2-Aminopyrimidine directed self-assembly of zinc porphyrins containing bulky 3,5-di-tert-butylphenyl groups

Journal of the American Chemical Society

Volumn 125, Issue 14, 2003, Pages 4233-4239

  Balaban, Teodor Silviu ^a   Goddard, Richard ^b   Linke Schaetzel, Myriam ^a   Lehn, Jean Marie ^a,c  

^a KARLSRUHE INSTITUTE OF TECHNOLOGY   (Germany)

^b MAX PLANCK INSTITUT FÜR KOHLENFORSCHUNG   (Germany)

^c UNIVERSITÉ LOUIS PASTEUR   (France)

Author keywords

[No Author keywords available]

Indexed keywords

SELF ASSEMBLY; SUPRAMOLECULAR CHEMISTRY; THERMAL EFFECTS; TOLUENE; ZINC COMPOUNDS;

ZINC PORPHYRINS;

PORPHYRINS;

BACTERIOCHLOROPHYLL; HYDROGEN; PHENYL GROUP; PORPHYRIN DERIVATIVE; PYRIMIDINE DERIVATIVE; TOLUENE; ZINC;

ARTICLE; CALCULATION; CARBON NUCLEAR MAGNETIC RESONANCE; HYDROGEN BOND; MASS SPECTROMETRY; MOLECULAR MODEL; NUCLEAR MAGNETIC RESONANCE; PROTON NUCLEAR MAGNETIC RESONANCE; TEMPERATURE DEPENDENCE; ULTRAVIOLET SPECTROSCOPY; X RAY ANALYSIS;

BACTERIAL PROTEINS; BACTERIOCHLOROPHYLLS; BIOMIMETIC MATERIALS; HYDROGEN BONDING; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; METALLOPORPHYRINS; MODELS, MOLECULAR; PYRIMIDINES; ZINC;

EID: 0242669329     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja029548r     Document Type: Article

References (78)

1. Balaban, T. S.; Eichhöfer, A.; Lehn, J.-M. Eur. J. Org. Chem. 2000, 4047-4057.
2. (a) Balaban, T. S.; Holzwarth, A. R.; Schaffner, K.; Boender, G.-J.; de Groot, H. J. M. Biochemistry 1995, 34, 15259-15266.
3. (b) Jesorka, A.; Balaban, T. S.; Holzwarth, A. R.; Schaffner, K. Angew. Chem., Int. Ed. Engl. 1996, 35, 2861-2863.
4. (c) Balaban, T. S.; Tamiaki, H.; Holzwarth, A. R.; Schaffner, K. J. Phys. Chem. 1997, 101, 3424-3431.
5. (d) Balaban, T. S.; Leitich, J.; Holzwarth, A. R.; Schaffner, K. J. Phys. Chem. B 2000, 104, 1362-1372.
6. For recent reviews on solar energy conversion, see: (a) Grätzel, M. Nature 2001, 414, 338-344. (b) Grätzel, M.; Moser, J.-E. In Electron Transfer in Chemistry, Vol. 5; Balzani, V., Ed.; Wiley-VCH: Weinheim, Germany, 2001; pp 589-644.
7. For recent reviews on solar energy conversion, see: (a) Grätzel, M. Nature 2001, 414, 338-344. (b) Grätzel, M.; Moser, J.-E. In Electron Transfer in Chemistry, Vol. 5; Balzani, V., Ed.; Wiley-VCH: Weinheim, Germany, 2001; pp 589-644.
8. (a) Bach, U.; Lupo, D.; Comte, P.; Moser, J. E.; Weissörtel, F.; Salbeck, J.; Spreitzer, H.; Grätzel, M. Nature 1998, 395, 583-585.
9. (b) Brabec, C. J.; Shaheen, S. E.; Fromherz, T.; Padinger, F.; Hummelen, J. C.; Dhanabalan, A.; Janssen, R. A. J.; Sariciftci, N. S. Synth. Met. 2001, 121, 1517-1520.
10. (a) Barkigia, K. M.; Fajer, J.; Smith, K. M.; Williams, G. J. B. J. Am. Chem. Soc. 1981, 103, 5890-5893.
11. (b) Smith, K. M.; Goff, D. A.; Fajer, J.; Barkigia, K. M. J. Am. Chem. Soc. 1982, 104, 3747-3749.
12. (a) Stibrany, R. T.; Vasudevan, J.; Knapp, S.; Potenza, J. A.; Emge, T. J.; Schugar, H. J. J. Am. Chem. Soc. 1996, 118, 3980-3981.
13. (b) Vasudevan, J.; Stibrany, R. T.; Bumby, J.; Knapp, S.; Potenza, J. A.; Emge, T. J.; Schugar, H. J. J. Am. Chem. Soc. 1996, 118, 11676-11677.
14. (c) Barkigia, K. M.; Melamed, D.; Sweet, R. M.; Smith, K. M.; Fajer, J. Spectrochim. Acta Part A 1997, 53A, 463-469.
15. (a) Kumar, R. K.; Balasubramanian, S.; Goldberg, I. Chem. Commun. 1998, 1435-1436.
16. (b) Sharma, C. V. K.; Broker, G. A.; Huddleston, J. G.; Baldwin, J. W.; Metzger, R. M.; Rogers, R. D. J. Am. Chem. Soc. 1999, 121, 1137-1144.
17. (c) Fan, J.; Whiteford, J. A.; Olenyuk, B.; Levin, M. D.; Stang, P. J.; Fleischer, E. B. J. Am. Chem. Soc. 1999, 121, 2741-2752.
18. (d) Burrell, A. K.; Jones, B. M.; Hall, S. B.; Officer, D. L.; Reid, D. C. W.; Wild, K. Y.; J. Inclusion Phenom. Macrocycl. Chem. 1999, 35, 185-190.
19. (e) Iengo, E.; Milani, B.; Zangrando, E.; Geremia, S.; Alessio, E. Angew. Chem., Int. Ed. 2000, 39, 1096-1099.
20. (f) Kondo, M.; Kimura, Y.; Wada, K.; Mizutani, T.; Ito, Y.; Kitagawa, S. Chem. Lett. 2000, 818-819.
21. (g) Fujita, N.; Biradha, K.; Fujita, M.; Sakamoto, S.; Yamaguchi, K. Angew. Chem., Int. Ed. 2001, 40, 1718-1721.
22. (h) Shi, X.; Barkigia, K. M.; Fajer, J.; Drain, C. M. J. Org. Chem. 2001, 66, 6513-6522.
23. (i) Redman, J. E.; Feeder, N.; Teat, S. J.; Sanders, J. K. M. Inorg. Chem. 2001, 40, 2486-2499.
24. (j) Bond, A. D.; Feeder, N.; Teat, S. J.; Clyde-Watson, Z.; Bampos, N.; Sanders, J. K. M. Acta Crystallogr. 2001, E57, m454-m456.
25. (a) Drain, C. M.; Fischer, R.; Nolen, E. G.; Lehn, J.-M. J. Chem. Soc., Chem. Commun. 1993, 243-245.
26. (b) Drain, C. M.; Lehn, J.-M. J. Chem. Soc., Chem. Commun. 1994, 2313-2315.
27. (c) Drain, C. M.; Russel, K. C.; Lehn, J.-M. Chem. Commun. 1996, 337-338.
28. (a) Sessler, J. L.; Capuano, V. L.; Burrell, A. K. Inorg. Chim. Acta. 1993, 204, 93-101.
29. (b) Drain, C. M.; Nifiatis, F.; Vasenko, A.; Batteas, J. D. Angew. Chem., Int. Ed. 1998, 2344, 4-2347.
30. (c) Haycock, R. A.; Yartsev, A.; Michelsen, U.; Sundstöm, V.; Hunter, C. A. Angew. Chem., Int. Ed. 2000, 39, 3616-3619.
31. (d) Haycock, R. A.; Hunter, C. A.; James, D. A.; Michelsen, U.; Sutton, L. R. Org. Lett. 2000, 2, 2435-2438.
32. (a) Chernook, A. V.; Rempel, U.; von Borczyskowski, C.; Shulga, A. M.; Zenkevich, E. I. Chem. Phys. Lett. 1996, 254, 229-241.
33. (b) Kobayashi, K.; Koyanagi, M.; Endo, K.; Masuda, H.; Aoyama, Y. Chem. Eur. J. 1998, 4, 417-424.
34. (c) Willert, A.; Bachilo, S.; Rempel, U.; Shulga, A.; Zenkevich, E.; von Borczyskowski, C. J. Photochem. Photobiol. A Chem. 1999, 126, 99-109.
35. (d) Ruhlmann, L.; Schulz, A.; Giraudeau, A.; Messerschmidt, C.; Fuhrhop, J.-H. J. Am. Chem. Soc. 1999, 121, 6664-6667.
36. (e) Ogawa, K.; Kobuke, Y. Angew. Chem., Int. Ed. 2000, 39, 4070-4073.
37. (f) Nagata, N.; Kugimiya, N. S.; Kobuke, Y. Chem. Commun. 2001, 689-690.
38. (g) Ogawa, K.; Zhang, T.; Yosihara, K.; Kobuke, Y. J. Am. Chem. Soc. 2002, 124, 22-23.
39. (a) Vicente, M. G. H.; Jaquinod, L.; Smith, K. M. Chem. Commun. 1999, 1771-1782.
40. (b) Burrell, A. K.; Officer, D. L.; Plieger, P. G.; Reid, D. C. W. Chem. Rev. 2001, 101, 2751-2796.
41. (a) Reimers, J. R.; Lü, T. X.; Crossley, M. J.; Hush, N. S. Nanotechnology 1996, 7, 424-429.
42. (b) Taylor, P. N.; Huuskonen, J.; Rumbles, G.; Aplin, R. T.; Williams, E.; Anderson, H. L. Chem. Commun. 1998, 909-910.
43. (c) Wilson, G. S.; Anderson, H. L. Chem. Commun. 1999, 1539-1540.
44. (d) Mongin, O.; Schuwey, A.; Vallot, M.-A.; Gossauer, A. Tetrahedron Lett. 1999, 40, 8347-8350.
45. (e) Mongin, O.; Hoyler, N.; Gossauer, A. Chem. Eur. J. 2000, 1193-1197.
46. (f) Rucareanu, S.; Mongin, O.; Schuwey, A.; Hoyler, N.; Gossauer, A.; Amrein, W.; Hediger, H.-U. J. Org. Chem. 2001, 66, 4973-4988.
47. (g) Sugiura, K.; Tanaka, H.; Matsumoto, T.; Kawai, T.; Sakata, Y. Chem. Lett. 1999, 1193-1194.
48. (h) Sugiura, K.; Fujimoto, Y.; Sakata, Y. Chem. Commun. 2000, 1105-1106.
49. (a) Holten, D.; Bocian, D. F.; Lindsey, J. S. Acc. Chem. Res. 2002, 35, 57-69.
50. (b) Gust, D.; Moore, T. A.; Moore, A. L. Pure Appl. Chem. 1998, 70, 2189-2200.
51. Lehn, J.-M. Supramolecular Chemistry. Concepts and Perspectives, VCH: Weinheim, 1995.
52. (a) Krische, M. J.; Lehn, J.-M.; Kyritsakas, N.; Fischer, J. Helv. Chim. Acta 1998, 81, 1909-1920.
53. (b) Krische, M. J.; Lehn, J.-M.; Kyritsakas, N.; Fischer, J.; Wegelius, E. K.; Nissinen, M. J.; Rissanen, K. Helv. Chim. Acta 1998, 87, 1921-1930.
54. (c) Krische, M. J.; Lehn, J.-M.; Kyritsakas, N.; Fischer, J.; Wegelius, E. K.; Rissanen, K. Tetrahedron 2000, 56, 6701-6706.
55. (d) Balaban, T. S.; Krische, M. J.; Lehn, J.-M., unpublished results.
56. (a) Susumu, K.; Shimidzu, T.; Tanaka, K.; Segawa, H. Tetrahedron Lett. 1996, 37, 8399-8402.
57. (b) Bhuiyan, A. A.; Seth, J.; Yoshida, N.; Osuka, A.; Bocian, D. F. J. Phys. Chem. B 2000, 104, 10757-10764.
58. (c) Tamiaki, H.; Nagata, Y.; Tsuduki, S. Eur. J. Org. Chem. 1999, 2471-2473.
59. (d) Tsuda, A.; Nakano, A.; Furuta, H.; Yamochi, H.; Osuka, A. Angew. Chem., Int. Ed. 2000, 39, 558-560.
60. (e) Yoshida, N.; Aratani, N.; Osuka, A. Chem. Commun. 2000, 197-198.
61. (f) Screen, T. E. O.; Blake, I. M.; Ress, L. H.; Clegg, W.; Borwich, S. J.; Anderson, H. L. J. Chem. Soc., Perkin Trans., 2002, 320-329.
62. -3.
63. The four Zn atoms are coplanar and describe an approximate rhombus. Distances (Å): Zn1-Zn2 8.330(1), Zn1-Zn2* 8.558(1), Zn1-Zn1* 9.073(1). The mean planes of the two independent porphyrin macrocycles make angles of 65 and 85° to the rhombus plane, and the two central porphyrin rings (blue/green) are 8.77 Å apart.
64. (a) Schachter, A. M. J. Chem. Soc., Chem. Commun. 1988, 960-961.
65. (b) Fleischer, E. B.; Schachter, A. M. Inorg. Chem. 1991, 30, 3763-3769.
66. (c) Krupitsky, H.; Stein, Z.; Goldberg, I.; Strouse, C. E. J. Inclusion Phenom. Macrocycl. Chem. 1994, 18, 177-192.
67. Program SYBYL 6.2 (Tripos Associates, Inc., St. Louis, MO); force field Tripos version 5.2, nonbonded cutoff 8 Å.
68. 4.
69. Although coordination of the amine function to the metal is also conceivable, there is no evidence that this ever occurs in the case of 2-aminopyrimidine.
70. Furberg, S.; Grogaard, G.; Smedsnid, B. Acta Chem. Scand. Ser. B 1979, 33, 715-724.
71. Aakeroy, C. B.; Nieuwenhuyzen, M.; Price, S. L. J. Am. Chem. Soc. 1998, 120, 8986-8993.
72. While the noncoordinating pyrimidinic nitrogens have negative partial charges (-0.17), ligation of a porphyrinic zinc atom leads to a partial positive charge (+0.11) which enhances the polarization of the neighbouring N-H bonds leading to tighter inter-tetrameric hydrogen bonding.
73. Six of the sites are only half occupied in the crystal, resulting in a molecular formula containing 23 cyclohexane molecules.
74. Dunitz, J. D.; Gavezzotti, A. Acc. Chem. Res. 1999, 32, 677-684.
75. (a) Bym, M. P.; Curtis, C. J.; Khan, S. I.; Sawin, P. A.; Tsurumi, R.; Strouse, C. E. J. Am. Chem. Soc. 1990, 112, 1865-1874.
76. (b) Kumar, K. R.; Goldberg, I. Chem. Commun. 1998, 1435-1436.
77. (c) Diskin-Posner, Y.; Goldberg, I. Chem. Commun. 1999, 1961-1962.
78. (d) Diskin-Posner, Y.; Dahal, S.; Goldberg, S. I. Angew. Chem., Int. Ed. 2000, 39, 1288-1292.