From polynorbornene to the complementary polynorbornene by replication

Angewandte Chemie - International Edition

Volumn 46, Issue 24, 2007, Pages 4481-4485

  Lin, Nai Ti ^a   Lin, Shu Yi ^a   Lee, Shern Long ^a   Chen, Chun Hsien ^a,c   Hsu, Chao Hsiung ^a,b   Hwang, Lian Pin ^a,b   Xie, Zhen Yu ^c   Chen, Chung Hsuan ^a,c   Huang, Shou Ling ^a   Luh, Tien Yau ^a  

^a NATIONAL TAIWAN UNIVERSITY   (Taiwan)

^b ACADEMIA SINICA   (Taiwan)

^c GENOMICS RESEARCH CENTER   (Taiwan)

Author keywords

Ferrocenes; Polynorbornenes; Replication; Ring opening polymerization; Scanning tunneling microscopy

Indexed keywords

FERROCENES; POLYNORBORNENES; REPLICATION PROCESS;

ADHESION; CARBOXYLIC ACIDS; DNA; ESTERS; HYDROLYSIS; MONOMERS; RING OPENING POLYMERIZATION; SCANNING TUNNELING MICROSCOPY;

ELASTOMERS;

BIOMIMETIC MATERIAL; NORBORNANE DERIVATIVE; PLASTIC; POLYMER; POLYNORBORNEN; UNCLASSIFIED DRUG;

ARTICLE; CHEMISTRY;

BIOMIMETIC MATERIALS; NORBORNANES; PLASTICS; POLYMERS;

EID: 34250775929     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200700472     Document Type: Article

References (79)

1. B. Lewin, Gene VII, Oxford University Press, Oxford, 2000, chap. 13.
2. For reviews, see: a) X. Liu, D. R. Liu, Angew. Chem. 2004, 116, 4956-4979;
3. Angew. Chem. Int. Ed. 2004, 43, 4848-4870;
4. b) L. J. Prins, D. N. Reinhoudt, P. Timmerman, Angew. Chem. 2001, 113, 2446-2492;
5. Angew. Chem. Int. Ed. 2001, 40, 2382-2426;
6. c) A. Robertson, A. J. Sinclair, D. Philp, Chem. Soc. Rev. 2000, 29, 141-152;
7. d) L. E. Orgel, Nature 1992, 358, 203-209;
8. e) E. W. Wintner, J. Rebek, Jr., Acta Chem. Scand. 1996, 50, 469-485;
9. f) L. E. Orgel, Acc. Chem. Res. 1995, 28, 109-118.
10. a) L. E. Orgel, R. Lohrmann, Acc. Chem. Res. 1974, 7, 368-377;
11. b) W. S. Zielinski, L. E. Orgel, Nature 1987, 327, 346-347;
12. c) R. Lohrmann, L. E. Orgel, J. Mol. Biol. 1980, 142, 555-567;
13. d) T. Inoue, L. E. Orgel, Science 1983, 219, 859-862;
14. e) C. B. Chen, T. Inoue, L. E. Orgel, J. Mol. Biol. 1985, 181, 271-279;
15. f) T. Inoue, G. F. Joyce, K. Grzeskowiak, L. E. Orgel, J. M. Brown, C. B. Reese, J. Mol. Biol. 1984, 178, 669-676;
16. g) G. von Kiedrowski, Angew. Chem. 1986, 98, 932-934;
17. Angew. Chem. Int. Ed. Engl. 1986, 25, 932-935;
18. h) I. A. Kozlov, B. De Bouvere, A. Van Aerschot, P. Herdewijn, L. E. Orgel, J. Am. Chem. Soc. 1999, 121, 5856-5859;
19. i) I. A. Kozlov, S. Pitsch, L. E. Orgel, Proc. Natl. Acad. Sci. USA 1998, 95, 13 448-13 452;
20. j) I. A. Kozlov, P. K. Politis, A. Van Aerschot, R. Busson, P. Herdewijn, L. E. Orgel, J. Am. Chem. Soc. 1999, 121, 2653-2656;
21. k) I. A. Kozlov, L. E. Orgel, P. E. Nielson, Angew. Chem. 2000, 112, 4462-4465;
22. Angew. Chem. Int. Ed. 2000, 39, 4292-4295;
23. l) J. G. Schmidt, L. Christensen, P. E. Nielsen, L. E. Orgel, Nucleic Acids Res. 1997, 25, 4792-4796;
24. m) I. A. Kozlov, M. Zielinski, B. Allart, L. Kerremans, A. Van Aerschot, R. Busson, P. Herdewijn, L. E. Orgel, Chem. Eur. J. 2000, 6, 151-155;
25. n) A. Luther, R. Brandsch, G. von Kiedrowski, Nature 1998, 396, 245-248;
26. o) T. Li, K. C. Nicolaou, Nature 1994, 369, 218-221.
27. a) Z.-Y. J. Zhan, J. Ye, X. Li, D. G. Lynn, Curr. Org. Chem. 2001, 5, 885-902;
28. b) Z.-Y. J. Zhan, D. G. Lynn, J. Am. Chem. Soc. 1997, 119, 12 420-12 421;
29. c) P. Luo, J. C. Leitzel, Z.-Y. J. Zhan, D. G. Lynn, J. Am. Chem. Soc. 1998, 120, 3019-3031;
30. d) X. Li, Z.-Y. J. Zhan, R. Knipe, D. G. Lynn, J. Am. Chem. Soc. 2002, 124, 746-747;
31. e) X. Li, D. G. Lynn, Angew. Chem. 2002, 114, 4749;
32. Angew. Chem. Int. Ed. 2002, 41, 4567-4569;
33. f) J. T. Goodwin, D. G. Lynn, J. Am. Chem. Soc. 1992, 114, 9197-9198;
34. g) J. C. Leitzel, D. G. Lynn, Chem. Rec. 2001, 1, 53-62;
35. h) K. Fujimoto, S. Matsuda, N. Takahashi, I. Saito, J. Am. Chem. Soc. 2000, 122, 5646-5647.
36. a) D. H. Lee, J. R. Granja, J. A. Martinez, K. Severin, M. R. Ghadiri, Nature 1996, 382, 525-528;
37. b) K. Severin, D. H. Lee, J. A. Martinoz, M. Vieth, M. R. Ghadiri, Angew. Chem. 1998, 110, 133-135;
38. Angew. Chem. Int. Ed. 1998, 37, 126-128;
39. c) D. H. Lee, K. Severin, Y. Yokobayashi, M. R. Ghadiri, Nature 1997, 390, 591-594;
40. d) S. Yao, I. Ghosh, R. Zutshi, J. Chmielewski, Angew. Chem. 1998, 110, 489-492;
41. Angew. Chem. Int. Ed. 1998, 37, 478-481;
42. e) K. S. Severin, D. H. Lee, J. A. Martinoz, M. R. Ghadiri, Chem. Eur. J. 1997, 3, 1017-1024.
43. a) T. Tjivikua, P. Ballester, J. Rebek, Jr., J. Am. Chem. Soc. 1990, 112, 1249-1250;
44. b) Q. Feng, T. K. Park, J. Rebek, Jr., Science 1992, 256, 1179-1180;
45. c) J. I. Hong, Q. Feng, V. Rotello, J. Rebek, Jr., Science 1992, 255, 848-850;
46. d) A. Terfort, G. von Kiedrowski, Angew. Chem. 1992, 104, 626-628;
47. Angew. Chem. Int. Ed. Engl. 1992, 31, 654-656;
48. e) F. Persico, J. D. Wuest, J. Org. Chem. 1993, 58, 95-99;
49. f) B. Wang, I. O. Sutherland, Chem. Commun. 1997, 1495-1496;
50. g) T. R. Kelly, C. Zhao, G. J. Bridger, J. Am. Chem. Soc. 1989, 111, 3744-3745;
51. h) B. G. Bag, G. von Kiedrowski, Angew. Chem. 1999, 111, 3960-3962;
52. Angew. Chem. Int. Ed. 1999, 38, 3713-3714;
53. i) A. Robertson, D. Philp, N. Spencer, Tetrahedron 1999, 55, 11 365-11 384;
54. j) M. Kindermann, I. Stahl, M. Reimild, W. M. Pankau, G. von Kiedrowski, Angew. Chem. 2005, 117, 6908-6913;
55. Angew. Chem. Int. Ed. 2005, 44, 6750-6755;
56. k) E. Kassianidis, R.J. Pearson, D. Philp, Org. Lett. 2005, 7, 3833-3836;
57. l) G. von Kiedrowski, L.-H. Eckardt, K. Naumann, W. M. Pankau, M. Reimold, M. Rein, Pure Appl. Chem. 2003, 75, 609-619;
58. m) V. Zykov, E. Mytilinaios, B. Adams, H. Lipson, Nature 2005, 435, 163-164.
59. a) P. Schwab, R. H. Grubbs, J. W. Ziller, J. Am. Chem. Soc. 1996, 118, 100-110;
60. b) J. G. Hamilton in Handbook of Metathesis, Vol. 3 (Ed.: R.H. Grubbs), Wiley-VCH, Weinheim, 2003, pp. 143-179;
61. c) C. Slugovc, Macromol. Rapid Commun. 2004, 25, 1283.
62. H.-C. Yang, S.-Y. Lin, H.-c. Yang, C.-L. Lin, L. Tsai, S.-L. Huang, I.-W. P. Chen, C.-h. Chen, B.-Y. Jin, T.-Y. Luh, Angew. Chem. 2006, 118, 740-744;
63. Angew. Chem. Int. Ed. 2006, 45, 726-730.
64. a) J. R. L. Smith, J. M. Linford, L. C. Mckeer, P. M. Morris, J. Chem. Soc. Perkin Trans. 2 1984, 1099-1105;
65. b) L. Bernard, M. Joseph, G. Philippe, Tetrahedron Lett. 1989, 30, 1939-1942;
66. c) A. S. Martin, Z. Michael, V. Baburao, M. Ismail, J. Org. Chem. 1976, 41, 2502-2503;
67. d) A. J. Poss, R. K. Belter, J. Org. Chem. 1988, 53, 891-893;
68. e) F. Z. Dörwald, Side Reactions in Organic Synthesis: A Guide to Successful Synthesis Design, Wiley-VCH, Weinheim, 2005.
69. a) W.-Y. Lin, M. G. Murugesh, S. Sudhakar, H.-C. Yang, H.-C. Tai, C.-S. Chang, Y.-H. Liu, Y. Wang, I-W. P. Chen, C.-h. Chen, T.-Y. Luh, Chem. Eur. J. 2006, 12, 324-330;
70. b) W.-Y. Lin, H.-W. Wang, Z.-C. Liu, J. Xu, C.-W. Chen, Y.-C. Yang, S.-L. Huang, H.-C. Yang, T.-Y. Luh, Chem. Asian J. 2007, DOI: 10.1002/ asia.200700011.
71. a) The details are described in the Supporting Information; b) Abbreviations: TBDMS = tert-butyldimethylsilyl, DIAD = diisopropylazodicarboxylate, TBAF = tetrabutylammonium fluoride, DMAP = 4-dimethylaminopyridine.
72. a) P. G. Gassman, P. K. G. Hodgson, R. J. Balchunis, J. Am. Chem. Soc. 1976, 98, 1275-1276;
73. b) P. G. Gassman,, W. N. Schenk, J. Org. Chem. 1977, 42, 918-920.
74. a) R. Dembinski, Eur. J. Org. Chem. 2004, 2763-2773;
75. b) D. L. Hughes, Org. React. 1992, 42, 335-656.
76. n = 3673, PDI = 1.1). Presumably, the reaction may take place from both ends of 12, resulting in a decrease in the number of repeat units in 18.
77. C. R. Clemmer, T. P. Beebe, Jr., Science 1991, 251, 640-642.
78. It is known that 4-aminobenzyl esters may yield an iminiumquinone methide intermediate (reference [9]), which may undergo various kinds of reactions with nucleophiles, leading to a mixture of products and/or polymers (reference [9d]).
79. T. Sato, J. Otera, H. Nozaki, J. Org. Chem. 1992, 57, 2166-2169.