Synthesis and properties of block polypseudorotaxanes by threading cucurbit[6]uril

Iranian Polymer Journal (English Edition)

Volumn 21, Issue 11, 2012, Pages 783-792

  Wang, Hong ^a,b   Zhu, Yuejun ^c   Ren, Xiaona ^a,b   Wang, Minggang ^a,b   Tan, Yebang ^a,b  

^a SHANDONG UNIVERSITY   (China)

^b BEIJING UNIVERSITY OF POSTS AND TELECOMMUNICATIONS   (China)

^c CNOOC RESEARCH INSTITUTE   (China)

Author keywords

Block copolymer; Cucurbituril; Polypseudorotaxanes; Self assembly; Water soluble polymer

Indexed keywords

4-VINYLBENZYL; AGGREGATION BEHAVIOR; AVERAGE NUMBERS; CONTROLLED RELEASE; CUCURBIT[6]URIL; CUCURBIT[N]URIL; CUCURBITURILS; DYNAMIC LIGHT SCATTERING MEASUREMENT; FLUORESCENCE INTENSITIES; FLUORESCENCE SPECTROMETRY; HYDRODYNAMIC RADIUS; METHOXYPOLYETHYLENE GLYCOL; MOLECULAR FEATURE; NMR STUDIES; POLYPSEUDOROTAXANES; REPEAT RECOGNITION; SIDE-CHAINS; SOLUTION TEMPERATURE; TEMPERATURE CHANGES; TRANSMISSION ELECTRON MICROSCOPY OBSERVATION; UV-VIS ABSORPTION BANDS; WATER-SOLUBLE BLOCK; WATERSOLUBLE POLYMERS;

ASSOCIATION REACTIONS; BLOCK COPOLYMERS; DRUG DELIVERY; FLUORESCENCE; FLUORESCENCE SPECTROSCOPY; PARAFFINS; SELF ASSEMBLY; TRANSMISSION ELECTRON MICROSCOPY;

POLYETHYLENE GLYCOLS;

EID: 84867804769     PISSN: 10261265     EISSN: 17355265     Source Type: Journal    
DOI: 10.1007/s13726-012-0082-6     Document Type: Article

References (43)

1. Coronado E, Gavina P, Tatay S (2009) Catenanes and threaded systems: from solution to surfaces. Chem Soc Rev 38:1674-1689
2. Thibeault D, Morin J-F (2010) Recent advances in the synthesis of ammonium-based rotaxanes. Molecules 15:3709-3730
3. Niu Z, Gibson HW (2009) Polycatenanes. Chem Rev 109:6024-6046
4. Wenz G, Han BH, Muller A (2006) Cyclodextrin rotaxanes and polyrotaxanes. Chem Rev 106:782-817
5. Schneider H-J, Yatsimirsky AK (2008) Selectivity in supramolecular host-guest complexes. Chem Soc Rev 37:263-277
6. Harada A, Hashidzume A, Yamaguchi H, Takashima Y (2009) Polymeric rotaxanes. Chem Rev 109:5974-6023
7. Lee HK, Park KM, Jeon YJ, Kim D, Oh DH, Kim HS, Park CK, Kim K (2005) Vesicle formed by amphiphilc cucurbit[6]uril: versatile, noncovalent modification of the vesicle surface, and multivalent binding of sugar-decorated vesicles to lectin. J Am Chem Soc 127:5006-5007
8. Saleh N, Koner AL, Nau WM (2008) Activation and stabilization of drugs by supramolecular pKa shifts: drug-delivery applications tailored for cucurbiturils. Angew Chem Int Ed 47:5398-5401
9. Bernardos A, Aznar E, Dolores Marcos M, Martinez-Manez R, Sancenon F, Soto J, Manuel Barat J, Amoros P (2009) Enzymeresponsive controlled release using mesoporous silica supports capped with lactose. Angew Chem Int Ed 48:5884-5887
10. Hennig A, Bakirci H, Nau WM (2007) Label-free continuous enzyme assays with macrocycle-fluorescent dye complexes. Nat Methods 4:629-632
11. Ghale G, Ramalingam V, Urbach AR, Nau WM (2011) Determining protease substrate selectivity and inhibition by label-free supramolecular tandem enzyme assays. J Am Chem Soc 133:7528-7535
12. Wang R, Macartney DH (2008) Cucurbit[7]uril host-guest complexes of the histamine H2-receptor antagonist ranitidine. Org Biomol Chem 6:1955-1960
13. Miyahara Y, Abe K, Inazu T (2002) "Molecular" molecular sieves: lid-free decamethylcucurbit[5]uril absorbs and desorbs gases selectively. Angew Chem Int Ed 41:3020-3023
14. Durola F, Sauvage J-P, Wenger OS (2010) The magic effect of endocyclic but non-sterically hindering biisoquinoline chelates: from fast-moving molecular shuttles to [3]rotaxanes. Coord Chem Rev 254:1748-1759
15. Gassensmith JJ, Baumes JM, Smith BD (2009) Discovery and early development of squaraine rotaxanes. Chem Commun 42:6329-6338
16. Huang F, Gibson HW (2005) Polypseudorotaxanes and polyrotaxanes. Prog Polym Sci 30:982-1018
17. Sauvage J, Dietrich-Buchecker C (1999) Catenanes. Rotaxanes and Knots, VCH, Weilheim
18. Okumura Y, Ito K (2001) The polyrotaxane gel: a topological gel by figure-of-eight cross-links. Adv Mater 13:485-487
19. Ritter H, Sadowski O, Tepper E (2003) Influence of cyclodextrin molecules on the synthesis and the thermoresponsive solution behavior of N-isopropylacrylamide copolymers with adamantyl groups in the side-chains. Angew Chem Int Ed 42:3171-3173
20. Koopmans C, Ritter H (2007) Color change of N-isopropylacrylamide copolymer bearing Reichardts dye as optical sensor for lower critical solution temperature and for host-guest interaction with beta-cyclodextrin. J Am Chem Soc 129:3502-3503
21. Kim K (2002) Mechanically interlocked molecules incorporating cucurbituril and their supramolecular assemblies. Chem Soc Rev 31:96-107
22. Jeon YJ, Bharadwaj PK, Choi SW, Lee JW, Kim K (2002) Supramolecular amphiphiles: spontaneous formation of vesicles triggered by formation of a charge-transfer complex in a host. Angew Chem Int Ed 41:4474-4476
23. Park KM, Roh SG, Lee E, Kim J, Kim HJ, Lee JW, Kim K (2002) Construction of a square-wave-shaped one-dimensional polyrotaxane using a preorganized L-shaped pseudorotaxane. Supramol Chem 14:153-158
24. Jeon WS, Kim E, Ko YH, Hwang IH, Lee JW, Kim SY, Kim HJ, Kim K (2005) Molecular loop lock: a redox-driven molecular machine based on a host-stabilized charge-transfer complex. Angew Chem Int Ed 44:87-91
25. Tan YB, Choi SW, Lee JW, Ko YH, Kim K (2002) Synthesis and characterization of novel side-chain pseudopolyrotaxanes containing cucurbituril. Macromolecules 35:7161-7165
26. Choi S, Park SH, Ziganshina AY, Ko YH, Lee JW, Kim K (2003) A stable cis-stilbene derivative encapsulated in cucurbit[7]uril. Chem Commun 17:2176-2177
27. Tuncel D, Steinke JHG (2004) Catalytic self-threading: a new route for the synthesis of polyrotaxanes. Macromolecules 37:288-302
28. 1-(4-vinylbenzyl)-1, 4-diaminobutane dihydrochloride. Polymer 47:742-750
29. Geng J, Biedermann F, Zayed JM, Tian F, Scherman OA (2011) Supramolecular glycopolymers in water: a reversible route toward multivalent carbohydrate-lectin conjugates using cucurbit[8]uril. Macromolecules 44:4276-4281
30. Yang H, Hao JC, Tan YB (2011) Cucurbit[7]uril moving on side chains of polypseudorotaxanes: synthesis, characterization, and properties. J Polym Sci A Polym Chem 49:2138-2146
31. Wang H, Tan YB, Zhu YJ, Du X, Zhang L (2011) Synthesis and properties of pH-responsive polymers with cadaverine side groups. J Macromol Sci Part A 48:816-822
32. Freeman WA, Mock WL, Shih NY (1981) Cucurbituril. J Am Chem Soc 103:7367-7368
33. Zhu YJ, Tan YB, Du X, Piao JC, Zhou QF (2008) Synthesis and characteristic of double hydrophilic block copolymer with amine pendant chains. Chin Chem Lett 19:355-358
34. Debye P (1947) Molecular-weight determination by light scattering. J Phys Colloid Chem 51:18-32
35. Zimm BH (1948) The scattering of light and the radial distribution function of high polymer solutions. J Chem Phys 16:1093-1099
36. Hou ZS, Tan YB, Zhou QF (2006) Side-chain pseudopolyrotaxanes by threading cucurbituril[6] onto quaternized poly-4-vinylpyridine derivative: synthesis and properties. Polymer 47:5267-5274
37. Zhang HC, Sun LZ, Liu ZN, An W, Hao AY, Xin FF, Shen J (2010) pH-responsive vesicle-like particles based on inclusion complexes between cyclodextrins and methyl orange. Colloid Surface A 358:115-121
38. Zapotoczny S, Rymarczyk-Machal M, Stradomska A, Petelenz P, Nowakowska M (2007) Aggregates of naphthalene chromophores in poly (vinylalcohol)-graft-poly (vinylnaphthalene) pseudomicelles. J Phys Chem B 111:10088-10094
39. Taktak FF, Butun V (2010) Synthesis and physical gels of pHand thermo-responsive tertiary amine methacrylate based ABA triblock copolymers and drug release studies. Polymer 51:3618-3626
40. Torchilin VP (2007) Micellar nanocarriers: pharm perspectives. Pharmaceut Res 24:1-16
41. Gota C, Okabe K, Funatsu T, Harada Y, Uchiyama S (2009) Hydrophilic fluorescent nanogel thermometer for intracellular thermometry. J Am Chem Soc 131:2766-2767
42. de Silva AP, Gunaratne HQN, McCoy CP (1996) Direct visual indication of pH windows: 'off-on-off' fluorescent PET (photoinduced electron transfer) sensors switches. Chem Commun 21:2399-2400
43. Diaz-Fernandez Y, Foti F, Mangano C, Pallavicini P, Patroni S, Perez-Gramatges A, Rodriguez-Calvo S (2006) Micelles for the self-assembly of "off-on-off" fluorescent sensors for pH windows. Chem Eur J 12:921-930