C3-symmetrical tribenzotriquinacene derivatives: Optical resolution through cryptophane synthesis and supramolecular self-assembly into nanotubes

Journal of Organic Chemistry

Volumn 78, Issue 3, 2013, Pages 1062-1069

  Wang, Tao ^a   Zhang, Yu Fei ^a   Hou, Qin Qing ^a   Xu, Wen Rong ^b   Cao, Xiao Ping ^a   Chow, Hak Fun ^b   Kuck, Dietmar ^c  

^a LANZHOU UNIVERSITY   (China)

^b CHINESE UNIVERSITY OF HONG KONG   (Hong Kong)

^c BIELEFELD UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ABSOLUTE CONFIGURATION; CRYPTOPHANE; DIASTEREOMERIC; HIGH YIELD; NANOTUBULAR; OPTICAL RESOLUTION; REGIO-SELECTIVE; SUPRAMOLECULAR SELF-ASSEMBLIES;

HYDROCARBONS;

NANOTUBES;

BENZENE DERIVATIVE; NANOTUBE; TRIALDEHYDE; TRIBENZOTRIQUINACENE; TRIMETHANOL; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CHROMATOGRAPHY; COMPLEX FORMATION; OPTICAL RESOLUTION; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SUBSTITUTION REACTION; SYNTHESIS;

EID: 84873379729     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo302470v     Document Type: Article

References (58)

1. Steed, J. W.; Atwood, J. L. Supramolecular Chemistry, 2 nd ed., Wiley: Chichester, 2009.
2. Frömming, K. H. In Comprehensive Supramolecular Chemistry; Atwood, J. L., Lehn, J.-M., Davies, J. E. D., MacNicol, D. D., Vögtle, F., Eds.; Elsevier: Amsterdam, 1996; Vol. 10, p 445.
3. Rudkevitch, D. M.; Leontiev, A. V. Aust. J. Chem. 2004, 57, 713-722
4. Oshovsky, G. V.; Reinhoudt, D. N.; Verboom, W. Angew. Chem., Int. Ed. 2006, 46, 2366-2393
5. Kumar, A.; Sun, S.-S.; Lees, A. J. Coord. Chem. Rev. 2008, 252, 922-939
6. Vriezema, D. M.; Comellas Aragonès, M.; Elemans, J. A. A. W; Cornelissen, J. J. L. M.; Rowan, A. E.; Nolte, R. J. M. Chem. Rev. 2005, 105, 1445-1489
7. Sanders, J. K. M. Chem.-Eur. J. 1998, 4, 1378-1383
8. Hof, F.; Craig, S. L.; Nuckolls, C.; Rebek, J., Jr. Angew. Chem., Int. Ed. 2002, 41, 1488-1508
9. Seidel, S. R.; Stang, P. J. Acc. Chem. Res. 2002, 35, 972-983
10. Dalgarno, S. J.; Power, N. P.; Atwood, J. L. Coord. Chem. Rev. 2008, 252, 825-841
11. Hardie, M. J. Chem. Soc. Rev. 2010, 39, 516-527
12. Hardie, M. J. Israel J. Chem. 2011, 51, 807-816
13. Granzhan, A.; Schouwey, C.; Riis-Johannessen, T.; Scopelliti, R.; Severin, K. J. Am. Chem. Soc. 2011, 133, 7106-7115
14. Garel, L.; Lozach, B.; Dutasta, J. P.; Collet, A. J. Am. Chem. Soc. 1993, 115, 11652-11653
15. Darzac, M.; Brotin, T.; Rousset-Arzel, L.; Bouchu, D.; Dutasta, J.-P. New J. Chem. 2004, 28, 502-512
16. Brotin, T.; Dutasta, J.-P. Chem. Rev. 2009, 109, 88-130
17. Xu, D.; Warmuth, R. J. Am. Chem. Soc. 2008, 130, 7520-7521
18. Percec, V.; Imam, M. R.; Peterca, M.; Wilson, D. A.; Heiney, P. A. J. Am. Chem. Soc. 2009, 131, 1294-1304
19. Kuck, D. Angew. Chem. 1984, 96, 515-516
20. Angew. Chem., Int. Ed. 1984, 23, 508-509.
21. Kuck, D. Top. Curr. Chem. 1998, 196, 167-220
22. Kuck, D. Chem. Rev. 2006, 106, 4885-4925
23. Kuck, D. Pure Appl. Chem. 2006, 78, 749-775
24. Kuck, D.; Schuster, A.; Krause, R. A.; Tellenbröker, J.; Exner, C. P.; Penk, M.; Bögge, H.; Müller, A. Tetrahedron 2001, 57, 3587-3613
25. Kuck, D. In Strained Hydrocarbons. Beyond the Van't Hoff and LeBel Hypothesis; Dodziuk, H., Ed.; Wiley-VCH; Weinheim, 2009; Chapter 9, pp 425-447.
26. Bredenkötter, B.; Henne, S.; Volkmer, D. Chem.-Eur. J. 2007, 13, 9931-9938
27. Georghiou, P. E.; Dawe, L.; Tran, H. A.; Stübe, J.; Neumann, B.; Stammler, H. G.; Kuck, D. J. Org. Chem. 2008, 73, 9040-9047
28. Wang, T.; Li, Z. Y.; Xie, A. L.; Yao, X. J.; Cao, X. P.; Kuck, D. J. Org. Chem. 2011, 76, 3231-3238
29. Langhals, H.; Rauscher, M.; Strübe, J.; Kuck, D. J. Org. Chem. 2008, 73, 1113-1116
30. Vile, J.; Carta, M.; Bezzu, C. G.; McKeown, N. B. Polym. Chem. 2011, 2, 2257-2260
31. Tellenbröker, J.; Kuck, D. Angew. Chem., Int. Ed. 1999, 38, 919-922
32. Kirchwehm, Y.; Damme, A.; Kupfer, T.; Braunschweig, H.; Krüger, A. Chem. Commun. 2012, 48, 1502-1504
33. Mughal, E. U.; Kuck, D. Chem. Commun. 2012, 48, 8880-8882
34. Bong, D. T.; Clark, T. D.; Granja, J. R.; Ghadiri, M. R. Angew. Chem., Int. Ed. 2001, 40, 988-1011
35. Haag, R.; Ohlhorst, B.; Noltemeyer, M.; Fleischer, R.; Stahlke, D.; Schuster, A.; Kuck, D.; de Meijere, A. J. Am. Chem. Soc. 1995, 117, 10474-10485
36. Very recently, a new synthesis of the tribenzotriquinacene framework has been published: Markopoulos, G.; Henneicke, L.; Shen, J.; Okamoto, Y.; Jones, P. G.; Hopf, H. Angew. Chem., Int. Ed. 2012, 51, 12884-12887
37. Poriel, C.; Ferrand, Y.; Maux, P. L.; Rault-Berthelot, J.; Simonneaux, G. Synth. Met. 2008, 158, 796-801
38. Mattiello, L.; Fioravanti, G. Synth. Commun. 2001, 31, 2645-2649
39. Nishida, S.; Morita, Y.; Ueda, A.; Kobayashi, T.; Fukui, K.; Ogasawara, K.; Sato, K.; Takui, T.; Nakasuji, K. J. Am. Chem. Soc. 2008, 130, 14954-14955
40. Wang, T.; Hou, Q. Q.; Teng, Q. F.; Yao, X. J.; Niu, W. X.; Cao, X. P.; Kuck, D. Chem.-Eur. J. 2010, 12, 12412-12424
41. Tellenbröker, J.; Kuck, D. Beilstein J. Org. Chem. 2011, 7, 329-337
42. Strübe, J.; Neumann, B.; Stammler, H. G.; Kuck, D. Chem.-Eur. J. 2009, 15, 2256-2260
43. Borisova, N. E.; Reshetova, M.-D.; Ustynyuk, Y. A. Chem. Rev. 2007, 107, 46-79
44. Jasat, A.; Sherman, J. C. Chem. Rev. 1999, 99, 931-967
45. Chu, Z. L.; Huang, W.; Wang, L.; Gou, S. Polyhedron 2008, 27, 1079-1092
46. Gregoliński, J.; Starynowicz, P.; Hua, K. T.; Lunkley, J. L.; Muller, G.; Lisowski, J. J. Am. Chem. Soc. 2008, 130, 17761-17773
47. Sato, T.; Uno, K. J. Chem. Soc., Perkin Trans. 1 1973, 895-900
48. Yamato, T.; Sakaue, N. J. Chem. Res. (M) 1997, 12, 2615-2646
49. J. Chem. Res. (S) 1997, 12, 440-441.
50. Schmuck, C.; Wienand, W. Synthesis 2002, 655-663
51. Collet, A.; Gottarelli, G. J. Am. Chem. Soc. 1981, 103, 204-205
52. Collet, A.; Gottarelli, G. J. Am. Chem. Soc. 1981, 103, 5912-5913
53. Canceill, J.; Collet, A.; Gabard, J.; Gottarelli, G.; Spada, G. P. J. Am. Chem. Soc. 1985, 107, 1299-1308
54. Collet, A. Tetrahedron 1987, 43, 5725-5759
55. Soler, J. M.; Artacho, E.; Gale, J. D.; García, A.; Junquera, J.; Ordejón, P.; Sánchez-Portal, D. J. Phys.: Condens. Mater 2002, 14, 2745-2779
56. Sánchez-Portal, D.; Ordejón, P.; Artacho, E.; Soler, J. M. Int. J. Quantum Chem. 1997, 65, 453-461
57. Junquera, J.; Paz, O.; Sánchez-Portal, D.; Artacho, E. Phys. Rev. B 2001, 64, 235111-1-9
58. Troullier, N.; Martins, J. L. Phys. Rev. B 1991, 43, 1993-2006