Reversibly-Formed Polymeric Capsules

Polymer News

Volumn 25, Issue 2, 2000, Pages 44-52

  Castellano, Ronald K ^a   Nuckolls, Colin ^a   Rebek Jr , Julius ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

Calixarenes; Fibers; Hydrogen bonded polymers; Liquid crystals; Molecular recognition; Self assembly

Indexed keywords

EID: 0007307946     PISSN: 00323918     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (51)

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5. Examples of hydrogen-bonded AA homopolymers include: (a) Hilger, C.; Stadler, R. Makromol. Chem. 1991, 192, 805-817. (b) Sijbesma, R. P.; Beijer, F. H.; Brunsveld, L.; Folmer, B. J. B.; Hirschberg, J. H. K. K.; Lange, R. F. M.; Lowe, J. K. L.; Meijer, E. W. Science 1997, 278, 1601-1604. Folmer, B. J. B.; Cavini, E.; Sijbesma, R. P.; Meijer, E. W. Chem. Commun. 1998, 1847-1848. Folmer, B. J. B.; Sijbesma, R. P.; Meijer, E. W. Polym. Mater. Sci. Eng. 1999, 80, 20-21.
6. Examples of hydrogen-bonded AA homopolymers include: (a) Hilger, C.; Stadler, R. Makromol. Chem. 1991, 192, 805-817. (b) Sijbesma, R. P.; Beijer, F. H.; Brunsveld, L.; Folmer, B. J. B.; Hirschberg, J. H. K. K.; Lange, R. F. M.; Lowe, J. K. L.; Meijer, E. W. Science 1997, 278, 1601-1604. Folmer, B. J. B.; Cavini, E.; Sijbesma, R. P.; Meijer, E. W. Chem. Commun. 1998, 1847-1848. Folmer, B. J. B.; Sijbesma, R. P.; Meijer, E. W. Polym. Mater. Sci. Eng. 1999, 80, 20-21.
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15. Until the discovery of polycaps this connectivity motif had not been explored in the context of hydrogen-bonded polymers.
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33. Freeze-fracture electron microscopy is a common technique for analyzing organic molecules that form gels: (a) Snijder, C. S.; de Jong, J. C.; Meetsma, A.; van Bolhuis, P.; Feringa, B. L. Chem. Eur. J. 1995, 1, 594-597. b) Terech, P.; Weiss, R. G. Chem. Rev. 1997, 97, 3133-3159.
34. Freeze-fracture electron microscopy is a common technique for analyzing organic molecules that form gels: (a) Snijder, C. S.; de Jong, J. C.; Meetsma, A.; van Bolhuis, P.; Feringa, B. L. Chem. Eur. J. 1995, 1, 594-597. b) Terech, P.; Weiss, R. G. Chem. Rev. 1997, 97, 3133-3159.
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37. Spider silk is one example from nature that balances hydrogen bonds in proteins and liquid crystallinity to create a silk fiber with extremely high tensile strength: Simmons, A. H.; Michal, C. A.; Jelinski, L. W. Science 1996, 271, 84-87.
38. For example see: (a) Kato, T.; Fréchet, J. M. J. Macromol. Symp. 1995, 98, 311-326 and references therein. (b) Kato, T. Supramol. Sci. 1996, 3, 53-59. Paleos, C. M.: Tsiourvas, D. Angew. Chem. Int. Ed. Engl. 1995, 34, 1696-1711.
39. For example see: (a) Kato, T.; Fréchet, J. M. J. Macromol. Symp. 1995, 98, 311-326 and references therein. (b) Kato, T. Supramol. Sci. 1996, 3, 53-59. Paleos, C. M.: Tsiourvas, D. Angew. Chem. Int. Ed. Engl. 1995, 34, 1696-1711.
40. For example see: (a) Kato, T.; Fréchet, J. M. J. Macromol. Symp. 1995, 98, 311-326 and references therein. (b) Kato, T. Supramol. Sci. 1996, 3, 53-59. Paleos, C. M.: Tsiourvas, D. Angew. Chem. Int. Ed. Engl. 1995, 34, 1696-1711.
41. Kwolek, S. L.; Morgan, P. W.; Schaefgen, J. R.; Gulrich, L. W. Macromolecules 1977, 10, 1390-1396.
42. For general information on liquid crystals see: (a) Saeva, F. D. Liquid Crystals: The Fourth State of Matter; M. Dekker: New York, 1979. (b) Collings, P. J. Liquid Crystals, Nature's Delicate Phase of Matter; Princeton University Press: Princeton, 1990.
43. For general information on liquid crystals see: (a) Saeva, F. D. Liquid Crystals: The Fourth State of Matter; M. Dekker: New York, 1979. (b) Collings, P. J. Liquid Crystals, Nature's Delicate Phase of Matter; Princeton University Press: Princeton, 1990.
44. Castellano, R. K.; Nuckolls, C.; Eichhorn, S. H.; Wood, M. R.; Lovinger, A. J.; Rebek, J., Jr. Angew. Chem. Int. Ed. 1999, 38, 2603-2606. Host-guest mediated liquid crystallinity has been described for mesogenic calix[4]arenes in the presence of diformamides (B. Xu, T. M. Swager, J. Am. Chem. Soc. 1995, 117, 5011-5012) and for molecular clips (J. L. M. van Nunen, B. F. B. Folmer, R. J. M. Noltle, J. Am. Chem. Soc. 1997, 119, 283-291).
45. Castellano, R. K.; Nuckolls, C.; Eichhorn, S. H.; Wood, M. R.; Lovinger, A. J.; Rebek, J., Jr. Angew. Chem. Int. Ed. 1999, 38, 2603-2606. Host-guest mediated liquid crystallinity has been described for mesogenic calix[4]arenes in the presence of diformamides (B. Xu, T. M. Swager, J. Am. Chem. Soc. 1995, 117, 5011-5012) and for molecular clips (J. L. M. van Nunen, B. F. B. Folmer, R. J. M. Noltle, J. Am. Chem. Soc. 1997, 119, 283-291).
46. Castellano, R. K.; Nuckolls, C.; Eichhorn, S. H.; Wood, M. R.; Lovinger, A. J.; Rebek, J., Jr. Angew. Chem. Int. Ed. 1999, 38, 2603-2606. Host-guest mediated liquid crystallinity has been described for mesogenic calix[4]arenes in the presence of diformamides (B. Xu, T. M. Swager, J. Am. Chem. Soc. 1995, 117, 5011-5012) and for molecular clips (J. L. M. van Nunen, B. F. B. Folmer, R. J. M. Noltle, J. Am. Chem. Soc. 1997, 119, 283-291).
47. Modeling was performed using MacroModel v.5.5 and the MM2* force-field: Mohamadi, F.; Richards, N. G. J.; Guidia, W. C.; Liskamp, R.; Caulfield, R.; Chang, G.; Hendrickson, T.; Still, W. C. J. Comput. Chem. 1990, 11, 440-467.
48. 1H-NMR spectrum of 3a also indicates intramolecular hydrogen bonding. The resonance attributed to the amide proton appears at 8.5-9.0 ppm in all solvents tested and is concentration independent.
49. (a) Simmens, S. C.; Hearle, J. W. S. J. Pohm. Sci. Polym. Phys. Ed. 1980, 18, 871-876.
50. (b) Chawla, K. K. Fibrous Materials: Cambridge University Press: Cambridge, 1998.
51. This graphical depiction is not meant to imply monodispersity