Self-assembled benzophenone bis-urea macrocycles facilitate selective oxidations by singlet oxygen

Journal of Organic Chemistry

Volumn 78, Issue 11, 2013, Pages 5568-5578

  Geer, Michael F ^a   Walla, Michael D ^a   Solntsev, Kyril M ^b   Strassert, Cristian A ^c   Shimizu, Linda S ^a  

^a UNIVERSITY OF SOUTH CAROLINA   (United States)

^b GEORGIA INSTITUTE OF TECHNOLOGY   (United States)

^c UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

IRRADIATION; METABOLISM; OXYGEN; UREA;

PHOTOPHYSICAL PROPERTIES; PHOTOPRODUCTIONS; RADICAL PATHWAY; SELECTIVE OXIDATION; SELECTIVE OXIDATION PROCESS; SELECTIVE REACTIONS; STABLE ORGANIC RADICALS; TERTIARY ALCOHOLS;

OXIDATION;

BENZOPHENONE; CUMENE; ENDOPEROXIDE; HYDROPEROXIDE; MACROCYCLIC COMPOUND; SINGLET OXYGEN; UREA DERIVATIVE;

ABSORPTION; ARTICLE; CHEMICAL STRUCTURE; COMPLEX FORMATION; MOLECULAR MECHANICS; OXIDATION; OXYGENATION; PHYSICAL CHEMISTRY; SOLID; STEADY STATE; ULTRAVIOLET IRRADIATION;

EID: 84879300501     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo400685u     Document Type: Article

References (72)

1. Hoffmann, N. Chem. Rev. 2008, 108, 1052
2. Kessel, D.; Reiners, J. Isr. J. Chem. 2012, 52, 674
3. Ogilby, P. R. Chem. Soc. Rev. 2010, 39, 3181
4. Ogilby, P. R. Photochem. Photobiol. Sci. 2010, 9, 1543
5. Cuquerella, M. C.; Lhiaubet-Vallet, V.; Cadet, J.; Miranda, M. A. Acc. Chem. Res. 2012, 45, 1558
6. Foote, C. S. Acc. Chem. Res. 1968, 1, 104
7. Clennan, E. L.; Pace, A. Tetrahedron 2005, 61, 6665
8. Lacombe, S.; Pigot, T. Photochemistry 2010, 38, 307
9. Shimizu, L. S.; Smith, M. D.; Hughes, A. D.; Shimizu, K. D. Chem Commun 2001, 1592
10. Shimizu, L. S.; Hughes, A. D.; Smith, M. D.; Davis, M. J.; Zhang, B. P.; zur Loye, H. C.; Shimizu, K. D. J. Am. Chem. Soc. 2003, 125, 14972
11. Dewal, M. B.; Lufaso, M. W.; Hughes, A. D.; Samuel, S. A.; Pellechia, P.; Shimizu, L. S. Chem. Mater. 2006, 18, 4855
12. Dawn, S.; Dewal, M. B.; Sobransingh, D.; Paderes, M. C.; Wibowo, A. C.; Smith, M. D.; Krause, J. A.; Pellechia, P. J.; Shimizu, L. S. J. Am. Chem. Soc. 2011, 133, 7025
13. Yang, J.; Dewal, M. B.; Shimizu, L. S. J. Am. Chem. Soc. 2006, 128, 8122
14. Yang, J.; Dewal, M. B.; Profeta, S.; Smith, M. D.; Li, Y. Y.; Shimizu, L. S. J. Am. Chem. Soc. 2008, 130, 612
15. Dewal, M. B.; Xu, Y. W.; Yang, J.; Mohammed, F.; Smith, M. D.; Shimizu, L. S. Chem Commun 2008, 3909
16. Weiss, R. G.; Ramamurthy, V.; Hammond, G. S. Acc. Chem. Res. 1993, 26, 530
17. Arumugam, S. J. Photochem. Photobiol. A 2008, 199, 242
18. Shailaja, J.; Sivaguru, J.; Robbins, R. J.; Ramamurthy, V.; Sunoj, R. B.; Chandrasekhar, J. Tetrahedron 2000, 56, 6927
19. Pace, A.; Clennan, E. L. J. Am. Chem. Soc. 2002, 124, 11236
20. Chen, Y.-Z.; Wu, L.-Z.; Zhang, L.-P.; Tung, C.-H. J. Org. Chem. 2005, 70, 4676
21. Clennan, E. L. In Advances in Physical Organic Chemistry; Richard, J. P., Ed.; Academic Press: New York, 2008; Vol. 42, p 225.
22. Li, X.; Ramamurthy, V. J. Am. Chem. Soc. 1996, 118, 10666
23. Griesbeck, A. G.; Cho, M. Tetrahedron Lett. 2009, 50, 121
24. Turro, N. J. Modern Molecular Photochemistry, 1 st ed.; University Science Books: Sausalito, 1991.
25. Griesser, M.; Rosspeintner, A.; Dworak, C.; Höfer, M.; Grabner, G.; Liska, R.; Gescheidt, G. Macromolecules 2012, 45, 8648
26. Tehfe, M.-A.; Dumur, F.; Graff, B.; Morlet-Savary, F.; Fouassier, J.-P.; Gigmes, D.; Lalevée, J. Macromolecules 2012, 45, 8639
27. Marin, M. L.; Santos-Juanes, L.; Arques, A.; Amat, A. M.; Miranda, M. A. Chem. Rev. 2011, 112, 1710
28. Lim, K. S.; Oh, K. W.; Kim, S. H. Polym. Int. 2012, 61, 1519
29. Dhende, V. P.; Samanta, S.; Jones, D. M.; Hardin, I. R.; Locklin, J. ACS Appl. Mater. Interfaces 2011, 3, 2830
30. Barash, L.; Wasserman, E.; Yager, W. A. J. Am. Chem. Soc. 1967, 89, 3931
31. Lin, T.-S. J. Chem. Phys. 1972, 57, 2260
32. Murai, H.; Imamura, T.; Obi, K. Chem. Phys. Lett. 1982, 87, 295
33. Qu, B.; Hawthorn, G.; Mau, A. W. H.; Dai, L. J. Phys. Chem. B 2001, 105, 2129
34. Simon, J. D.; Peters, K. S. J. Am. Chem. Soc. 1981, 103, 6403
35. Sakamoto, M.; Cai, X.; Fujitsuka, M.; Majima, T. J. Phys. Chem. A 2006, 110, 11800
36. Hoshino, M.; Shizuka, H. J. Phys. Chem. 1987, 91, 714
37. Lewandowska-Andralojc, A.; Kazmierczak, F.; Hug, G. L.; Horner, G.; Marciniak, B. Photochem. Photobiol. 2013, 89, 14
38. Kuzmanich, G.; Simoncelli, S.; Gard, M. N.; Spanig, F.; Henderson, B. L.; Gudi, D. M.; Garcia-Garibay, M. A. J. Am. Chem. Soc. 2011, 133, 17296
39. Robbins, R. J.; Ramamurthy, V. Chem. Commun. 1997, 1071
40. Adam, W.; Prein, M. Acc. Chem. Res. 1996, 29, 275
41. Ogilby, P. R.; Foote, C. S. J. Am. Chem. Soc. 1982, 104, 2069
42. Sivaguru, J.; Poon, T.; Franz, R.; Jockusch, S.; Adam, W.; Turro, N. J. J. Am. Chem. Soc. 2004, 126, 10816
43. Griesbeck, A. G.; Adam, W.; Bartoschek, A.; El-Idreesy, T. T. Photochem. Photobiol. Sci. 2003, 2, 877
44. Shimizu, L. S.; Hughes, A. D.; Smith, M. D.; Samuel, S. A.; Ciurtin-Smith, D. Supramol. Chem. 2005, 17, 27
45. Sharma, S.; Sinha, S.; Chand, S. Ind. Eng. Chem. Res. 2012, 51, 8806
46. Zhan, W.; Guo, Y.; Wang, Y.; Liu, X.; Guo, Y.; Wang, Y.; Zhang, Z.; Lu, G. J. Phys. Chem. B 2007, 111, 12103
47. Foote, C. S.; Wexler, S.; Ando, W.; Higgins, R. J. Am. Chem. Soc. 1968, 90, 975
48. Trachtenberg, E. N.; Carver, J. R. J. Org. Chem. 1970, 35, 1646
49. Trachtenberg, E. N.; Nelson, C. H.; Carver, J. R. J. Org. Chem. 1970, 35, 1653
50. Stephenson, L. M.; Speth, D. R. J. Org. Chem. 1979, 44, 4683
51. Sharpless, K. B.; Lauer, R. F. J. Am. Chem. Soc. 1972, 94, 7154
52. Shimizu, N.; Bartlett, P. D. J. Am. Chem. Soc. 1976, 98, 4193
53. Lissi, E. A.; Encinas, M. V.; Lemp, E.; Rubio, M. A. Chem. Rev. 1993, 93, 699
54. Long, C. A.; Kearns, D. R. J. Am. Chem. Soc. 1975, 97, 2018
55. Bryant, J. R.; Matsuo, T.; Mayer, J. M. Inorg. Chem. 2004, 43, 1587
56. Zhang, M.; Wang, L.; Ji, H.; Wu, B.; Zeng, X. J. Nat. Gas Chem. 2007, 16, 393
57. Qu, B.; Xu, Y.; Shi, W.; Raanby, B. Macromolecules 1992, 25, 5220
58. Tsierkezos, N. G.; Ritter, U. Phys. Chem. Liq. 2011, 49, 729
59. Lin, A. A.; Sastri, V. R.; Tesoro, G.; Reiser, A.; Eachus, R. Macromolecules 1988, 21, 1165
60. Woodward, J. R.; Lin, T.-S.; Sakaguchi, Y.; Hayashi, H. Mol. Phys. 2002, 100, 1235
61. Kawai, A.; Hirakawa, M.; Abe, T.; Obi, K.; Shibuya, K. J. Phys. Chem. A 2001, 105, 9628
62. Lucarini, M.; Mezzina, E. Electron Paramagn. Reson 2011, 22, 41
63. Nakatsuji, S.; Anzai, H. J. Mater. Chem. 1997, 7, 2161
64. Rawson, J. M.; Alberola, A.; Whalley, A. E. J. Mater. Chem. 2006, 16, 2560
65. Rajca, A. Chem. Rev. 1994, 94, 871
66. Hikcks, R. G. Org. Biomol. Chem. 2007, 5, 1321
67. Polyakov, N. E.; Okazaki, M.; Toriyama, K.; Leshina, T. V.; Fujiwara, Y.; Tanimoto, Y. J. Phys. Chem. 1994, 98, 10563
68. Akiyama, K.; Sekiguchi, S.; Tero-Kubota, S. J. Phys. Chem. 1996, 100, 180
69. Bhosale, S. V.; Jani, C. H.; Langford, S. J. Chem. Soc. Rev. 2008, 37, 331
70. Katz, H. E.; Lovinger, A. J.; Kloc, C.; Siegrist, T.; Li, W.; Lin, Y.-Y.; Dodabalapur, A. Nature 2000, 404
71. Silverman, S. K.; Foote, C. S. J. Am. Chem. Soc. 1991, 113, 7672
72. Foote, C. S. Photochem. Photobiol. 1991, 54, 659