Synthesis and photophysical studies of chiral helical macrocyclic scaffolds via coordination-driven self-assembly of 1,8,9,16-tetraethynyltetraphenylene. Formation of monometallic platinum(II) and dimetallic platinum(II)-ruthenium(II) complexes

Journal of the American Chemical Society

Volumn 132, Issue 46, 2010, Pages 16383-16392

  Lin, Fang ^a   Peng, Hai Yan ^a   Chen, Jing Xing ^a   Chik, David T W ^b   Cai, Zongwei ^b   Wong, Keith M C ^c,d   Yam, Vivian W W ^c,d   Wong, Henry N C ^a,d  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

^b HONG KONG BAPTIST UNIVERSITY   (Hong Kong)

^c UNIVERSITY OF HONG KONG   (Hong Kong)

^d CHINESE UNIVERSITY OF HONG KONG   (Hong Kong)

Author keywords

[No Author keywords available]

Indexed keywords

BUILDING BLOCKES; CHIRAL PROPERTIES; CIRCULAR DICHROISM SPECTRA; COORDINATION-DRIVEN; ELECTROSPRAY MASS SPECTROMETRY; ELEMENTAL ANALYSIS; ENANTIOPURE; INTENSE EMISSION; INTERCONVERSIONS; MACROCYCLES; MACROCYCLICS; NMR SPECTROSCOPY; PHOTOPHYSICAL STUDIES; PLATINUM COMPLEXES; RUTHENIUM COMPLEXES; STRUCTURAL BASIS;

ACETONITRILE; COMPLEXATION; COORDINATION REACTIONS; DICHROISM; FUNCTIONAL GROUPS; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PLATINUM; RUTHENIUM; RUTHENIUM COMPOUNDS; SELF ASSEMBLY;

PLATINUM COMPOUNDS;

1,8,9,16 TETRAETHYNYLTETRAPHENYLENE; 1,8,9,16 TETRAKIS(DIPHENYLPHOSPHINO)TETRAPHENYLENE; ACETONITRILE; COORDINATION COMPOUND; MACROCYCLIC COMPOUND; MOLECULAR SCAFFOLD; NITRILE; PLATINUM COMPLEX; RUTHENIUM COMPLEX; UNCLASSIFIED DRUG;

ARTICLE; BINDING SITE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; CIRCULAR DICHROISM; ELECTROCHEMISTRY; ELECTROSPRAY MASS SPECTROMETRY; ENANTIOSELECTIVITY; INFRARED SPECTROSCOPY; METAL BINDING; MOLECULAR ELECTRONICS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHOTOCHEMISTRY; PROTON NUCLEAR MAGNETIC RESONANCE; SUPRAMOLECULAR CHEMISTRY; SYNTHESIS;

EID: 78649259654     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja106599j     Document Type: Article

References (67)

1. Rapson, W. S., Shuttleworth, R. G., and van Niekerk, J. N. J. Chem. Soc. 1943, 326-327
2. For reviews, see
3. Mak, T. C. W. and Wong, H. N. C. In Comprehensive Supramolecular Chemistry; MacNicol, D. D., Toda, F., and Bishop, R., Eds.; Pergamon Press: Oxford, 1996; Vol. 6, pp 351 - 369.
4. Mak, T. C. W. and Wong, H. N. C. Top. Curr. Chem. 1987, 140, 141-164
5. Huang, N. Z. and Sondheimer, F. Acc. Chem. Res. 1982, 15, 96-102
6. Wong, H. N. C. Acc. Chem. Res. 1989, 22, 145-152
7. Wen, J.-F., Hong, W., Yuan, K., Mak, T. C. W., and Wong, H. N. C. J. Org. Chem. 2003, 68, 8918-8931
8. Lai, C. W., Lam, C. K., Lee, H. K., Mak, T. C. W., and Wong, H. N. C. Org. Lett. 2003, 5, 823-826
9. Hui, C. W., Mak, T. C. W., and Wong, H. N. C. Tetrahedron 2004, 60, 3523-3532
10. Peng, H.-Y., Lam, C.-K., Mak, T. C. W., Cai, Z. W., Ma, W.-T., Li, Y.-X., and Wong, H. N. C. J. Am. Chem. Soc. 2005, 127, 9603-9611
11. Wu, A.-H., Hau, C.-K., and Wong, H. N. C. Adv. Synth. Catal. 2007, 349, 601-608
12. Bachrach, S. M. J. Org. Chem. 2009, 74, 3609-3611
13. Huang, H., Stewart, T., Gutmann, M., Ohhara, T., Niimura, N., Li, Y.-X., Wen, J.-F., Bau, R., and Wong, H. N. C. J. Org. Chem. 2009, 74, 359-369
14. Huang, H., Hau, C.-K., Law, C. C. M., and Wong, H. N. C. Org. Biomol. Chem. 2009, 7, 1249-1257
15. Rajca, A., Safronov, A., Rajca, S., and Shoemaker, R. Angew. Chem., Int. Ed. Engl. 1997, 36, 488-491
16. Marsella, M. J., Kim, I. T., and Tharn, F. J. Am. Chem. Soc. 2000, 122, 974-975
17. Man, Y.-M., Mak, T. C. W., and Wong, H. N. C. J. Org, Chem. 1990, 55, 3214-3221
18. For reviews, see
19. Leininger, S., Olenyuk, B., and Stang, P. J. Chem. Rev. 2000, 100, 853-907
20. Seidel, S. R. and Stang, P. J. Acc. Chem. Res. 2002, 35, 972-983
21. Swiegers, G. F. and Malefetse, T. J. Coord. Chem. Rev. 2002, 225, 91-121
22. Holliday, B. J. and Mirkin, C. A. Angew. Chem., Int. Ed. 2001, 40, 2022-2043
23. Cotton, F. A., Lin, C., and Murillo, C. A. Acc. Chem. Res. 2001, 34, 759-771
24. Fujita, M. Chem. Soc. Rev. 1998, 27, 417-425
25. Lee, S. J. and Lin, W. Acc. Chem. Res. 2008, 41, 521-537
26. Schwab, P. F. H., Levin, M. D., and Michl, J. Chem. Rev. 1999, 99, 1863-1934
27. Fujita, M., Tominaga, M., Hori, A., and Therrien, B. Acc. Chem. Res. 2005, 38, 369-378
28. Ward, M. D. Chem. Commun. 2009, 4487-4499
29. Ziessel, R., Hissler, M., Elghayoury, A., and Harriman, A. Coord. Chem. Rev. 1998, 178-180, 1251-1298
30. Khan, M. S., Kakkar, A. K., Long, N. J., Lewis, J., Raithby, P. R., Marder, T. B., Wittmann, F., and Friend, R. H. J. Mater. Chem. 1994, 4, 1227-1232
31. Yam, V. W.-W., Yu, K.-L., Wong, K. M.-C., and Cheung, K.-K. Organometallics 2001, 20, 721-726
32. Yam, V. W.-W. Acc. Chem. Res. 2002, 35, 555-563
33. Yam, V. W.-W., Wong, K. M.-C., and Zhu, N. Y. J. Am. Chem. Soc. 2002, 124, 6506-6507
34. Yam, V. W.-W., Wong, K. M.-C., and Zhu, N. Y. Angew. Chem., Int. Ed. 2003, 42, 1400-1403
35. Yam, V. W.-W., Chan, K. H.-Y., Wong, K. M.-C., and Chu, B. W.-K. Angew. Chem., Int. Ed. 2006, 45, 6169-6173
36. Katz, T. J. Angew. Chem., Int. Ed. 2000, 39, 1921-1923
37. Graule, S., Rudolph, M., Vanthuyne, N., Autschbach, J., Roussel, C., Crassous, J., and Réau, R. J. Am. Chem. Soc. 2009, 131, 3183-3185
38. Sonogashira, K., Tohda, Y., and Hagihara, N. Tetrahedron Lett. 1975, 16, 4467-4470
39. For review, see
40. Hegedus, L. S. J. Organomet. Chem. 1993, 457, 167-272
41. Alami, M. and Linstrumelle, G. Tetrahedron Lett. 1991, 32, 6109-6112
42. Tamao, K., Sumitani, K., and Kumada, M. J. Am. Chem. Soc. 1972, 94, 4374-4375
43. King, A. O., Okukado, N., and Negishi, E. J. Chem. Soc., Chem. Commun. 1977, 683-684
44. Negishi, E., Okukado, N., and King, A. O. J. Am. Chem. Soc. 1978, 100, 2254-2255
45. Kubota, H. and Rice, K. C. Tetrahedron Lett. 1998, 39, 2907-2910
46. Miller, A. E. G., Biss, J. W., and Schwartzman, L. H. J. Org. Chem. 1959, 24, 627-630
47. Müller, S., Liepold, B., Roth, G. J., and Bestmann, H. J. Synlett 1996, 521-522
48. Roth, G. J., Bernd, L., Müller, S. G., and Bestmann, H. J. Synthesis 2004, 59-62
49. Anderson, S., Neidlein, U., Gramlich, F., and Diederich, F. Angew. Chem., Int. Ed. Engl. 1995, 34, 1596-1600
50. Bähr, A., Droz, A. S., Püntener, M., Neidlein, U., Anderson, S., Seiler, P., and Diederich, F. Helv. Chim. Acta 1998, 81, 1931-1963
51. Droz, A. S. and Diederich, F. J. Chem. Soc., Perkin Trans. 1 2000, 4224-4226
52. Hay, A. S. J. Org. Chem. 1962, 27, 3320-3321
53. Bailey, P. S., Erickson, R. E., Caserio, M. C., and Roberts, J. D. Org. Synth. Coll. Vol. 5 1973, 489-492
54. Ohshiro, N., Takei, F., Onitsuka, K., and Takahashi, S. J. Organomet. Chem. 1998, 569, 195-202
55. Onitsuka, K., Yamamoto, S., and Takahashi, S. Angew. Chem., Int. Ed. 1999, 38, 174-176
56. Lee, S. J., Hu, A., and Lin, W. J. Am. Chem. Soc. 2002, 124, 12948-12949
57. 2NH was stirred for about 48 h in a catalytic amount of CuCl at room temperature, until 3 was completely consumed.
58. -1.
59. Rowan, S. J., Cantrill, S. J., Cousins, G. R. L., Sanders, J. K. M., and Stoddart, J. F. Angew. Chem., Int. Ed. 2002, 41, 898-952
60. Fang, Y.-Q., Polson, M. I. J., and Hanan, G. S. Inorg. Chem. 2003, 42, 5-7
61. 6.
62. Masai, H., Sonogashira, K., and Hagihara, N. Bull. Chem. Soc. Jpn. 1971, 44, 2226-2230
63. Sacksteder, L., Baralt, E., DeGraff, B. A., Lukehart, C. M., and Demas, J. N. Inorg. Chem. 1991, 30, 2468-2476
64. Choi, C. L., Cheng, Y. F., Yip, C., Phillips, D. L., and Yam, V. W. W. Organometallics 2000, 19, 3192-3196
65. Balzani, V. and Scandola, F. Supramolecular Photochemistry; Horwood: Chichester, U.K., 1990.
66. Denti, G., Serroni, S., Campagna, S., Ricevuto, V., and Balzani, V. Coord. Chem. Rev. 1991, 111, 227-236
67. Scandola, F., Indelli, M. T., Chiorboli, C., and Bignozzi, C. A. Top. Curr. Chem. 1990, 158, 73-149