Supramolecular System Obtained by Adamantyl-Containing Pnipam Copolymers with Cyclodextrin Dimers

doi:10.7517/j.issn.1674-0475.2012.03.200

Abstract

Abstract: The adamantyl-containing polymer (Pnipam-Ad) and cyclodextrin dimer (trans-Azo β-CD Dimer) were synthesized. A supramolecular system was constructed by the formation of inclusion complex between Pnipam-Ad and trans-Azo β-CD Dimer. The inclusion behavior was investigated by 2D NMR and viscosity measurement. The interaction between Pnipam-Ad and trans-Azo β-CD Dimer was depended on the concentration of Pnipam-Ad, trans-Azo β-CD Dimer and the photoisomerization of trans-Azo β-CD Dimer. In addition, the lower critical solution temperature (LCST) of the supramolecular networks consisting trans-Azo β-CD Dimer and Pnipam-Ad are significantly lower than those of pure P(NIPAM).

Key words: cyclodextrin dimer, host-guest interaction, thermo-sensitivity, supramolecular

CLC Number:

LI Shu-jing, LIANG Hai-yan, WANG Xin-rui. Supramolecular System Obtained by Adamantyl-Containing Pnipam Copolymers with Cyclodextrin Dimers[J]. Imaging Science and Photochemistry, 2012, 30(3): 200-209.

References

[1] Connors K A. The stability of cyclodextrin complexes in solution[J]. Chem. Rev., 1997, 97(5): 1325-1358.
[2] Li S, Purdy W C. Cyclodextrins and their applications in analytical chemistry[J]. Chem. Rev., 1992, 92(6): 1457-1470.
[3] Li J, Yang C, Li H Z, et al. Cationic supramolecules composed of multiple oligoethylenimine-grafted β-cyclodextrins threaded on a polymer chain for efficient gene delivery[J]. Adv. Mater., 2006, 18(22): 2969-2974.
[4] Fujita H, Ooya T, Kurisawa M,et al. Thermally switchable polyrotaxane as a model of stimuli-responsive supramolecules for nano-scale devices[J]. Macromol. Rapid Commun., 1996, 17(171): 509-515.
[5] Ooya T, Yui N. Multivalent interactions between biotin-polyrotaxane conjugates and streptavidin as a model of new targeting for transporters[J]. J. Control. Rel., 2002, 80(1/3): 219-228.
[6] Guo M, Jiang M, Pispas S, et al. Supramolecular hydrogels made of end-functionalized low-molecular-weight PEG and α-cyclodextrin and their hybridization with SiO₂ nanoparticles through host-guest interaction[J]. Macromolecules, 2008, 41(24): 9744-9749.
[7] Zhao S P, Lee J H, Xu W J. Supramolecular hydrogels formed from biodegradable ternary COS-g-PCL-b-MPEG copolymer with α-cyclodextrin and their drug release[J]. Carbohyd. Res., 2009, 344(16): 2201-2208.
[8] Li J, Loh X J. Cyclodextrin-based supramolecular architectures: synthesis, structures, and applications for drug and gene delivery[J]. Adv. Drug Del. Rev., 2008, 60: 1000-1017.
[9] Wu D Q, Wang T, Lu B, et al. Fabrication of supramolecular hydrogels for drug delivery and stem cell encapsulation[J]. Langmuir, 2008, 24: 10306-10312.
[10] Ichi T, Watanabe J, Ooya T, et al. Controllable erosion time and profile in poly(ethylene glycol) hydrogels by supramolecular structure of hydrolyzable polyrotaxane[J]. Biomacromolecules, 2001, 2: 204-210.
[11] Gosselet N M, Beucler F, Renard E, et al. Association of hydrophobically modified poly (N,N-dimethylacrylamide hydroxyethylmethacrylate) with water soluble β-cyclodextrin polymers[J]. Colloids Surfaces A: Physico Chem. Eng. Aspects, 1999, 155(2-3): 177-188.
[12] Sandier A, Brown W, Mays H, Interaction between an adamantane end-capped poly(ethylene oxide) and a β-cyclodextrin polymer[J]. Langmuir, 2000, 16(4): 1634-1642.
[13] Kretschmann O, Choi S W, Ritter H, et al. Switchable hydrogels obtained by supramolecular cross-linking of adamantyl-containing LCST copolymers with cyclodextrin dimers[J]. Angew. Chem. Int. Ed., 2006, 45(26): 4361-4365.
[14] Chen G S, Jiang M. Cyclodextrin-based inclusion complexation bridging supramolecular chemistry and macromolecular self-assembly[J]. Chem. Soc. Rev., 2011, 40: 2254-2266.
[15] Koppmans C,Ritter H. Formation of physical hydrogels via host-guest interactions of β-cyclodextrin polymers and copolymers bearing adamantyl groups[J]. Macromolecules, 2008, 41(20): 7418-7422.
[16] Auzely-Velty R, Rinaudo M. New supramolecular assemblies of a cyclodextrin-grafted chitosan through specitific complexation[J]. Macromolecules, 2002, 35(21): 7955-7962.
[17] Zhong N, Byun H S, Bittman R. An improved synthesis of 6-O-monotosyl-6-deoxy-β-cyclodextrin[J]. Tetrahedr. Lett., 1998, 39(7): 2919-2920.
[18] Melton L D, Slessor K N. Synthesis of monosubstituted cyclohexaamyloses[J]. Carbohyd. Res., 1971, 18(1): 29-37.
[19] Li S J, Taura D, Hshidzume A, Harada A. Light-switchable janus
[2] rotaxanes based on α-cyclodextrin derivatives bearing two recognition sites linked with oligo(ethylene glycol)[J]. Chem.-An Asian J., 2010, 5(10): 2281-2289.
[20] Yamada H, Fujita E, Nishmura S I. High performance polymer supports for enzyme-assisted synthesis of glycoconjugates[J]. Carbohyd. Res., 1998, 305(3-4): 443-461.