CO2 in supramolecular chemistry: Preparation of switchable supramolecular polymers

Chemistry - A European Journal

Volumn 10, Issue 21, 2004, Pages 5432-5442

  Xu, Heng ^a   Rudkevich, Dmitry M ^a  

^a UNIVERSITY OF TEXAS AT ARLINGTON   (United States)

Author keywords

Calixarenes; Carbon dioxide fixation; Self assembly; Supramolecular chemistry

Indexed keywords

CARBON DIOXIDE; CROSSLINKING; DIMERS; GELS; HYDROGEN BONDS; NANOSTRUCTURED MATERIALS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POLYMERS; SCANNING ELECTRON MICROSCOPY; SELF ASSEMBLY; SOLVENTS;

GUEST MOLECULES; POLYMERIC CHAINS; SUPRAMOLECULAR GEL; SUPRAMOLECULAR POLYMERS;

SUPRAMOLECULAR CHEMISTRY;

AMINE; CALIXARENE; CARBAMIC ACID; CARBON DIOXIDE; INORGANIC SALT; OLIGOMER; POLYMER; SOLVENT; UREA DERIVATIVE;

ARTICLE; CARBON DIOXIDE FIXATION; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; CROSS LINKING; DIMERIZATION; HYDROGEN BOND; MATERIALS; NANOPARTICLE; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; SCANNING ELECTRON MICROSCOPY; STRUCTURE ANALYSIS; SUPRAMOLECULAR CHEMISTRY; SYNTHESIS;

EID: 8344224465     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200306062     Document Type: Article

References (70)

1. a) W. M. Stigliani, T. G. Spiro, Chemistry and the Environment, 2nd ed, Prentice Hall, New Jersey, 2003, pp. 3-178;
2. b) D. S. Schimel, J. I. House, K. A. Hibbard, P. Bousquet, P. Ciais, P. Peylin, B. H. Braswell, M. J. Apps, D. Baker, A. Bondeau, J. Canadell, G. Churkina, W. Cramer, A. S. Denning, C. B. Field, P. Friedlingstein, C. Goodale, M. Heimann, R. A. Houghton, J. M. Melillo, B. Moore, III, D. Murdiyarso, I. Noble, S. W. Pacala, I. C. Prentice, M. R. Raupach, P. J. Rayner, R. J. Scholes, W. L. Steffen, C. Wirth, Nature 2001, 414, 169-172;
3. c) C. V. Cole, J. Duxbury, J. Freney, O. Heinemeyer, K. Minami, A. Mosier, K. Paustian, N. Rosenberg, N. Sampson, D. Sauerbeck, Q. Zhao, Nutr. Cycling Agroecosyst. 1997, 49, 221-228.
4. a) X. Xiaoding, J. A. Moulijn, Energy Fuels 1996, 10, 305-325;
5. b) N. H. Batjes, Biol. Fertil Soils 1998, 27, 230-235.
6. 2 see: c) W. Leitner, Acc. Chem. Res. 2002, 35, 746-756;
7. d) B. Subramanian, C. J. Lyon, V. Arunajatesan, Appl. Catal. B 2002, 37, 279-292.
8. a) D. B. Dell'Amico, F. Calderazzo, L. Labella, F. Marchetti, G. Pampaloni, Chem. Rev. 2003, 103, 3857-3898;
9. b) W. D. McGhee, D. Riley, K. Christ, Y. Pan, B. Parnas, J. Org. Chem. 1995, 60, 2820-2830;
10. c) T. E. Waldman, W. D. McGhee, J. Chem. Soc. Chem. Commun. 1994, 957-958;
11. d) R. N. Salvatore, S. I. Shin, A. S. Nagle, K. W. Jung, J. Org. Chem. 2001, 66, 1035-1037; M. Aresta, E. Quaranta, Tetrahedron 1992, 48, 1515-1530.
12. d) R. N. Salvatore, S. I. Shin, A. S. Nagle, K. W. Jung, J. Org. Chem. 2001, 66, 1035-1037; M. Aresta, E. Quaranta, Tetrahedron 1992, 48, 1515-1530.
13. a) E. M. Hampe, D. M. Rudkevich, Tetrahedron 2003, 59, 9619-9625;
14. b) E. M. Hampe, D. M. Rudkevich, Chem. Commun. 2002, 1450-1451.
15. a) J.-M. Lehn, Polym. Int. 2002, 51, 825-839;
16. b) L. Brunsveld, B. J. B. Folmer, E. W. Meijer, R. P. Sijbesma, Chem. Rev. 2001, 101, 4071-4097;
17. c) C. Schmuck, W. Wienand, Angew. Chem. 2001, 113, 4493-4499; Angew. Chem. Int. Ed. 2001, 40, 4363-4369;
18. c) C. Schmuck, W. Wienand, Angew. Chem. 2001, 113, 4493-4499; Angew. Chem. Int. Ed. 2001, 40, 4363-4369;
19. d) A. T. ten Gate, R. P. Sijbesma, Macromol. Rapid Commun. 2002, 23, 1094-1112;
20. e) U. S. Schubert, C. Eschbaumer, Angew. Chem. 2002, 114, 3016-3050; Angew. Chem. Int. Ed. 2002, 41, 2892-2926.
21. e) U. S. Schubert, C. Eschbaumer, Angew. Chem. 2002, 114, 3016-3050; Angew. Chem. Int. Ed. 2002, 41, 2892-2926.
22. For the preliminary communication of these studies, see: H. Xu, E. M. Hampe, D. M. Rudkevich, Chem, Commun. 2003, 2828-2829.
23. a) T. Yamaguchi, L. M. Boetje, C. A. Koval, R. D. Noble, C. N. Bowman, Ind. Eng. Chem. Res. 1995, 34, 4071-4077;
24. b) T. Yamaguchi, C. A. Koval, R. D. Nobel, C. Bowman, Chem. Eng. Sci. 1996, 51, 4781-4789;
25. c) E. Sada, H. Kumazawa, Z. Han, Chem. Eng. J. 1985, 31, 109-115;
26. d) A. S. Kovvali, K. K. Sirkar, Ind. Eng. Chem. Res. 2001, 40, 2502-2511.
27. E. D. Bates, R. D. Mayton, I. Ntai, J. H. Davis, Jr., J. Am. Chem. Soc. 2002, 124, 926-927.
28. a) M. George, R. G. Weiss, J. Am. Chem. Soc. 2001, 123, 10393-10394;
29. b) M. George, R. G. Weiss, Langmuir 2002, 18, 7124-7135;
30. c) E. Carretti, L. Dei, P. Baglioni, R. G. Weiss, J. Am. Chem. Soc. 2003, 125, 5121-5129;
31. d) M. George, R. G. Weiss, Langmuir 2003, 19, 1017-1025.
32. M. George, R. G. Weiss, Langmuir 2003, 19, 8168-8176, (NMR studies).
33. a) D. M. Rudkevich in Calixarene 2001 (Eds.: Z. Asfari, V. Böhmer, J. Harrowfield, J. Vicens), Kluwer Academic, Dordrecht, 2001, pp. 155-180;
34. b) D. M. Rudkevich, Bull. Chem. Soc. Jpn. 2002, 75, 393-413.
35. a) J. Rebek, Jr., Chem. Commun. 2000, 637-643;
36. b) V. Böhmer, M. O. Vysotsky, Aust. J. Chem. 2001, 54, 671-677;
37. c) F. Hof, S. L. Craig, C. Nuckolls, J. Rebek, Jr., Angew. Chem. 2002, 114, 1556-1578; Angew. Chem. Int. Ed. 2002, 41, 1488-1508.
38. c) F. Hof, S. L. Craig, C. Nuckolls, J. Rebek, Jr., Angew. Chem. 2002, 114, 1556-1578; Angew. Chem. Int. Ed. 2002, 41, 1488-1508.
39. K. D. Shimizu, J. Rebek, Jr., Proc. Natl. Acad. Sci. USA 1995, 92, 12403-12407.
40. a) O. Mogck, V. Böhmer, W. Vogt, Tetrahedron 1996, 52, 8489-8496;
41. b) O. Mogck, E. F. Paulus, V. Böhmer, I. Thondorf, W. Vogt, Chem. Commun. 1996, 52, 2533-2534, (X-ray structure).
42. a) R. K. Castellano, D.M. Rudkevich, J. Rebek, Jr., Proc. Natl. Acad. Sci. USA 1997, 94, 7132-7137;
43. b) R. K. Castellano, J. Rebek, Jr., J. Am. Chem. Soc. 1998, 120, 3657-3663.
44. a) R. K. Castellano, C. Nuckolls, S. H. Eichhorn, M. R. Wood, A. J. Lovinger, J. Rebek, Jr., Angew. Chem. 1999, 111, 2764-2768; Angew. Chem. Int. Ed. 1999, 38, 2603-2606;
45. a) R. K. Castellano, C. Nuckolls, S. H. Eichhorn, M. R. Wood, A. J. Lovinger, J. Rebek, Jr., Angew. Chem. 1999, 111, 2764-2768; Angew. Chem. Int. Ed. 1999, 38, 2603-2606;
46. b) R. K. Castellano, R. Clark, S. L. Craig, C. Nuckolls, J. Rebek, Jr., Proc. Natl. Acad. Sci. USA 2000, 97, 12418-12421.
47. H. Xu, S.P. Stampp, D. M. Rudkevich, Org. Lett. 2003, 5, 4583-4586.
48. H. Xu, G. R. Kinsel, J. Zhang, M. Li, D. M. Rudkevich, Tetrahedron 2003, 59, 5837-5848.
49. R. K. Castellano, S. L. Craig, C. Nuckolls, J. Rebek, Jr., J. Am. Chem. Soc. 2000, 122, 7876-7882.
50. R. B. Martin, Chem. Rev. 1996, 96, 3043-3064.
51. a) R. P. Sijbesma, F. H. Beijer, L. Brunsveld, B. J. B. Folmer, J. H. K. K. Hirschberg, R. F. M. Lange, J. K. L. Lowe, E. W. Meijer, Science 1997, 278, 1601-1604;
52. b) B. J. B. Folmers, R. P. Sijbesma, E. W. Meijer, J. Am. Chem. Soc. 2001, 123, 2093-2094;
53. c) S. H. M. Sontjens, R. P. Sijbesma, M. H. P. van Genderen, E. W. Meijer, Macromolecules 2001, 34, 3815-3818;
54. d) A. T. ten Cate, H. Kooijman, A. L. Spek, R. P. Sijbesma, E. W. Meijer, J. Am. Chem. Soc. 2004, 126, 3801-3808.
55. M. Aresta, D. Ballivet-Tkatchenko, D. B. Dell'Amico, M. C. Bonnet, D. Boschi, F. Calderazzo, R. Faure, L. Labella, F. Marchetti, Chem. Commun. 2000, 1099-1100, and references therein.
56. a) K. Wittmann, W. Wisniewski, R. Mynott, W. Leitner, C. L. Kranemann, T. Rische, P. Eilbracht, S. Kluwer, J. M. Ernsting, C. J. Eisevier, Chem. Eur. J. 2001, 7, 4584-4589;
57. b) A. Fürstner, L. Ackermann, K. Beck, H. Hori, D. Koch, K. Langemann, M. Liebl, C. Six, W. Leitner, J. Am. Chem. Soc. 2001, 123, 9000-9006.
58. Reviews on organogels: a) D. J. Abdallah, R. G. Weiss, Adv. Mater. 2000, 12, 1237-1247;
59. b) J. H. van Esch, B. L. Feringa, Angew. Chem. 2000, 112, 2351-2354; Angew. Chem. Int. Ed. 2000, 39, 2263-2266.
60. b) J. H. van Esch, B. L. Feringa, Angew. Chem. 2000, 112, 2351-2354; Angew. Chem. Int. Ed. 2000, 39, 2263-2266.
61. For pH-switchable supramolecular polymers, see ref. [17]. For tunable cyclic/linear chain in self-assembling polymers: a) M. S. Vollmer, T. D. Clark, C. Steinem, M. R. Ghadiri, Angew. Chem. 1999, 111, 1703-1706; Angew. Chem. Int. Ed. 1999, 38, 1598-1601 (photo switchable); see ref. [21b] (temperature control), see also ref. [5d].
62. For pH-switchable supramolecular polymers, see ref. [17]. For tunable cyclic/linear chain in self-assembling polymers: a) M. S. Vollmer, T. D. Clark, C. Steinem, M. R. Ghadiri, Angew. Chem. 1999, 111, 1703-1706; Angew. Chem. Int. Ed. 1999, 38, 1598-1601 (photo switchable); see ref. [21b] (temperature control), see also ref. [5d].
63. Review on supramolecular chemistry of gases: D. M. Rudkevich, Angew. Chem. 2004, 116, 568-581; Angew. Chem. Int. Ed. 2004, 43, 558-571.
64. Review on supramolecular chemistry of gases: D. M. Rudkevich, Angew. Chem. 2004, 116, 568-581; Angew. Chem. Int. Ed. 2004, 43, 558-571.
65. a) C. D. Gutsche, M. Iqbal, Org. Synth. 1990, 68, 234-237;
66. b) C. D. Gutsche, J. A. Levine, P. K. Sujeeth, J. Org. Chem. 1985, 50, 5802-5806.
67. a) M. Sisido, Y. Imanishi, Macromolecules 1986, 19, 2187-2193;
68. b) A. M. Bray, D. P. Kelly, T. K. Lim, Aust. J. Chem. 1991, 44, 1649-1658.
69. J. H. Jung, Y. Ono, S. Shinkai, Chem. Eur. J. 2000, 6, 4552-4557.
70. R. J. Sime, Physical Chemistry-Methods, Techniques and Experiments, Saunders, Philadelphia, 1990, pp. 522-527.