Supramolecular Inclusion Complexes of a Star Polymer Containing Cholesterol End-Capped Poly(ε-caprolactone) Arms with β-Cyclodextrin

被引:12
作者
Doganci, Erdinc [1 ,2 ]
Gorur, Mesut [3 ]
Uyanik, Cavit [4 ]
Yilmaz, Faruk [1 ]
机构
[1] Gebze Inst Technol, Dept Chem, TR-41400 Gebze, Kocaeli, Turkey
[2] Kocaeli Univ, Dept Sci Educ, TR-41380 Kocaeli, Turkey
[3] Istanbul Medeniyet Univ, Dept Chem, TR-34720 Istanbul, Turkey
[4] Kocaeli Univ, Dept Chem, TR-41380 Kocaeli, Turkey
关键词
cholesterol; click chemistry; -cyclodextrin; epsilon-caprolactone; inclusion chemistry; inclusion complex; star polymers; supramolecular structures; SELF-ASSEMBLING BIOMATERIALS; ALPHA-CYCLODEXTRIN; POLY(ETHYLENE GLYCOL); BLOCK-COPOLYMERS; FUNCTIONALIZED POLYMER; ALIPHATIC POLYESTERS; BUILDING-BLOCKS; CLICK REACTIONS; GENE DELIVERY; SIDE-GROUPS;
D O I
10.1002/pola.27408
中图分类号
O63 [高分子化学(高聚物)];
学科分类号
070305 ; 080501 ; 081704 ;
摘要
A novel hexa-armed and star-shaped polymer containing cholesterol end-capped poly(epsilon-caprolactone) arms emanating from a phosphazene core (N3P3-(PCL-Chol)(6)) was synthesized by a combination of ring-opening polymerization and click chemistry techniques. For this purpose, the terminal OH groups of the synthesized precursor (N3P3-(PCL-OH)(6)) were converted into -Chol through a series of reaction. Both N3P3-(PCL-OH)(6) and N3P3-(PCL-Chol)(6) were then employed in the preparation of supramolecular inclusion complexes (ICs) with -cyclodextrin (-CD). The latter formed ICs with -CD in higher yield. The host-guest stoichiometry (epsilon-CL:-CD, mol:mol) in the ICs of N3P3-(PCL-Chol)(6) was found to be 1.2. The formation of supramolecular ICs of N3P3-(PCL-Chol)(6) with -CD was confirmed by using Fourier transform infrared (FTIR) and H-1 nuclear magnetic resonance (NMR) spectroscopic methods, wide-angle X-ray diffraction (WAXD), and thermal analysis techniques. WAXD data showed that the obtained ICs with N3P3-(PCL-Chol)(6) had a channel-type crystalline structure, indicating the suppression of the original crystallization of N3P3-(PCL-Chol)(6) in -CD cavities. Moreover, the thermal stabilities of ICs were found to be higher than those of the free star polymer and -CD. Furthermore, the surface properties of N3P3-(PCL-Chol)(6) and its ICs with -CD were investigated by static contact angle measurements. The obtained results proved that the wettability of N3P3-(PCL-Chol)(6) successfully increased with the formation of its ICs with -CD. (c) 2014 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2014, 52, 3406-3420
引用
收藏
页码:3406 / 3420
页数:15
相关论文
共 77 条
[1]   SMALL-MOLECULE PHOSPHAZENE RINGS AS MODELS FOR HIGH POLYMERIC CHAINS [J].
ALLCOCK, HR .
ACCOUNTS OF CHEMICAL RESEARCH, 1979, 12 (10) :351-358
[2]   Organic polymers with cyclophosphazene side groups: Influence of the phosphazene on physical properties and thermolysis [J].
Allcock, HR ;
Hartle, TJ ;
Taylor, JP ;
Sunderland, NJ .
MACROMOLECULES, 2001, 34 (12) :3896-3904
[3]   Patterning poly(organophosphazenes) for selective cell adhesion applications [J].
Barrett, EW ;
Phelps, MVB ;
Silva, RJ ;
Gaumond, RP ;
Allcock, HR .
BIOMACROMOLECULES, 2005, 6 (03) :1689-1697
[4]   New textile applications of cyclodextrins [J].
Buschmann, HJ ;
Knittel, D ;
Schollmeyer, E .
JOURNAL OF INCLUSION PHENOMENA AND MACROCYCLIC CHEMISTRY, 2001, 40 (03) :169-172
[5]   Synthesis, characterization and thermal properties of a novel star polymer consisting of poly(ε-caprolactone) arms emanating from an octa-functional porphyrazine core [J].
Celik, Asuman ;
Kemikli, Nurufe ;
Ozturk, Ramazan ;
Muftuoglu, Ali Ekrem ;
Yilmaz, Faruk .
REACTIVE & FUNCTIONAL POLYMERS, 2009, 69 (09) :705-713
[6]   Synthesis of the organic/inorganic hybrid star polymers and their inclusion complexes with cyclodextrins [J].
Chan, SC ;
Kuo, SW ;
Chang, FC .
MACROMOLECULES, 2005, 38 (08) :3099-3107
[7]   Cyclodextrin-based inclusion complexation bridging supramolecular chemistry and macromolecular self-assembly [J].
Chen, Guosong ;
Jiang, Ming .
CHEMICAL SOCIETY REVIEWS, 2011, 40 (05) :2254-2266
[8]   Novel highly fluorinated perfluorocyclobutane-based phosphazene polymers for photonic applications [J].
Cho, Song Yun ;
Allcock, Harry R. .
CHEMISTRY OF MATERIALS, 2007, 19 (25) :6338-6344
[9]   Supramolecular self-assembly of architecturally variant α-cyclodextrin inclusion complexes as building blocks of hexagonally aligned microfibrils [J].
Chung, Jae Woo ;
Kang, Tae Jin ;
Kwak, Seung-Yeop .
MACROMOLECULES, 2007, 40 (12) :4225-4234
[10]   Supramolecular polypseudorotaxanes composed of star-shaped porphyrin-cored poly(ε-caprolactone) and α-cyclodextrin [J].
Dai, Xiao-Hui ;
Dong, Chang-Ming ;
Fa, Huan-Bao ;
Yan, Deyue ;
Wei, Yen .
BIOMACROMOLECULES, 2006, 7 (12) :3527-3533