High-spin polyarylmethyl polyradical: Fragment of a macrocyclic 2-strand based upon calix[4]arene rings

Journal of the American Chemical Society

Volumn 119, Issue 43, 1997, Pages 10335-10345

  Rajca, Andrzej ^a   Lu, Kan ^a   Rajca, Suchada ^a  

^a UNIVERSITY OF NEBRASKA LINCOLN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CALIXARENE;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; IN VITRO STUDY; MAGNETIC FIELD; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; TEMPERATURE DEPENDENCE;

EID: 0030668706     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja971493j     Document Type: Article

References (47)

1. Mattis, D. C. The Theory of Magnetism II; Springer-Verlag: Heidelberg, 1985.
2. Mataga, N. Theor. Chim. Acta 1968, 10, 372.
3. For recent reviews on high-spin organic molecules, see: (a) Iwamura, H. Adv. Phys. Org. Chem. 1990, 26, 179.
4. (b) Dougherty, D. A. Acc. Chem. Res. 1991, 24, 88.
5. (c) Iwamura, H.; Koga, N. Acc. Chem. Res. 1993, 26, 346.
6. (d) Rajca, A. Chem. Rev. 1994, 94, 871.
7. (e) Miller, J. S.; Epstein, A. J. Angew. Chem., Int. Ed. Engl. 1994, 33, 385.
8. (f) Yoshizawa, K.; Hoffmann, R. Chem. Eur. J. 1995, 1, 403.
9. Rajca, A. In Molecule-Based Magnetic Materials; Turnbull, M. M., Sugimoto. T., Thompson, L. K., Eds.; ACS Symposium Series 644; American Chemical Society: Washington, DC, 1996; Chapter 17, pp 258-265.
10. For selected attempts to synthesize high-spin organic networks, see: Torrance, J. B.; Oostra, S.; Nazzal, A. Synth. Met. 1987, 19, 709. Bushby, R. J.; Ng, K. M. Chem. Commun. 1996, 659.
11. For selected attempts to synthesize high-spin organic networks, see: Torrance, J. B.; Oostra, S.; Nazzal, A. Synth. Met. 1987, 19, 709. Bushby, R. J.; Ng, K. M. Chem. Commun. 1996, 659.
12. Böhmer, V.; Dörrenbächer, R.; Vogt, W.; Zetta, L. Tetrahedron Lett. 1992, 769. Böhmer, V.; Dörrenbächer, R.; Frings, M.; Heydenreich, M.; de Paoli, D.; Vogt, W.; Ferguson, G.; Thondorf, I. J. Org. Chem. 1996, 61, 549.
13. Böhmer, V.; Dörrenbächer, R.; Vogt, W.; Zetta, L. Tetrahedron Lett. 1992, 769. Böhmer, V.; Dörrenbächer, R.; Frings, M.; Heydenreich, M.; de Paoli, D.; Vogt, W.; Ferguson, G.; Thondorf, I. J. Org. Chem. 1996, 61, 549.
14. For polymacrocyclic DNA fragments, see: Chen, J.; Seeman, N. C. Nature 1991, 350, 631. For a polyphenylene double-helix, see: Rajca, A.; Safronov, A.; Rajca, S.; Schoemaker, R. Angew. Chem., Int. Ed. Engl. 1997, 36, 488.
15. For polymacrocyclic DNA fragments, see: Chen, J.; Seeman, N. C. Nature 1991, 350, 631. For a polyphenylene double-helix, see: Rajca, A.; Safronov, A.; Rajca, S.; Schoemaker, R. Angew. Chem., Int. Ed. Engl. 1997, 36, 488.
16. For macrocyclic polyarylmethyls, see: Rajca, A.; Rajca, S.; Padma-kumar, Angew. Chem., Int. Ed. Engl. 1994, 33, 2091. Rajca, A.; Rajca, S.; Desai, S. R. J. Am. Chem. Soc. 1995, 117, 806.
17. For macrocyclic polyarylmethyls, see: Rajca, A.; Rajca, S.; Padma-kumar, Angew. Chem., Int. Ed. Engl. 1994, 33, 2091. Rajca, A.; Rajca, S.; Desai, S. R. J. Am. Chem. Soc. 1995, 117, 806.
18. For macrocyclic polycarbenes, see: Matsuda, K.; Nakamura, N.; Takahashi, K.; Inoue, K.; Koga, N.; Iwamura, H. J. Am. Chem. Soc. 1995, 117, 5550.
19. Borden, W. T.; Davidson, E. R. J. Am. Chem. Soc. 1977, 99, 4587. Fang, S.; Lee, M.-S.; Hrovat, D. A.; Borden, W. T. J. Am. Chem. Soc. 1995, 117, 6727. Ovchinnikov, A. A. Theor. Chim. Acta 1978, 47, 297. West, A. P., Jr.; Silverman, S. K.; Dougherty, D. A. J. Am. Chem. Soc. 1996, 118, 1452.
20. Borden, W. T.; Davidson, E. R. J. Am. Chem. Soc. 1977, 99, 4587. Fang, S.; Lee, M.-S.; Hrovat, D. A.; Borden, W. T. J. Am. Chem. Soc. 1995, 117, 6727. Ovchinnikov, A. A. Theor. Chim. Acta 1978, 47, 297. West, A. P., Jr.; Silverman, S. K.; Dougherty, D. A. J. Am. Chem. Soc. 1996, 118, 1452.
21. Borden, W. T.; Davidson, E. R. J. Am. Chem. Soc. 1977, 99, 4587. Fang, S.; Lee, M.-S.; Hrovat, D. A.; Borden, W. T. J. Am. Chem. Soc. 1995, 117, 6727. Ovchinnikov, A. A. Theor. Chim. Acta 1978, 47, 297. West, A. P., Jr.; Silverman, S. K.; Dougherty, D. A. J. Am. Chem. Soc. 1996, 118, 1452.
22. Borden, W. T.; Davidson, E. R. J. Am. Chem. Soc. 1977, 99, 4587. Fang, S.; Lee, M.-S.; Hrovat, D. A.; Borden, W. T. J. Am. Chem. Soc. 1995, 117, 6727. Ovchinnikov, A. A. Theor. Chim. Acta 1978, 47, 297. West, A. P., Jr.; Silverman, S. K.; Dougherty, D. A. J. Am. Chem. Soc. 1996, 118, 1452.
23. For selected examples of organic high-spin molecules and polymers, see: Nakamura, K.; Inoue, K.; Iwamura, H. Angew. Chem., Int. Ed. Engl. 1993, 32, 872. Murray, M. A.; Kaszynski, P.; Kaisaki, D. A.; Chang, W.-H.; Dougherty, D. A. J. Am. Chem. Soc. 1994, 116, 8152. Matsuda, K.; Nakamura, N.; Inoue, K.; Koga, N.; Iwamura, H. Bull. Chem. Soc. Jpn. 1996, 69, 1483. Nishide, H.; Kaneko, T.; Nii, T.; Katoh, K.; Tsuschida, E.; Lahti, P. J. Am. Chem. Soc. 1996, 118, 9695.
24. For selected examples of organic high-spin molecules and polymers, see: Nakamura, K.; Inoue, K.; Iwamura, H. Angew. Chem., Int. Ed. Engl. 1993, 32, 872. Murray, M. A.; Kaszynski, P.; Kaisaki, D. A.; Chang, W.-H.; Dougherty, D. A. J. Am. Chem. Soc. 1994, 116, 8152. Matsuda, K.; Nakamura, N.; Inoue, K.; Koga, N.; Iwamura, H. Bull. Chem. Soc. Jpn. 1996, 69, 1483. Nishide, H.; Kaneko, T.; Nii, T.; Katoh, K.; Tsuschida, E.; Lahti, P. J. Am. Chem. Soc. 1996, 118, 9695.
25. For selected examples of organic high-spin molecules and polymers, see: Nakamura, K.; Inoue, K.; Iwamura, H. Angew. Chem., Int. Ed. Engl. 1993, 32, 872. Murray, M. A.; Kaszynski, P.; Kaisaki, D. A.; Chang, W.-H.; Dougherty, D. A. J. Am. Chem. Soc. 1994, 116, 8152. Matsuda, K.; Nakamura, N.; Inoue, K.; Koga, N.; Iwamura, H. Bull. Chem. Soc. Jpn. 1996, 69, 1483. Nishide, H.; Kaneko, T.; Nii, T.; Katoh, K.; Tsuschida, E.; Lahti, P. J. Am. Chem. Soc. 1996, 118, 9695.
26. For selected examples of organic high-spin molecules and polymers, see: Nakamura, K.; Inoue, K.; Iwamura, H. Angew. Chem., Int. Ed. Engl. 1993, 32, 872. Murray, M. A.; Kaszynski, P.; Kaisaki, D. A.; Chang, W.-H.; Dougherty, D. A. J. Am. Chem. Soc. 1994, 116, 8152. Matsuda, K.; Nakamura, N.; Inoue, K.; Koga, N.; Iwamura, H. Bull. Chem. Soc. Jpn. 1996, 69, 1483. Nishide, H.; Kaneko, T.; Nii, T.; Katoh, K.; Tsuschida, E.; Lahti, P. J. Am. Chem. Soc. 1996, 118, 9695.
27. Rajca, S.; Rajca, A. J. Am. Chem. Soc. 1995, 117, 9172.
28. Rajca, A. In Modular Chemistry: Michl, J., Ed.; Kluwer Academic Publications: Dordrecht, The Netherlands; in press.
29. Rajca, A.; Utamapanya, S. J. Am. Chem. Soc. 1993, 115, 10688.
30. Utamapanya, S.; Kakegawa, H.; Bryant, L.; Rajca, A. Chem. Mater. 1993, 5, 1053.
31. For 3,5-dibromophenyllithium, see: Chen, G. J.; Tamborski, C. J. Organomet. Chem. 1983, 251, 149.
32. Rajca, A.; Padmakumar, R.; Smithhisler, D. J.; Desai, R. S.; Ross, C. R.; Stezowski, J. J. J. Org. Chem. 1994, 59, 7701.
33. Detailed analysis of the possible isomers for the annelated triple-calix[4]arenes is complicated because 7B, used in the synthesis, corresponds to one of the two nonsymmetrical isomers of 7. Another problem is the possibility of the noninterconverting (rigid) conformations for the center calix[4]arene ring (ref 6). We thank the reviewer for pointing out rigidity of the center ring in the annelated triple-calix[4]arenes.
34. Rajca, A. J. Am. Chem. Soc. 1990, 112, 5890.
35. Rajca, A.; Rajca, S. J. Am. Chem. Soc. 1996, 118, 8121.
36. + clusters (ref 8).
37. 1 was confirmed by repeating FAB MS analysis for both compounds, using a narrow mass range, high-resolution scan with identical mass calibration.
38. 2H NMR spectrum in a reasonable acquisition time.
39. Carlin, R. L. Magnetochemistry; Springer-Verlag: Berlin, 1986. Also, see: note 28.
40. Heisenberg, W. Z. Phys. 1926, 38, 441. Dirac, P. A. M. Proc. R. Soc. 1926, 112A, 661.
41. Heisenberg, W. Z. Phys. 1926, 38, 441. Dirac, P. A. M. Proc. R. Soc. 1926, 112A, 661.
42. Belorizky, E.; Fries, P. H. J. Chim. Phys. (Paris) 1993, 90, 1077.
43. dia).
44. sat, are obtained; i.e., S = 6.500 in the 1.8-5 K range, as expected for the ground state of the model trimer.
45. Itoh, K. Pure Appl. Chem. 1978, 50, 1251. Jacobs, S. J.; Schultz, D. A.; Jain, R.; Novak, J.; Dougherty, D. A. J. Am. Chem. Soc. 1993, 115, 1744.
46. Itoh, K. Pure Appl. Chem. 1978, 50, 1251. Jacobs, S. J.; Schultz, D. A.; Jain, R.; Novak, J.; Dougherty, D. A. J. Am. Chem. Soc. 1993, 115, 1744.
47. Rajca, A.; Utamapanya, S.; Thayumanavan, S. J. Am. Chem. Soc. 1992, 114, 1884.