007, Surface modification of polyester biomaterials for tissue engineering, Biomed Mater, 2, R24, 10.1088/1748-6041/2/4/R02 Goddard, 2007, Polymer surface modification for the attachment of bioactive compounds, Prog Polym Sci, 32, 698, 10.1016/j.progpolymsci.2007.04.002 Uyama, 1998, Enzymatic synthesis of terminal-functionalized polyesters by initiator method, Acta Polym Sin, 49, 700, 10.1002/(SICI)1521-4044(199812)49:12<700::AID-APOL700>3.0.CO;2-C Descour, 2015, In situ compatibilization of alkenyl-terminated polymer blends using cross metathesis, RSC Adv, 5, 9658, 10.1039/C4RA11056K Kalra, 2004, Chemoenzymatic synthesis of new brush copolymers comprising poly(ω-pentadecalactone) with unusual thermal and crystalline properties, Macromolecules, 37, 1243, 10.1021/ma035083t Takwa, 2008, Lipase catalyzed HEMA initiated ring-opening polymerization: in situ formation of mixed polyester methacrylates by transesterification, Biomacromolecules, 9, 704, 10.1021/bm7010449 Xiao, 2009, Systematic comparison of HEA and HEMA as initiators in enzymatic ring-opening polymerizations, Macromol Biosci, 9, 713, 10.1002/mabi.200800290 Uyama, 1995, One-shot synthesis of polyester macromonomer by enzymatic ring-opening polymerization of lactone in the presence of vinyl ester, Chem Lett, 1047, 10.1246/cl.1995.1047 Uyama, 1997, Single-step acylation of polyester terminals by enzymatic ring-opening polymerization of 12-dodecanolide in the presence of acyclic vinyl esters, Bull Chem Soc Jpn, 70, 1691, 10.1246/bcsj.70.1691 Korzhikov, 2013, Enzyme-mediated ring-opening polymerization of Pentadecalactone to obtain biodegradable polymer for fabrication of scaffolds for bone tissue engineering, Int J Polym Sci, 2013, 10.1155/2013/476748 Takwa, 2006, One-pot difunctionalization of poly(ω-pentadecalactone) with thiol-Thiol or thiol-acrylate groups, Catalyzed by Candida antarctica Lipase B, Macromol Rapid Commun, 27, 1932, 10.1002/marc.200600527 Takwa, 2008, Single-step, solvent-free enzymatic route to α,ω-functionalized polypentadecalactone macromonomers, Macromolecules, 41, 5230, 10.1021/ma800074a Simpson, 2008, Thiol-functionalized poly(ω-pentadecalactone) telechelics for semicrystalline polymer networks, Macromolecules, 41, 3613, 10.1021/ma702419m Kumar, 2002, Recognition by lipases of ω-Hydroxyl macroinitiators for diblock copolymer synthesis, Macromolecules, 35, 7606, 10.1021/ma020060k Chen, 2015, Amphiphilic poly(ethylene glycol)-b-poly(ethylene brassylate) copolymers: one-pot synthesis, self-assembly, and controlled drug release, Chin Chem Lett, 26, 1319, 10.1016/j.cclet.2015.05.050 Bansal, 2015, New biomaterials from renewable resources - amphiphilic block copolymers from δ-decalactone, Polym Chem, 6, 7196, 10.1039/C5PY01203A Bansal, 2018, Renewable poly(δ-decalactone) based block copolymer micelles as drug delivery vehicle: in vitro and in vivo evaluation, Saudi Pharm J, 26, 358, 10.1016/j.jsps.2018.01.006 Pflughaupt, 2016, Synthesis of poly(ω-pentadecalactone)-b-poly(acrylate) diblock copolymers via a combination of enzymatic ring-opening and RAFT polymerization techniques, J Polym SciPart A Polym Chem, 54, 3326, 10.1002/pola.28221 Chen, 2016, Synthesis and self-assembly of four-armed star copolymer based on poly(ethylene brassylate) hydrophobic block as potential drug carries, J Nanopart Res, 18, 10.1007/s11051-016-3446-6 Arnebold, 2016, Fast switchable, epoxy based shape-memory polymers with high strength and toughness, Polymer, 83, 40, 10.1016/j.polymer.2015.12.007 Pilate, 2018, Poly(ε-caprolactone) and poly(ω-pentadecalactone)-Based networks with two-way shape-memory effect through 2+2 cycloaddition reactions, Macromol Chem Phys, 219 Jérôme, 2008, Recent advances in the synthesis of aliphatic polyesters by ring-opening polymerization, Adv Drug Deliv Rev, 60, 1056, 10.1016/j.addr.2008.02.008 Vaida, 2011, Tailor-made polyesters based on pentadecalactone via enzymatic catalysis, Green Chem, 13, 889, 10.1039/c1gc15044h van der Meulen, 2008, Polymers from functional macrolactones as potential biomaterials: enzymatic ring opening polymerization, biodegradation, and biocompatibility, Biomacromolecules, 9, 3404, 10.1021/bm800898c van der Meulen, 2011, Copolymers from unsaturated macrolactones: toward the design of cross-linked biodegradable polyesters, Biomacromolecules, 12, 837, 10.1021/bm200084y Van Der Mee, 2006, Oxo-crown-ethers as comonomers for tuning polyester properties, J Polym SciPart A Polym Chem, 44, 2166, 10.1002/pola.21329 Illy, 2013, Synthesis and anionic ring-opening polymerization of crown-ether-like macrocyclic dilactones: an alternative route to peg-containing polyesters PEG-containing polyesters and related networks, Eur Polym J, 49, 4087, 10.1016/j.eurpolymj.2013.09.014 Manzini, 2010, Entropically-driven ring-opening polymerization of macrocyclic esters with up to 84-membered rings catalysed by polymer-supported Candida antarctica lipase B, Polym Chem, 1, 339, 10.1039/B9PY00350A Jiang, 2007, Lipase-catalyzed copolymerization of ω-pentadecalactone with p-dioxanone and characterization of copolymer thermal and crystalline properties, Biomacromolecules, 8, 2262, 10.1021/bm070138a Liu, 2011, Biodegradation, biocompatibility, and drug delivery in poly(ω-pentadecalactone-co-p-dioxanone) copolyesters, Biomaterials, 32, 6646, 10.1016/j.biomaterials.2011.05.046 Magusin, 2005, Novel biodegradable poly(pentadecalactone-co-oxo-crown ether) studied with solid-state 1H and 13C NMR, Macromol Symp, 230, 126, 10.1002/masy.200551151 Pepels, 2016, Catalytic ring-opening (Co)polymerization of semiaromatic and aliphatic (Macro)lactones, Macromolecules, 49, 4441, 10.1021/acs.macromol.6b00744 Wisse, 2007, Poly(caprolactone-co-oxo-crown ether)-based poly(urethane)urea for soft tissue engineering applications, Biomacromolecules, 8, 2739, 10.1021/bm070375d Focarete, 2002, Copolymers of ω-Pentadecalactone and trimethylene carbonate from lipase catalysis: influence of microstructure on solid-state properties, Macromolecules, 35, 8066, 10.1021/ma0205966 Veld, 2007, Selective polymerization of functional monomers with novozym 435, J Polym Sci Part A Polym Chem, 45, 5968, 10.1002/pola.22350 Uyama, 2001, Chemoselective ring-opening polymerization of a lactone having exo-methylene group with lipase catalysis, Macromolecules, 34, 6554, 10.1021/ma010893v Habaue, 2003, Chemospecific ring-opening polymerization of α-methylenemacrolides, Polymer, 44, 5195, 10.1016/S0032-3861(03)00491-9 Habaue, 2002, Stereospecific anionic polymerization of α-(alkoxymethyl)acrylate derivatives affording novel vinyl polymers with macrocyclic side chains, Polymer, 43, 3469, 10.1016/S0032-3861(02)00045-9 Habaue, 2002, Anionic polymerization of macrocyclic α-(alkoxymethyl)acrylates leading to novel vinyl polymer with crown ether type side chain, Macromolecules, 35, 2432, 10.1021/ma0116452 Ates, 2011, Side-chain functionalization of unsaturated polyesters from ring-opening polymerization of macrolactones by thiol-ene click chemistry, Polym Chem, 2, 309, 10.1039/C0PY00294A Ates, 2014, Functional films from unsaturated poly(macrolactones) by thiol-ene cross-linking and functionalization, Polym Chem, 5, 2936, 10.1039/c3py01679j Ates, 2014, Functional brush-decorated poly(globalide) films by ARGET-ATRP for bioconjugation, Macromol Biosci, 14, 1600, 10.1002/mabi.201400282 de Oliveira, 2017, Direct UV-Triggered thiol–ene cross-linking of electrospun polyester fibers from unsaturated poly(macrolactone)s and their drug loading by solvent swelling, Biomacromolecules, 18, 4292, 10.1021/acs.biomac.7b01335 Claudino, 2012, Photoinduced thiol-ene crosslinking of globalide/ε-caprolactone copolymers: curing performance and resulting thermoset properties, J Polym Sci Part A Polym Chem, 50, 16, 10.1002/pola.24940 Wang, 2017, Two-way reversible shape memory polymers made of cross-linked cocrystallizable random copolymers with tunable actuation temperatures, Macromolecules, 50, 8570, 10.1021/acs.macromol.7b01815 Yu, 2012, Lipase/esterase-catalyzed synthesis of aliphatic polyesters via polycondensation: a review, Process Biochem, 47, 1027, 10.1016/j.procbio.2012.04.006 Namekawa, 2000, Enzymatic synthesis of polyesters from Lactones, dicarboxylic acid divinyl esters, and glycols through combination of ring-opening polymerization and polycondensation, Biomacromolecules, 1, 335, 10.1021/bm000030u Thompson, 2007, Evaluation of ibuprofen-loaded microspheres prepared from novel copolyesters, Int J Pharm, 329, 53, 10.1016/j.ijpharm.2006.08.019 Gaskell, 2008, Encapsulation and release of α-chymotrypsin from poly(glycerol adipate-co-ω-pentadecalactone) microparticles, J Microencapsulation, 25, 187, 10.1080/02652040701848775 Thompson, 2008, Synthesis and evaluation of novel polyester-ibuprofen conjugates for modified drug release, Drug Dev Ind Pharm, 34, 877, 10.1080/03639040801929075 Thompson, 2009, Preparation and evaluation of microspheres prepared from novel polyester-ibuprofen conjugates blended with non-conjugated ibuprofen, J Microencapsulation, 26, 676, 10.3109/02652040802656333 Tawfeek, 2011, Poly(Glycerol Adipate-co-ω-Pentadecalactone) spray-dried microparticles as sustained release carriers for pulmonary delivery, Pharm Res, 28, 2086, 10.1007/s11095-011-0433-6 Jan, 2013, Synthesis, conjugation and evaluation of some novel polymers and their micro particles for sustained release drug formulations, Pak J Pharm Sci, 26, 741 Tawfeek, 2014, Evaluation of biodegradable polyester-co-lactone microparticles for protein delivery, Drug Dev Ind Pharm, 40, 1213, 10.3109/03639045.2013.814060 Alfagih, 2015, Pulmonary delivery of proteins using nanocomposite microcarriers, J Pharm Sci, 104, 4386, 10.1002/jps.24681 Kunda, 2015, Bovine serum albumin adsorbed PGA-co-PDL nanocarriers for vaccine delivery via dry powder inhalation, Pharm Res, 32, 1341, 10.1007/s11095-014-1538-5 Tawfeek, 2017, Colonic delivery of indometacin loaded PGA-co-PDL microparticles coated with Eudragit L100-55 from fast disintegrating tablets, Int J Pharm, 531, 80, 10.1016/j.ijpharm.2017.08.069 Rodrigues, 2018, Mucosal immunization with PspA (Pneumococcal surface protein A)-adsorbed nanoparticles targeting the lungs for protection against pneumococcal infection, PLoS One, 13, 10.1371/journal.pone.0191692 Tawfeek, 2013, Dry powder inhalation of macromolecules using novel PEG-co-polyester microparticle carriers, Int J Pharm, 441, 611, 10.1016/j.ijpharm.2012.10.036 Tawfeek, 2013, Evaluation of PEG and mPEG-co-(PGA-co-PDL) microparticles loaded with sodium diclofenac, Saudi Pharm J, 21, 387, 10.1016/j.jsps.2012.11.006 Jiang, 2008, Lipase-catalyzed synthesis of aliphatic polyesters via copolymerization of lactone, dialkyl diester, and diol, Biomacromolecules, 9, 3246, 10.1021/bm800814m Mazzocchetti, 2009, Enzymatic synthesis and structural and thermal properties of poly(ω-pentadecalactone-co-butylene-co-succinate), Macromolecules, 42, 7811, 10.1021/ma901338v Liu, 2009, Poly(ω-pentadecalactone-co-butylene-co-succinate) nanoparticles as biodegradable carriers for camptothecin delivery, Biomaterials, 30, 5707, 10.1016/j.biomaterials.2009.06.061 Mazzocchetti, 2011, Copolymers of ethyl glycolate and ω–pentadecalactone: enzymatic synthesis and solid-state characterization, Eur Polym J, 47, 942, 10.1016/j.eurpolymj.2011.01.003 Voevodina, 2014, Exploring the solid state properties of enzymatic poly(amine-co-ester) terpolymers to expand their applications in gene transfection, RSC Adv, 4, 8953, 10.1039/c3ra46918b Zhou, 2011, Biodegradable poly(amine-co-ester) terpolymers for targeted gene delivery, Nat Mater, 11, 82, 10.1038/nmat3187 Liu, 2015, Enzymatic synthesis of poly(ω-pentadecalactone-co-butylene-co-3,3’ -dithiodipropionate) copolyesters and self-assembly of the PEGylated copolymer micelles as redox-responsive nanocarriers for doxorubicin delivery, Polym Chem, 6, 1997, 10.1039/C4PY01321B Jiang, 2011, Lipase-Catalyzed Copolymerization of Dialkyl Carbonate with 1,4-Butanediol and ω-Pentadecalactone: Synthesis of Poly(ω-pentadecalactone-co-butylene-co-carbonate), Biomacromolecules, 12, 1912, 10.1021/bm2002522 Mazzocchetti, 2012, Random copolymerization with a large lactone enhances aliphatic polycarbonate crystallinity, Eur Polym J, 48, 1883, 10.1016/j.eurpolymj.2012.08.010 Martino, 2012, Enzymatic synthesis, thermal and crystalline properties of a poly(β–amino ester) and poly(lactone-co-β–amino ester) copolymers, Polymer, 53, 1839, 10.1016/j.polymer.2012.03.005 Hua, 2018, Exploiting ring-opening aminolysis-condensation as a polymerization pathway to structurally diverse biobased polyamides, Biomacromolecules, 19, 1573, 10.1021/acs.biomac.8b00322 Zhang, 2014, Micelles of enzymatically synthesized PEG-poly(amine-co-ester) block copolymers as pH-responsive nanocarriers for docetaxel delivery, Colloids Surf B, 115, 349, 10.1016/j.colsurfb.2013.12.029 Zhang, 2014, PEGylated poly(amine-co-ester) micelles as biodegradable non-viral gene vectors with enhanced stability, reduced toxicity and higher in vivo transfection efficacy, J Mater Chem B, 2, 4034, 10.1039/c4tb00439f Chen, 2017, Enzymatic PEG-Poly(amine-co-disulfide ester) nanoparticles as pH-and redox-responsive drug nanocarriers for efficient antitumor treatment, ACS Appl Mater Interfaces, 9, 30519, 10.1021/acsami.7b10148 Chen, 2016, Enzymatic PEGylated poly(lactone-co-β-amino ester) nanoparticles as biodegradable, biocompatible and stable vectors for gene delivery, ACS Appl Mater Interfaces, 8, 490, 10.1021/acsami.5b09437 Eriksson, 2009, Enzymatic One-Pot Route to Telechelic Polypentadecalactone Epoxide: Synthesis, UV Curing, and Characterization, Biomacromolecules, 10, 3108, 10.1021/bm9007925 Seyednejad, 2011, Functional aliphatic polyesters for biomedical and pharmaceutical applications, J Control Release, 152, 168, 10.1016/j.jconrel.2010.12.016 Amass, 1998, A review of biodegradable polymers: uses, current developments in the synthesis and characterization of biodegradable polyesters, blends of biodegradable polymers and recent advances in biodegradation studies, Polym Int, 47, 89, 10.1002/(SICI)1097-0126(1998100)47:2<89::AID-PI86>3.0.CO;2-F Vert, 2005, Aliphatic polyesters: great degradable polymers that cannot do everything, Biomacromolecules, 6, 538, 10.1021/bm0494702 Gazzano, 2003, Crystal structure of poly(ω-pentadecalactone), J Polym Sci Part B Polym Phys, 41, 1009, 10.1002/polb.10419 Cai, 2009, Polypentadecalactone prepared by lipase catalysis: crystallization kinetics and morphology, Polym Int, 58, 944, 10.1002/pi.2624 de Geus, 2010, Performance polymers from renewable monomers: high molecular weight poly(pentadecalactone) for fiber applications, Polym Chem, 1, 525, 10.1039/b9py00360f Cai, 2011, Real-time structure changes during uniaxial stretching of poly (ω-pentadecalactone) by in situ synchrotron WAXD/SAXS techniques, Macromolecules, 44, 3874, 10.1021/ma102949h Jeremic, 2014 Wilsens, 2016, Improving stiffness, strength, and toughness of poly(ω-pentadecalactone) fibers through in situ reinforcement with a vanillic acid-based thermotropic liquid crystalline Polyester, Macromolecules, 49, 2228, 10.1021/acs.macromol.5b02419 Ye, 2017, Supernucleating role of poly(ω-pentadecalactone) during the crystallization of poly(ε-caprolactone) composites, Ind Eng Chem Res, 56, 13725, 10.1021/acs.iecr.7b03322 Ulery, 2011, Biomedical applications of biodegradable polymers, J Polym Sci Part B Polym Phys, 49, 832, 10.1002/polb.22259 Azevedo, 2005, Understanding the enzymatic degradation of biodegradable polymers and strategies to control their degradation rate, 177 Ceccorulli, 2005, Cocrystallization of random copolymers of ω-pentadecalactone and ε-caprolactone synthesized by lipase catalysis, Biomacromolecules, 6, 902, 10.1021/bm0493279 Focarete, 2010, Electrospun scaffolds of a polyhydroxyalkanoate consisting of ω-Hydroxylpentadecanoate repeat units: fabrication and in vitro biocompatibility studies, J Biomater SciPolym Ed, 21, 1283, 10.1163/092050609X12517190417597 Ziemba, 2018, Poly-l-lactic acid-co-poly(pentadecalactone) electrospun fibers result in greater neurite outgrowth of chick dorsal root ganglia in vitro compared to Poly-L-lactic acid fibers, ACS Biomater Sci Eng, 4, 1491 Albertsson, 2002, Aliphatic polyesters: synthesis, properties and applications. Degradable aliphatic polyesters, Adv Polym Sci, 157, 1, 10.1007/3-540-45734-8_1