Polyrotaxanes and related structures: Synthesis and properties

Current Opinion in Solid State and Materials Science

Volumn 2, Issue 6, 1997, Pages 647-652

  Gong, Caiguo ^a   Gibson, Harry W ^a  

^a VIRGINIA POLYTECHNIC INSTITUTE AND STATE UNIVERSITY   (United States)

Author keywords

BG blocking group; CD cyclodextrin; M n average number of cyclics per repeat unit; PDI polydispersity

Indexed keywords

EID: 0000497907     PISSN: 13590286     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1359-0286(97)80004-6     Document Type: Article

References (37)

1. Gibson HW, Bheda MC, Engen PT. Rotaxanes, catenanes, polyrotaxanes, polycatenanes and related materials. Prog Polym Sci. 19:1994;843-945.
2. Amabalino DB, Stoddart JF. Interlocked and interwined structures and superstructures. Chem Rev. 95:1995;2725-2828.
3. Philp D, Stoddart JF. Self-assembly in natural and unnatural systems. Int Ed Angew Chem. 35:1996;1154-1196.
4. Gibson HW. Rotaxanes. Semlyen JA. Large Ring Molecules. 1995;191-262 J Wiley and Sons, New York.
5. Wenz G, Keller B. Threading cyclodextrin rings on polymer chains. Int Ed Angew Chem. 31:1992;197-199.
6. Wenz G, Wolf F, Wagner M, Kubik S. Topology and molecular chemistry: synthesis, topography and stability of a [2]-rotaxane derived from a lipophilic cyclodextrin derivative. New J Chem. 17:1993;729-738.
7. Wenz G. Speed control for cyclodextrin rings on polymer chains. Macromolecules Symp. 87:1994;11-16.
8. Harada A, Li J, Kamachi M. Synthesis of a tubular polymer from threaded cyclodextrins. Nature. 364:1993;516-518.
9. Harada A, Li J, Kamachi M. Double-stranded inclusion complexes of cyclodextrin threaded on poly(ethylene glycol). Nature. 370:1994;126-129.
10. Harada A, Li J, Kamachi M. Preparation and properties of inclusion complexes of poly(ethylene glycol) with α-cyclodextrin. Macromolecules. 26:1993;5698-5703.
11. Harada A, Li J, Kamachi M. Formation of inclusion complexes of monodisperse oligo(ethylene glycol)s with α-cyclodextrin. Macromolecules. 27:1994;4538-4543.
12. Harada A, Okada M, Li J, Kamachi M. Preparation and characterization of inclusion complexes of poly(propylene glycol) with cyclodextrins. Macromolecules. 28:1995;8406-8411.
13. Gibson HW, Marand H. Polyrotaxanes: molecular composites derived by physical linkage of cyclic and linear species. Adv Mater. 5:1993;11-21.
14. Shen YX, Xie D, Gibson HW. Polyrotaxanes based on polyurethane backbone and crown ether cyclics. 1. Synthesis. J Am Chem Soc. 116:1994;537-548.
15. Gibson HW, Liu S, Lecavalier P, Wu C, Shen YX. Synthesis and preliminary characterization of some polyester rotaxanes. J Am Chem Soc. 117:1995;852-874.
16. Gibson HW, Liu S. Polyrotaxanes: past, present and future. Macromol Symposia. 102:1996;55-59.
17. Delaviz Y, Gibson HW. Macrocyclic polymers, synthesis of poly(amide crown ether)s based on bis(5-carboxy-1,3-phenylene)-32-crown-10. network formation through threading. Macromolecules. 25:1992;4859-4862.
18. Born M, Koch T, Ritter H. Side chain polyrotaxanes: 2. functionalized polysulfone with non-convalently anchored cyclodextrins in the side chains. Acta Polym. 45:1994;68-72.
19. Born M, Ritter H. Side-chain polyrotaxanes with a tandem structure based on cyclodextrins and a polymethacrylate main chain. Int Ed Angew Chem. 34:1995;309-311.
20. Gong C, Gibson HW. Synthesis and characterization of a polyester/crown ether rotaxane derived from a difunctional blocking group. Macromolecules. 29:1996;7029-7033 The difunctional blocking group was used as a diol monomer and thus new evidence for the formation of poly(ester rotaxane)s was introduced. blocking group effectively prevented dethreading and increased m/n. A mechanism for the formation of crown ether-based polyrotaxane was provided. of outstanding interest.
21. Gong C, Gibson HW. Dethreading during the preparation of polyrotaxanes. Macromol Chem Phys. 198:1997;2321-2332 A blocking group was used as a comonomer together with 1,10-decanediol. M/n values of poly(ester rotaxane)s increased with the amount of blocking group among the total diol. The dethreading mechanism was revealed. A range of chemical shifts for threaded 30-crown-10, reflecting polymer sequence structures were observed. of special interest.
22. Gong C, Ji Q, Glass TE, Gibson HW. A strategy to eliminate dethreading during the preparation of poly(ester/crown ether rotaxane)s: use of difunctional blocking groups. Macromolecules. 30:1997;4807-4813 A strategy to eliminate dethreading was provided by using bulky monomers. Thus the polyrotaxane had the highest m/n, and H-bonding between the crown ether and hydroxy group proved to be the driving force for threading. This strategy provided a basis for understanding how other factors affect the threading process. of special interest.
23. Gibson HW, Gong C, Liu S, Nagvekar D. New polymer architectures: recent results with polyrotaxanes. Macromol Symposia. 1997;. in press.
24. Gibson HW, Liu S, Gong C, Ji Q, Joseph E. Studies of the formation of poly(ester rotaxane)s from diacid chlorides, diols and crown ethers & their properties. Macromolecules. 30:1997;3711-3727 The effect of rotaxane formation on polymer properties, that is, intrinsic viscosity and melt viscosity was explored. of outstanding interest.
25. Gong C, Gibson HW. Controlling microstructure in polymeric molecular shuttles: solvent-induced localization of macrocycles in poly(urethane crown ether rotaxane)s. Int Ed Angew Chem. 36:1997;2331-2333 The locus of a threaded crown ether in poly(urethane rotaxane)s was simply controlled by the solvent system, locked at NH sites in chloroform or pushed away from NH sites in dimethylsulfoxide. Thus the reported polyrotaxanes were polymeric molecular shuttles. of outstanding interest.
26. Marand E, Hu Q, Gibson HW, Veytsman B. Spectroscopic characterization of hydrogen bonding in poly(urethane-rotaxane)s. Macromolecules. 29:1996;2555-2562 The H-bonding between the NH group of the polyurethane and the threaded crown ether was identified by infrared spectroscopy of special interest.
27. Gong C, Gibson HW. Self-threading-based approach for branched and/or crosslinked poly(methacrylate rotaxane)s. J Am Chem Soc. 119:1997;5862-5866 A novel strategy for the preparation of mechanically linked branched and crosslinked poly(methacrylate)s was developed by the formation of side chain polyrotaxanes driven by H-bonding of hydroxy groups and the pendant crown ether. of outstanding interest.
28. Gong C, Gibson HW. Controlling polymeric topology by polymerization conditions: mechanically-linked network and branched poly(urethane rotaxane)s with controllable polydispersity. J Am Chem Soc. 119:1997;8585-8591 A novel strategy for the preparation of mechanically linked branched and crosslinked poly(methacrylate)s was developed, driven by H-bonding of hydroxy groups and the crown ether. of outstanding interest.
29. *: poly(ester crown ether)s. Tetrahedron. 58:1997;. in press.
30. Born M, Ritter H. Pseudo-polymer analogous reactions: methylation of alcohol groups of non-covalently anchored 2,6-dimethyl-cyclodextrin components located in branched side chains of a poly(tandem-rotaxane). Adv Mater. 8:1996;149-151 The rigidity of the polymer was increased by threading cyclodextrin and thus the glass transition temperature increased. of outstanding interest.
31. Born M, Ritter H. Topologically unique side-chain polyrotaxanes based on triacetyl-cyclodextrin and a poly(ether sulfone) main chain. Macromol Rapid Commun. 17:1996;197-202 A new topological polyrotaxane was reported; it demonstrated that polymer rigidity can be modified by the formation of the polyrotaxane. of special interest.
32. Weickenmeier M, Wenz G. Cyclodextrin sidechain polyesters-synthesis and inclusion of adamantane derivatives. Macromol Rapid Commun. 17:1996;731-736.
33. Steinbrunn MB, Wenz G. Synthesis of water-soluble inclusion compounds from polyamides and cyclodextrins by solid-state polycondensation. Int Ed Angew Chem. 35:1996;2139-2142 Cyclodextrin was successfully threaded onto polyamides. The resulting polyrotaxanes were soluble in hot water, demonstrating that polymer processibility can be improved by the formation of polyrotaxanes. of outstanding interest.
34. Gong C, Gibson HW. Self assembly of novel polyrotaxanes: Part 1. Main chain polypseudorotaxanes with poly(ester crown ether) backbones. Int Ed Angew Chem. 1998;. in press.
35. Gibson HW, Liu S, Shen YX, Bheda MC, Lee SH, Wang F. The polyrotaxane architecture. A new approach to molecular engineering. 41:1995;58 Kluwer, Dordrecht, The Netherlands. [NATO ASI Series C, vol 456.].
36. Mason PE, Parsons IW, Tolley MS. The first demonstration of molecular queuing in pseudo[n]polyrotaxanes: a novel variant of supramolecular motion. Int Ed Angew fChem. 35:1996;2238-2241 Self-assembly between the hydroquinone repeat units and the bisparaquat cyclophane was applied for the construction of polypseudorotaxanes. The exchange process of the cyclics between bound and free states was studied by NMR. of outstanding interest.
37. Owen J, Hodge P. Synthesis of some new polypseudorotaxanes. J Chem Soc Chem Commun. 1997;11-12 The factors, that is, the properties of host sites, temperature and concentrations, affecting threading of the bisquant cyclophane onto polymers containing electron-rich moeties were studied. of special interest.