Photoresponsive receptors for binding and releasing anions

Journal of Physical Organic Chemistry

Volumn 26, Issue 2, 2013, Pages 79-86

  Lee, Semin ^a   Flood, Amar H ^a  

^a INDIANA UNIVERSITY   (United States)

Author keywords

anion recognition; azobenzene; foldamers; host guest chemistry; molecular switches; noncovalent interactions; photocaged compounds; photoisomerization; pre organization

Indexed keywords

ANION RECOGNITION; FOLDAMERS; HOSTGUEST CHEMISTRY; MOLECULAR SWITCHES; NON-COVALENT INTERACTION; PHOTOCAGED COMPOUNDS; PRE-ORGANIZATION;

AZOBENZENE; BINDING ENERGY; PHOTOISOMERIZATION; STOICHIOMETRY;

NEGATIVE IONS;

EID: 84872899130     PISSN: 08943230     EISSN: 10991395     Source Type: Journal    
DOI: 10.1002/poc.2973     Document Type: Conference Paper

References (66)

1. B. L. Feringa, Molecular switches, Wiley-VCH: Weinheim, 2001.
2. E. R. Kay, D. A. Leigh, F. Zerbetto, Angew. Chem. Int. Ed. 2007, 46, 72-191.
3. The specific requirements to designate a molecule as a machine is still under consideration. See:, A. Coskun, M. Banaszak, R. D. Astumian, J. F. Stoddart, B. A. Grybowski, Chem. Soc. Rev. 2012, 41, 19-30.
4. D. S. Goodsell, The machinery of life, Springer, Telos, 1992.
5. J. Wang, B. L. Feringa, Science 2011, 331, 1429-1432.
6. H. Meng, M. Xue, T. Xia, Y.-L. Zhao, F. Tamanoi, J. F. Stoddart, J. I. Zink, A. E. Nel, J. Am. Chem. Soc. 2010, 132, 12690-12697.
7. T. Muraoka, K. Kinbara, Y. Kobayashi, T. Aida, J. Am. Chem. Soc. 2003, 125, 5612-5613.
8. B. A. Moyer, P. V. Bonnsesen, R. Custelcean, L. H. Delmau, B. P. Hay, Kem. Ind. 2005, 54, 65-87.
9. C. H. Park, H. E. Simmons, J. Am. Chem. Soc. 1968, 90, 2431-2432.
10. P. D. Beer, Chem. Soc. Rev. 1989, 18, 409-450.
11. Q.-Y. Cao, T. Pradhan, S. Kim, J. S. Kim, Org. Lett. 2011, 13, 4386-4389.
12. H. Juwarker, J.-m. Suk, K.-S. Jeong, Chem. Soc. Rev. 2009, 38, 3316-3325.
13. S. Shinkai, in Molecular switches, (Eds:, B. L. Feringa,) Wiley-VCH: Weinheim, 2001.
14. L. O. Essen, Curr. Opin. Struct. Biol. 2002, 12, 516-522.
15. B. Schobert, J. K. Lanyi, J. Biol. Chem. 1982, 257, 10306-10313.
16. D. Oesterhelt, M. Kolbe, H. Besir, L. O. Essen, Science 2000, 288, 1390-1396.
17. H. Kaufmann, S. M. Vratsanos, B. F. Erlanger, Science 1968, 162, 1487-1489.
18. J. Bieth, N. Wassermann, S. M. Vratsanos, B. F. Erlanger, Proc. Nat. Acad. Sci. U.S.A. 1969, 66, 850-854.
19. I. V. Berezin, S. D. Varfolomeyez, A. M. Klibanov, K. Martinek, FEBS Lett. 1974, 39, 329-331.
20. I. Karube, Y. Nakamoto, S. Suzuki, Biochim. Biophys. Acta 1976, 445, 774-779.
21. A. A. Beharry, G. A. Woolley, Chem. Soc. Rev. 2011, 40, 4422-4437.
22. K. L. Haas, K. J. Franz, Chem. Rev. 2009, 109, 4921-4960.
23. S. Shinkai, T. Ogawa, T. Nakaji, Y. Kusano, O. Nanabe, Tetrahedron Lett. 1979, 20, 4569-4572.
24. F. Cramer, W. Dietsche, Chem. Ber. 1959, 92, 378-384.
25. N. Hennrich, F. Cramer, J. Am. Chem. Soc. 1965, 87, 1121-1126.
26. See review, W. D. Griffiths, M. L. Bender, Adv. Catal. 1973, 23, 209-261.
27. See review, Y. Chao, D. J. Cram, J. Am. Chem. Soc. 1976, 98, 1015-1017.
28. H. Durr, H. Bouas-Laurent, Photochromism: Molecules and systems, Elsevier: Amsterdam, 2003.
29. R. S. Givens, C.-H. Park, Tetrahedron Lett. 1996, 37, 6259-6262.
30. C.-H. Park, R. S. Givens, J. Am. Chem. Soc. 1997, 119, 2453-2463.
31. R. Y. Tsien, R. S. Zucker, Biophys. J. 1986, 50, 843-853.
32. J. H. Kaplan, G. C. R. Ellis-Davies, Proc. Natl. Acad. Sci. U. S. A. 1988, 85, 6571-6575.
33. M. M. Martin, P. Plaza, Y. H. Meyer, F. Badaoui, J. Bourson, J.-P. Lefevre, B. Valeur, J. Phys. Chem. 1996, 100, 6879-6888.
34. K. Ohkubo, S. Fukuzumi, Bull. Chem. Soc. Jpn. 2009, 82, 303-315.
35. O. Sadovski, A. A. Beharry, F. Zhang, G. A. Woolley, Angew. Chem. Int. Ed. 2009, 48, 1484-1486.
36. G. Berkovic, V. Krongauz, V. Weiss, Chem. Rev. 2000, 100, 1741-1753.
37. V. I. Minkin, Chem. Rev. 2004, 104, 2751-2776.
38. Y. Yokoyama, in Molecular switches, (Eds:, B. L. Feringa,) Wiley-VCH: Weinheim, 2001.
39. H. Tian, S. Yang, Chem. Soc. Rev. 2004, 33, 85-97.
40. S. Shinkai, T. Nakaji, T. Ogawa, K. Shigematsu, O. Manabe, J. Am. Chem. Soc. 1981, 103, 111-115.
41. M. Takeshita, M. Irie, J. Org. Chem. 1998, 63, 6643-6649.
42. S. H. Kawai, Tetrahedron Lett. 1998, 39, 4445-4448.
43. D. J. Cram, Angew. Chem. Int. Ed Engl. 1986, 25, 1039-1134.
44. R. Hoffmann, Chem. Eng. News 1974, July 29, 32-34.
45. A. Bencini, A. Bianchi, C. Giorgi, E. Romagnoli, C. Lodeiro, A. Saint-Maurice, F. Pina, B. Valtancoli, Supramol. Chem. 2001, 13, 277-285.
46. "Tweezer-like" is a descriptor suggested by one of the referees. Molecular tweezers are defined as "synthetic molecular receptors with an open cavity defined by two interaction sites for substrate binding, bridged by a spacer"; see, J. Leblond, A. Petitjean, Chemphyschem 2011, 12, 1043-4051.
47. Foldamer, is an alternative description of the receptors considered in this section. However, the use of foldamer is debatable when considering the definition put forth by J. S. Moore that a foldamer is "any oligomer that folds into a conformationally ordered state"; see, D. J. Hill, M. J. Mio, R. B. Prince, T. S. Hughes, J. S. Moore, Chem. Rev. 2001, 101, 3893-4011.
48. T. Shimasaki, S.-i. Kato, K. Ideta, K. Goto, T. Shinmyozu, J. Org. Chem. 2007, 72, 1073-1087.
49. Y. Wang, F. Bie, H. Jiang, Org. Lett. 2010, 12, 3630-3633.
50. Y. Hua, A. H. Flood, Chem. Soc. Rev. 2010, 39, 1262-1271.
51. K. P. McDonald, Y. Hua, A. H. Flood, Top. Heterocycl. Chem. 2010, 24, 341-366.
52. Z. Li, C. Zhang, Y. Ren, J. Yin, S. H. Liu, Org. Lett. 2011, 13, 6022-6025.
53. A. Khan, C. Kaiser, S. Hecht, Angew. Chem. Int. Ed. 2006, 45, 1878-1881.
54. A. Khan, S. Hecht, Chem. Eur. J. 2006, 12, 4764-4774.
55. Z. Yu, S. Hecht, Angew. Chem. Int. Ed. 2011, 50, 1640-1643.
56. Y. Wang, F. Li, Y. Han, F. Wang, H. Jiang, Chem. Eur. J. 2009, 15, 9424-9433.
57. C. Tie, J. C. Callucci, J. R. Parquette, J. Am. Chem. Soc. 2006, 128, 1162-1171.
58. E. D. King, P. Tao, T. T. Sanan, C. M. Hadad, J. R. Parquette, Org. Lett. 2008, 10, 1671-1674.
59. J. C. Nelson, J. G. Saven, J. S. Moore, P. G. Wolynes, Science 1997, 277, 1793-1796.
60. M. T. Stone, J. M. Heemstra, J. S. Moore, Acc. Chem. Res. 2006, 39, 11-20.
61. Y. Li, A. H. Flood, Angew. Chem. Int. Ed. 2008, 47, 2649-2652.
62. Y. Li, A. H. Flood, J. Am. Chem. Soc. 2008, 130, 12111-12122.
63. H. Juwarker, J. M. Lenhardt, D. M. Pham, S. L. Craig, Angew. Chem. Int. Ed. 2008, 47, 3740-3743.
64. R. M. Meudtner, S. Hecht, Angew. Chem. Int. Ed. 2008, 47, 4926-4930.
65. Y. Hua, A. H. Flood, J. Am. Chem. Soc. 2010, 132, 12838-12840.
66. T. Nakashima, R. Fujii, T. Kawai, Chem. Eur. J. 2011, 17, 10951-10957.