Application of the ΔΛ isomerism of octahedral metal complexes as a chiral source in photochemistry

Journal of Photochemistry and Photobiology C: Photochemistry Reviews

Volumn 8, Issue 2, 2007, Pages 67-84

  Sato, Hisako ^a,b   Yamagishi, Akihiko ^b,c  

^a UNIVERSITY OF TOKYO   (Japan)

^b JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

^c OCHANOMIZU UNIVERSITY   (Japan)

Author keywords

isomerism; Asymmetric reaction; Azo compounds; Catalysis; Chiral metal complexes; Chiral sensor; Clay minerals; Cyclodextrin; DNA; Fluorescence; Liquid crystal; Monolayer; Photochemistry; Photoisomerization; Photooxidation; Photoracemization; Photosensitizer; Sulfide

Indexed keywords

CATALYSIS; CHIRALITY; CLAY MINERALS; DNA; FLUORESCENCE; LIQUID CRYSTALS; MONOLAYERS; PHOTOISOMERIZATION; PHOTOOXIDATION; PHOTOSENSITIZERS;

ASYMMETRIC REACTIONS; AZO COMPOUNDS; CHIRAL METAL COMPLEXES; CHIRAL SENSORS; CYCLODEXTRIN; PHOTORACEMIZATION; SULFIDES;

METAL COMPLEXES;

EID: 34547683171     PISSN: 13895567     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jphotochemrev.2007.04.001     Document Type: Review

References (134)

1. Werner A. Chem. Ber. 44 (1911) 1887
2. Pierre J.L. Coord. Chem. Rev. 180 (1998) 1183-1192
3. Knight P.D., and Scott P. Coord. Chem. Rev. 242 (2003) 125-143
4. Knof U., and von Zelewsky A. Angew. Chem. Int. Ed. 38 (1999) 303-322
5. von Zelewsky A., Belser P., Hayoz P., Dux R., Hua X., Suckling A., and Stoecklievans H. Coord. Chem. Rev. 132 (1994) 75-85
6. Belser P., Bernhard S., Jandrasics E., von Zelewsky A., DeCola L., and Balzani V. Coord. Chem. Rev. 159 (1997) 1-8
7. Miyake H., Yoshida K., Sugimoto H., and Tsukube H. J. Am. Chem. Soc. 126 (2004) 6524-6525
8. Biscarini P., Benedetti M., Kuroda R., and Ferranti F. Eur. J. Inorg. Chem. (2006) 3167-3176
9. Ohkubo K., Hamada T., and Ishida H. J. Chem. Soc. Chem. Commun. (1993) 1423-1425
10. Hamada T., Ishida H., Usui S., Watanabe Y., Tsumura K., and Ohkubo K. J. Chem. Soc. Chem. Commun. (1993) 909-911
11. Ohkubo K., and Ishida H. J. Syn. Org. Chem. Jpn. 50 (1992) 234-243
12. Ohkubo K., Hamada T., Inaoka T., and Ishida H. Inorg. Chem. 28 (1989) 2021-2022
13. Ohkubo K., Watanabe M., Ohta H., and Usui S. J. Photochem. Photobiol. A: Chem. 95 (1996) 231-233
14. Ohkubo K., Hamada T., Ishida H., Fukushima M., and Watanabe M. J. Mol. Catal. 89 (1994) L5-L10
15. Sakaki S., Ishikura H., Kuraki K., Tanaka K., Satoh T., Arai T., and Hamada T. J. Chem. Soc., Dalton Trans. (1997) 1815-1820
16. Hamada T., Brunschwig B.S., Eifuku K., Fujita E., Korner M., Sakaki S., van Eldik R., and Wishart J.F. J. Phys. Chem. A 103 (1999) 5645-5654
17. Ishida H., Hamada T., Fujishita Y., Saito Y., and Ohkubo K. Bull. Chem. Soc. Jpn. 66 (1993) 714-720
18. Kyakuno M., Oishi S., and Ishida H. Inorg. Chem. 45 (2006) 3756-3765
19. Browne W.R., Hesek D., Gallagher J.F., O'Connor C.M., Killeen J.S., Aoki F., Ishida H., Inoue Y., Villani C., and Vos J.G. Dalton Trans. (2003) 2597-2602
20. Hesek D., Hembury G.A., Drew M.G.B., Taniguchi S., and Inoue Y. Inorg. Chem. 40 (2001) 2478-2479
21. Kawasaki T., Sato M., Ishiguro S., Saito T., Morishita Y., Sato I., Nishino H., Inoue Y., and Soai K. J. Am. Chem. Soc. 127 (2005) 3274-3275
22. Barron J.A., Glazier S., Bernhard S., Takada K., Houston P.L., and Abruna H.D. Inorg. Chem. 42 (2003) 1448-1455
23. Drahonovsky D., Knof U., Jungo L., Belser T., Neels A., Labat G.C., Stoeckli-Evans H., and von Zelewsky A. Dalton Trans. (2006) 1444-1454
24. Hamann C.S., von Zelewsky A., Barbieri A., Barigelletti F., Muller G., Riehl J.P., and Neels A. J. Am. Chem. Soc. 126 (2004) 9339-9348
25. Hamann C., von Zelewsky A., Neels A., and Stoeckli-Evans H. Dalton Trans. (2004) 402-406
26. Karatsu T., Ito E., Yagai S., and Kitamura A. Chem. Phys. Lett. 424 (2006) 353-357
27. Yamagishi A., Naing K., Goto Y., Taniguchi M., and Takahashi M. J. Chem. Soc., Dalton Trans. (1994) 2085-2089
28. Rutherford T.J., Pellegrini P.A., Aldrich-Wright J., Junk P.C., and Keene F.R. Eur. J. Inorg. Chem. (1998) 1677-1688
29. Chandrasekhar V., Azhakar R., Zacchini S., Bickley J.F., and Steiner A. Inorg. Chem. 44 (2005) 4608-4615
30. Bassett A.P., Magennis S.W., Glover P.B., Lewis D.J., Spencer N., Parsons S., Williams R.M., De Cola L., and Pikramenou Z. J. Am. Chem. Soc. 126 (2004) 9413-9424
31. Muller G., Riehl J.P., Schenk K.J., Hopfgartner G., Piguet C., and Bunzli J.C.G. Eur. J. Inorg. Chem. (2002) 3101-3110
32. Muller G., Schmidt B., Jiricek J., Hopfgartner G., Riehl J.P., Bunzli J.C.G., and Piguet C. J. Chem. Soc., Dalton Trans. (2001) 2655-2662
33. Fletcher N.C., Nieuwenhuyzen M., and Rainey S. J. Chem. Soc., Dalton Trans. (2001) 2641-2648
34. Fan Q.H., Li Y.M., and Chan A.S.C. Chem. Rev. 102 (2002) 3385-3465
35. Trost B.M. Science 254 (1991) 1471-1477
36. Orito Y., Imai S., and Niwa S. Nippon Kagaku Kaishi (1979) 1118-1120
37. Yamagishi A. J. Coord. Chem. 16 (1987) 131-211
38. Shichi T., and Takagi K. J. Photochem. Photobiol. C: Photochem. Rev. 1 (2000) 113-130
39. Thomas J.K. Acc. Chem. Res. 21 (1988) 275-280
40. Dellaguardia R.A., and Thomas J.K. J. Phys. Chem. 87 (1983) 990-998
41. Chu D.Y., and Thomas J.K. J. Phys. Chem. 89 (1985) 4065-4070
42. Ghosh P.K., and Bard A.J. J. Phys. Chem. 88 (1984) 5519-5526
43. Joshi V., and Ghosh P.K. J. Am. Chem. Soc. 111 (1989) 5604-5612
44. Kamat P.V., Gopidas K.R., Mukherjee T., Joshi V., Kotkar D., Pathak V.S., and Ghosh P.K. J. Phys. Chem. 95 (1991) 10009-10018
45. Kamat P.V. Chem. Rev. 93 (1993) 267-300
46. Yamagishi A., and Soma M. J. Am. Chem. Soc. 103 (1981) 4640-4642
47. Yamagishi A. J. Chem. Soc. Chem. Commun. (1984) 119-120
48. Yamagishi A. J. Am. Chem. Soc. 107 (1985) 732-734
49. Yamagishi A. J. Chem. Soc. Chem. Commun. (1986) 290-291
50. Taniguchi M., Yamagishi A., and Iwamoto T. Inorg. Chem. 30 (1991) 2462-2467
51. Sato H., Hiroe Y., Tamura K., and Yamagishi A. J. Phys. Chem. B 109 (2005) 18935-18941
52. Sato H., Yamagishi A., and Kato S. J. Am. Chem. Soc. 114 (1992) 10933-10940
53. Sato H., Yamagishi A., Naka K., and Kato S. J. Phys. Chem. 100 (1996) 1711-1717
54. Sato H., Yamagishi A., and Kato S. J. Phys. Chem. 96 (1992) 9377-9382
55. Sato H., Yamagishi A., and Kato S. J. Phys. Chem. 96 (1992) 9382-9387
56. Hikita T., Tamaru K., Yamagishi A., and Iwamoto T. Inorg. Chem. 28 (1989) 2221-2223
57. Fujita S., Sato H., Kakegawa N., and Yamagishi A. J. Phys. Chem. B 110 (2006) 2533-2540
58. Mallouk T.E., and Gavin J.A. Acc. Chem. Res. 31 (1998) 209-217
59. Umemura Y., and Shinohara E. Chem. Commun. (2004) 1110-1111
60. Breu J., Stoll A., Lange K.G., and Probst T. Phys. Chem. Chem. Phys. 3 (2001) 1232-1235
61. Wakabayashi N., Nishimura S.-I., Kakegawa N., Sato H., and Yamagishi A. Clay Sci. 12 (2004) 259-266
62. Das P., Kuzniarska-Biernacka I., Silva A.R., Carvalho A.P., Pires J., and Freire C. J. Mol. Catal. A: Chem. 248 (2006) 135-143
63. Barton J.K., and Raphael A.L. J. Am. Chem. Soc. 106 (1984) 2466-2468
64. Kumar C.V., Barton J.K., and Turro N.J. J. Am. Chem. Soc. 107 (1985) 5518-5523
65. Pyle A.M., Long E.C., and Barton J.K. J. Am. Chem. Soc. 111 (1989) 4520-4522
66. Krotz A.H., Kuo L.Y., Shields T.P., and Barton J.K. J. Am. Chem. Soc. 115 (1993) 3877-3882
67. Sitlani A., Dupureur C.M., and Barton J.K. J. Am. Chem. Soc. 115 (1993) 12589-12590
68. Dupureur C.M., and Barton J.K. Inorg. Chem. 36 (1997) 33-43
69. Stemp E.D.A., Arkin M.R., and Barton J.K. J. Am. Chem. Soc. 119 (1997) 2921-2925
70. Junicke H., Hart J.R., Kisko J., Glebov O., Kirsch I.R., and Barton J.K. Proc. Natl. Acad. Sci. U.S.A. 100 (2003) 3737-3742
71. Zeglis B.M., and Barton J.K. J. Am. Chem. Soc. 128 (2006) 5654-5655
72. Pierre V.C., Kaiser J.T., and Barton J.K. Proc. Natl. Acad. Sci. U.S.A. 104 (2007) 429-434
73. Liang M.M., Liu S.L., Wei M.Y., and Guo L.H. Anal. Chem. 78 (2006) 621-623
74. Naing K., Takahashi M., Taniguchi M., and Yamagishi A. J. Chem. Soc. Chem. Commun. (1993) 402-403
75. Naing K., Takahashi M., Taniguchi M., and Yamagishi A. Inorg. Chem. 34 (1995) 350-356
76. Mesmaeker A.K.D., Moucheron C., and Boutonnet N. J. Phys. Org. Chem. 11 (1998) 566-576
77. Kane-Maguire N.A.P., and Wheeler J.F. Coord. Chem. Rev. 211 (2001) 145-162
78. Ossipov D., Gohil S., and Chattopadhyaya J. J. Am. Chem. Soc. 124 (2002) 13416-13433
79. Yang P., Han D.X., and Xiong Z.H. J. Mol. Struct. Theochem 540 (2001) 211-219
80. Mahnken R.E., Billadeau M.A., Nikonowicz E.P., and Morrison H. J. Am. Chem. Soc. 114 (1992) 9253-9265
81. Chauhan M., and Arjmand F. Chem. Biodivers. 3 (2006) 660-676
82. Sivaguru J., Poon T., Franz R., Jockusch S., Adam W., and Turro N.J. J. Am. Chem. Soc. 126 (2004) 10816-10817
83. Sivaguru J., Saito H., Solomon M.R., Kaanumalle L.S., Poon T., Jockusch S., Adam W., Ramamurthy V., Inoue Y., and Turro N.J. Photochem. Photobiol. 82 (2006) 123-131
84. Hesek D., Hembury G.A., Drew M.G.B., Borovkov V.V., and Inoue Y. J. Am. Chem. Soc. 123 (2001) 12232-12237
85. Nakamura A., and Inoue Y. J. Am. Chem. Soc. 127 (2005) 5338-5339
86. Nishiyama H., Naitoh T., Motoyama Y., and Aoki K. Chem. Eur. J. 5 (1999) 3509-3513
87. Drake A.F., Gottarelli G., and Spada G.P. Chem. Phys. Lett. 110 (1984) 630-633
88. Matsuoka Y., Sato H., Yamagishi A., Okamoto K., and Hoshino N. Chem. Mater. 17 (2005) 4910-4917
89. Sato H., Yamagishi A., Yoshida J., Nakano H., and Hoshino N. Jpn. J. Appl. Phys., Part 1 44 (2005) 4067-4072
90. Yoshida J., Sato H., Yamagishi A., and Hoshino N. J. Am. Chem. Soc. 127 (2005) 8453-8456
91. Hoshino N., Matsuoka Y., Okamoto K., and Yamagishi A. J. Am. Chem. Soc. 125 (2003) 1718-1719
92. Huck N.P.M., Jager W.F., deLange B., and Feringa B.L. Science 273 (1996) 1686-1688
93. Trzaska S.T., Hsu H.F., and Swager T.M. J. Am. Chem. Soc. 121 (1999) 4518-4519
94. Ikeda Y., Imae T., Iida M., Koine N., and Kaizaki S. Langmuir 17 (2001) 361-368
95. Binnemans K., and Gorller-Walrand C. Chem. Rev. 102 (2002) 2303-2345
96. Yutaka T., Mori I., Kurihara M., Mizutani J., Kubo K., Furusho S., Matsumura K., Tamai N., and Nishihara H. Inorg. Chem. 40 (2001) 4986-4995
97. Ikeda T. J. Mater. Chem. 13 (2003) 2037-2057
98. Eelkema R., and Feringa B.L. Org. Biomol. Chem. 4 (2006) 3729-3745
99. Anzai N., Machidat S., and Horie K. Liq. Cryst. 30 (2003) 359-366
100. Anzai N., Kurihara H., Sone M., Furukawa H., Watanabe T., Horie K., and Kumar S. Liq. Cryst. 33 (2006) 671-679
101. Anzai, Machida S., and Horie K. Chem. Lett. (2001) 888-889
102. Furuno Y., Sato H., Yoshida J., Hoshino N., Fukuda Y., and Yamagishi A. J. Phys. Chem. B 111 (2007) 521-526
103. Mitsuoka T., Sato H., Yoshida J., Yamagishi A., and Einaga Y. Chem. Mater. 18 (2006) 3442-3447
104. Taniguchi T., Monde K., Nishimura S.I., Yoshida J., Sato H., and Yamagishi A. Mol. Cryst. Liq. Cryst. 460 (2006) 107-116
105. Sato H., Taniguchi T., Monde K., Nishimura S.I., and Yamagishi A. Chem. Lett. 35 (2006) 364-365
106. Stine K.J., Uang J.Y.J., and Dingman S.D. Langmuir 9 (1993) 2112-2118
107. Nielsen M., Larsen N.B., and Gothelf K.V. Langmuir 18 (2002) 2795-2799
108. de Feyter S., and de Schryver F.C. J. Phys. Chem. B 109 (2005) 4290-4302
109. Belser T., Stohr M., and Pfaltz A. J. Am. Chem. Soc. 127 (2005) 8720-8731
110. Xu X.H., Yang H.C., Mallouk T.E., and Bard A.J. J. Am. Chem. Soc. 116 (1994) 8386-8387
111. Suzuki M., Waraksa C.C., Mallouk T.E., Nakayama H., and Hanabusa K. J. Phys. Chem. B 106 (2002) 4227-4231
112. Hara M., Lean J.T., and Mallouk T.E. Chem. Mater. 13 (2001) 4668-4675
113. Culp J.T., Park J.H., Stratakis D., Meisel M.W., and Talham D.R. J. Am. Chem. Soc. 124 (2002) 10083-10090
114. Talham D.R. Chem. Rev. 104 (2004) 5479-5501
115. Albrecht T., Guckian A., Kuznetsov A.M., Vos J.G., and Ulstrup J. J. Am. Chem. Soc. 128 (2006) 17132-17138
116. Taniguchi M., Ueno N., Okamoto K., Karthaus O., Shimomura M., and Yamagishi A. Langmuir 15 (1999) 7700-7707
117. Okamoto K., Takahashi M., Taniguchi M., and Yamagishi A. Chem. Lett. (2000) 740-741
118. Okamoto K., Taniguchi M., Takahashi M., and Yamagishi A. Langmuir 17 (2001) 195-201
119. Inukai K., Hotta Y., Tomura S., Takahashi M., and Yamagishi A. Langmuir 16 (2000) 7679-7684
120. Umemura Y., Yamagishi A., Schoonheydt R., Persoons A., and De Schryver F. J. Am. Chem. Soc. 124 (2002) 992-997
121. He J.X., Sato H., Yang P.J., and Yamagishi A. J. Electroanal. Chem. 560 (2003) 169-174
122. He J.X., Sato H., Umemura Y., and Yamagishi A. J. Phys. Chem. B 109 (2005) 4679-4683
123. Tamura K., Sato H., Yamashita S., Yamagishi A., and Yamada H. J. Phys. Chem. B 108 (2004) 8287-8293
124. Takahashi S., Tanaka R., Wakabayashi N., Taniguchi M., and Yamagishi A. Langmuir 19 (2003) 6122-6125
125. Kashiwara S., Takahashi M., Nakata M., Taniguchi M., and Yamagishi A. J. Mater. Chem. 8 (1998) 2253-2257
126. Yamagishi A., Sasa N., Taniguchi M., Endo A., Sakamoto M., and Shimizu K. Langmuir 13 (1997) 1689-1694
127. Inose Y., Moniwa S., Aramata A., Yamagishi A., and Naing K. Chem. Commun. (1997) 111-112
128. Tamura K., Setsuda H., Taniguchi M., and Yamagishi A. Langmuir 15 (1999) 6915-6920
129. Goto Y., Takahashi M., Taniguchi M., and Yamagishi A. J. Chem. Soc. Chem. Commun. (1994) 1299
130. Yamagishi A., Goto Y., and Taniguchi M. J. Phys. Chem. 100 (1996) 1827-1832
131. Kakegawa N., Hoshino N., Matsuoka Y., Wakabayashi N., Nishimura S.I., and Yamagishi A. Chem. Commun. (2005) 2375-2377
132. Hotta Y., Inukai K., Taniguchi M., Nakata M., and Yamagishi A. Langmuir 13 (1997) 6697-6703
133. Kobayashi K., Sato H., Kishi S., Kato M., Ishizaka S., Kitamura N., and Yamagishi A. J. Phys. Chem. B 108 (2004) 18665-18669
134. Kawamata J., Ogata Y., Taniguchi M., Yamagishi A., and Inoue K. Mol. Cryst. Liq. Cryst. 343 (2000) 371-376