Meta - Para -linked octaaza[18]cyclophanes and their polycationic states

Journal of Organic Chemistry

Volumn 78, Issue 7, 2013, Pages 2947-2956

  Sakamaki, Daisuke ^a   Ito, Akihiro ^a   Furukawa, Ko ^b   Kato, Tatsuhisa ^a   Tanaka, Kazuyoshi ^a  

^a KYOTO UNIVERSITY   (Japan)

^b INSTITUTE FOR MOLECULAR SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CONFORMATIONAL CHANGE; DIFFERENTIAL PULSE VOLTAMMETRY; ELECTROCHEMICAL MEASUREMENTS; MOLECULAR SKELETON; P-PHENYLENE DIAMINES; QUANTUM CHEMICAL CALCULATIONS; SPECTROELECTROCHEMICAL MEASUREMENTS; SPIN-TRIPLET STATE;

CYCLIC VOLTAMMETRY; PARAMAGNETIC RESONANCE; QUANTUM CHEMISTRY; SPECTROELECTROCHEMISTRY; SPIN DYNAMICS;

ELECTRON SPIN RESONANCE SPECTROSCOPY;

CYCLOPHANE DERIVATIVE; METACYCLOPHANE DERIVATIVE; OCTAAZACYCLOPHANE; PARACYCLOPHANE DERIVATIVE; PHENYLENEDIAMINE; UNCLASSIFIED DRUG;

ARTICLE; CYCLIC POTENTIOMETRY; ELECTROCHEMICAL ANALYSIS; ELECTRON SPIN RESONANCE; LOW TEMPERATURE; OXIDATION; QUANTUM MECHANICS;

AZA COMPOUNDS; CATIONS; DIAMINES; ELECTROCHEMICAL TECHNIQUES; MACROCYCLIC COMPOUNDS; MOLECULAR STRUCTURE; POLYMERS; QUANTUM THEORY;

EID: 84875944639     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo3026884     Document Type: Article

References (67)

1. König, B.; Fonseca, M. H. Eur. J. Inorg. Chem. 2000, 2303
2. Wang, M.-X. Chem. Commun. 2008, 4541
3. Maes, W.; Dehaen, W. Chem. Soc. Rev. 2008, 37, 2393
4. Takemura, H. Curr. Org. Chem. 2009, 13, 1633
5. Wang, M.-X. Acc. Chem. Res. 2012, 45, 182
6. Cragg, P. J.; Sharma, K. Chem. Soc. Rev. 2012, 41, 597
7. Chen, P.; Jäkle, F. J. Am. Chem. Soc. 2011, 133, 20142
8. Chen, P.; Lalancette, R. A.; Jäkle, F. Angew. Chem., Int. Ed. 2012, 51, 7994
9. Tsue, H.; Ishibashi, K.; Tamura, R. Top. Heterocycl. Chem. 2008, 17, 73
10. Ito, A.; Tanaka, K. Pure Appl. Chem. 2010, 82, 979
11. Ito, A.; Ono, Y.; Tanaka, K. New J. Chem. 1998, 779
12. Ito, A.; Ono, Y.; Tanaka, K. J. Org. Chem. 1999, 64, 8236
13. Wang, M.-X.; Zhang, X.-H.; Zheng, Q.-Y. Angew. Chem., Int. Ed. 2004, 43, 838
14. Wang, M.-X.; Yang, H.-B. J. Am. Chem. Soc. 2004, 126, 15412
15. Liu, S.-Q.; Wang, D.-X.; Zheng, Q.-Y.; Wang, M.-X. Chem. Commun. 2007, 3856
16. Zhang, E.-X.; Wang, D.-X.; Zheng, Q.-Y.; Wang, M.-X. Org. Lett. 2008, 10, 2565
17. Bushby, R. J.; Kilner, C. A.; Taylor, N.; Vale, M. E. Tetrahedron 2007, 63, 11458
18. Ishibashi, K.; Tsue, H.; Sakai, N.; Tokita, S.; Matsui, K.; Yamauchi, J.; Tamura, R. Chem. Commun. 2008, 2812
19. Vale, M.; Pink, M.; Rajca, S.; Rajca, A. J. Org. Chem. 2008, 73, 27
20. Panagopoulos, A. M.; Zeller, M.; Becker, D. P. J. Org. Chem. 2010, 75, 7887
21. Ito, A.; Yokoyama, Y.; Aihara, R.; Fukui, K.; Eguchi, S.; Shizu, K.; Sato, T.; Tanaka, K. Angew. Chem., Int. Ed. 2010, 49, 8205
22. Tsuchiya, K.; Miyaishi, H.; Ogino, K. Chem. Lett. 2011, 40, 931
23. Wolfe, J. P.; Wagaw, S.; Marcoux, J. F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805
24. Hartwig, J. F. Acc. Chem. Res. 1998, 31, 852
25. Hartwig, J. F. Angew. Chem., Int. Ed. 1998, 37, 2046
26. Muci, A. R.; Buchwald, S. L. Top. Curr. Chem. 2002, 219, 133
27. Bushby, R. J.; McGill, D. R.; Ng, K. M.; Taylor, N. Chem. Commun. 1996, 2641
28. Bushby, R. J.; McGill, D. R.; Ng, K. M.; Taylor, N. J. Chem. Soc., Perkin Trans. 2 1997, 1405
29. Ito, A.; Inoue, S.; Hirao, Y.; Furukawa, K.; Kato, T.; Tanaka, K. Chem. Commun. 2008, 3242
30. Ito, A.; Ono, Y.; Tanaka, K. Angew. Chem., Int. Ed. 2000, 39, 1072
31. Selby, T. D.; Blackstock, S. C. Org. Lett. 1999, 1, 2053
32. Hauck, S. I.; Lakshmi, K. V.; Hartwig, J. F. Org. Lett. 1999, 1, 2057
33. Kulszewicz-Bajer, I.; Maurel, V.; Gambarelli, S.; Wielgus, I.; Djurado, D. Phys. Chem. Chem. Phys. 2009, 11, 1362
34. Sakamaki, D.; Ito, A.; Furukawa, K.; Kato, T.; Tanaka, K. Chem. Commun. 2009, 4524
35. Goodson, F. E.; Hauck, S. I.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 7527
36. To check the influence of optimized macrocyclic structures in 2 and 3 by replacing long n -butoxy groups with short methoxy groups, we carried out semiempirical AM1 (Austin model 1 calculations on both 2, 2′, 3, and 3′. Dewar, M. J. S.; Zoebisch, E. G.; Healy, E. F.; Stewart, J. J. P. J. Am. Chem. Soc. 1985, 107, 3902
37. Tirado-Rives, J.; Jorgensen, W. L. J. Chem. Theory Comput. 2008, 4, 297
38. Zhao, Y.; Truhlar, D. G. J. Chem. Phys. 2006, 125, 194101
39. Zhao, Y.; Truhlar, D. G. Acc. Chem. Res. 2008, 41, 157
40. Zhao, Y.; Truhlar, D. G. Chem. Phys. Lett. 2011, 502, 1
41. Borden, W. T.; Davidson, E. R. J. Am. Chem. Soc. 1977, 99, 4587
42. Dougherty, D. A. Acc. Chem. Res. 1991, 24, 88
43. Huang, W.; Henderson, T. L. E.; Bond, A. M.; Oldham, K. B. Anal. Chim. Acta 1995, 304, 1
44. Ishitani, A.; Nagakura, S. Mol. Phys. 1967, 12, 1
45. Badger, B.; Brocklehurst, B.; Russell, R. D. Chem. Phys. Lett. 1967, 1, 122
46. Szeghalmi, A. V.; Erdmann, M.; Engel, V.; Schmitt, M.; Amthor, S.; Kriegisch, V.; Nöll, G.; Stahl, R.; Lambert, C.; Leusser, D.; Stalke, D.; Zabel, M.; Popp, J. J. Am. Chem. Soc. 2004, 126, 7834
47. Hirao, Y.; Ito, A.; Tanaka, K. J. Phys. Chem. A 2007, 111, 2951
48. Ito, A.; Sakamaki, D.; Ichikawa, Y.; Tanaka, K. Chem. Mater. 2011, 23, 841
49. Ito, A.; Yamagishi, Y.; Fukui, K.; Inoue, S.; Hirao, Y.; Furukawa, K.; Kato, T.; Tanaka, K. Chem. Commun. 2008, 6573
50. Sakamaki, D.; Ito, A.; Furukawa, K.; Kato, T.; Shiro, M.; Tanaka, K. Angew. Chem., Int. Ed. 2012, 51, 12776
51. Bonvoisin, J.; Launay, J.-P.; Van der Auweraer, M.; De Schryver, F. C. J. Phys. Chem. 1994, 98, 5052
52. Bonvoisin, J.; Launay, J.-P.; Van der Auweraer, M.; De Schryver, F. C. J. Phys. Chem. 1996, 100, 18006
53. Bonvoisin, J.; Launay, J.-P.; Verbouwe, W.; Van der Auweraer, M.; De Schryver, F. C. J. Phys. Chem. 1996, 100, 17079
54. Sedó, J.; Ruiz, D.; Vidal-Gancedo, J.; Rovira, C.; Bonvoisin, J.; Launay, J.-P.; Veciana, J. Adv. Mater. 1996, 8, 748
55. Wienk, M. M.; Janssen, R. A. J. J. Am. Chem. Soc. 1997, 119, 4492
56. Rovira, C.; Ruiz-Molina, D.; Elsner, O.; Vidal-Gancedo, J.; Bonvoisin, J.; Launay, J.-P.; Veciana, J. Chem.-Eur. J. 2001, 7, 240
57. The absorption band attributable to the formation of dicationic quinoidal PD structures for N, N, N ′, N ′-tetraanisyl- p -phenlenediamine (TAPD) is observed at 769 nm (1.61 eV): Lambert, C.; Nöll, G. J. Am. Chem. Soc. 1999, 121, 8434
58. Nelsen, S. F.; Konradsson, A. E.; Weaver, M. N.; Telo, J. P. J. Am. Chem. Soc. 2003, 125, 12493
59. Ito, A.; Nakano, Y.; Urabe, M.; Kato, T.; Tanaka, K. J. Am. Chem. Soc. 2006, 128, 2948
60. Bell, F. A.; Ledwith, A.; Sherrington, D. C. J. Chem. Soc. 1969, 2719
61. Connell, N. G.; Geiger, W. E. Chem. Rev. 1996, 96, 877
62. Isoya, J.; Kanda, H.; Norris, J. R.; Tang, J.; Brown, M. K. Phys. Rev. B 1990, 41, 3905
63. Astashkin, A. V.; Schweiger, A. Chem. Phys. Lett. 1990, 174, 595
64. Ito, A.; Sakamaki, D.; Ino, H.; Taniguchi, A.; Hirao, Y.; Tanaka, K.; Kanemoto, K.; Kato, T. Eur. J. Org. Chem. 2009, 4441
65. Mims, W. B. Phys. Rev. B 1972, 5, 2409
66. Shelby, Q.; Kataoka, N.; Mann, G.; Hartwig, J. J. Am. Chem. Soc. 2000, 122, 10718
67. Kataoka, N.; Shelby, Q.; Stambuli, J. P.; Hartwig, J. F. J. Org. Chem. 2002, 67, 5553