Photoinduced rearrangements in transition metal compounds

Coordination Chemistry Reviews

Volumn 254, Issue 21-22, 2010, Pages 2519-2532

  Vos, Johannes G ^a   Pryce, Mary T ^a  

^a DUBLIN CITY UNIVERSITY   (Ireland)

Author keywords

Isomerisation rearrangements; Organometallic; Photocatalytic; Photochemistry; Transition metal

Indexed keywords

EID: 77956226794     PISSN: 00108545     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ccr.2010.04.010     Document Type: Review

References (175)

1. Adamson A.W. J. Phys. Chem. 1967, 77:798.
2. Adamson A.W. Advances in Chemistry Series, No. 49 1965, American Chemical Society, Washington, DC.
3. Vanquickenborne L.G., Ceulemans A. J. Am. Chem. Soc. 1977, 99:2208.
4. Sprintschnik G., Sprintschnik H.W., Kirsch P.P., Whitten D.G. J. Am. Chem. Soc. 1976, 98:2337.
5. Sprintschnik G., Sprintschnik H.W., Kirsch P.P., Whitten D.G. J. Am. Chem. Soc. 1977, 99:4949.
6. Balzani V., Juris A., Venturi M., Campagna S., Serroni S. Chem. Rev. 1996, 96:759.
7. De Cola L., Belser P. Coord. Chem. Rev. 1998, 177:301.
8. Balzani V., Scandola F. Supramolecular Photochemistry 1991, Ellis Horwood, New York.
9. Vos J.G., Kelly J.M. Dalton Trans. 2006, 4869.
10. O'Regan B., Grätzel M. Nature 1991, 353:737.
11. Hagfeldt A., Grätzel M. Acc. Chem. Res. 2000, 33:269.
12. Baranoff E., Yum J.-H., Grätzel M., Nazeeruddin Md.K. J. Organomet. Chem. 2009, 694:2661.
13. Flamigni L., Collin J.-P., Sauvage J.-P. Acc. Chem. Res. 2008, 41:857.
14. Coleman A., Brennan C., Vos J.G., Pryce M.T. Coord. Chem. Rev. 2008, 252:2585.
15. Kirgan R.A., Sullivan B.P., Rillema D.P. Top. Curr. Chem. 2007, 281:45.
16. Vlček A., Záliš S. Coord. Chem. Rev. 2007, 251:258.
17. Polo A.S., Itokazu M.K., Frin K.M., de Toledo Patrocínio A.O., Iha N.Y.M. Coord. Chem. Rev. 2006, 250:1669.
18. Degani Y., Heller A. J. Am. Chem. Soc. 1989, 111:2367.
19. Heller A. Acc. Chem. Res. 1990, 23:128.
20. Heller A. J. Phys. Chem. 1992, 96:3567.
21. Aoki A., Heller A. J. Phys. Chem. 1993, 97:11014.
22. Doherty A.P., Stanley M.A., Leech D., Vos J.G. Anal. Chim. Acta 1996, 319:111.
23. Doherty A.P., Vos J.G. J. Chem. Soc., Faraday Trans. 1992, 88:2903.
24. Doherty A.P., Stanley M.A., Vos J.G. Analyst 1995, 120:2371.
25. Albrecht T., Guckian A., Ulstrup J., Vos J.G. Nano Lett. 2005, 5:1451.
26. Albrecht T., Guckian A., Ulstrup J., Vos J.G. IEEE Trans. Nanotechnol. 2005, 4:430.
27. Albrecht T., Moth-Poulsen K., Christensen J.B., Guckian A., Bjornholm T., Vos J.G., Ulstrup J. Faraday Discuss. 2006, 131:265.
28. Bechman R., Beverly K., Boukai A., Bunimovich Y., Choi J.W., DeIonno E., Green J., Johnston-Halperin E., Luo Y., Sheriff B., Stoddart J.F., Heath J.R. Faraday Discuss. 2006, 131:9.
29. Mallins C., Fanni S., Glever H.G., Vos J.G., MacCraith B.D. Anal. Commun. 1999, 36:3.
30. Lobnik A., Oehme I., Murkovic I., Wolfbeis O.S. Anal. Chim. Acta 1998, 367:159.
31. Demas J.N., DeGraff B.A. J. Chem. Educ. 1997, 74:690.
32. Chou P.-T., Chi Y. Chem. Eur. J. 2007, 13:380.
33. Inomata H., Goushi K., Masuko T., Konno T., Imai T., Sasabe H., Brown J.J., Adachi C. Chem. Mater. 2004, 16:1285.
34. Yamamoto H., Wilkinson J., Long J.P., Bussman K., Christodoulides J.A., Kafafi Z.H. Nano Lett. 2005, 5:2485.
35. Balzani V. Small 2005, 1:278.
36. Bazani V., Venturi M., Credo A. Molecular Devices and Machines 2003, Wiley-VCH, Weinheim.
37. Sauvage J.P. Acc. Chem. Res. 1998, 31:611.
38. Collin J.P., Heitz V., Bonnet S., Sauvage J.-P. Inorg. Chem. Commun. 2005, 8:1063.
39. Barton J.K., Danishefsky A.T., Goldberg J.M. J. Am. Chem. Soc. 1984, 106:2172.
40. Barton J.K., Goldberg J.M., Kumar C.V., Turro N.J. J. Am. Chem. Soc. 1986, 108:2081.
41. Kelly J.M., Tossi A.B., McConnell D.J., OhUigin C. Nucleic Acids Res. 1985, 13:6017.
42. Jacquet L., Kelly J.M., Kirsch-De Mesmaeker A. J. Chem. Soc., Chem. Commun. 1995, 913.
43. Jacquet L., Davies R.J.H., Kirsch-De Mesmaeker A., Kelly J.M. J. Am. Chem. Soc. 1997, 119:11763.
44. Wilhelmsson L.M., Westerlund F., Lincoln P., Norden B. J. Am. Chem. Soc. 2002, 124:12092.
45. Steinberg-Yfrach G., Rigaud J.-L., Durantini E.N., Moore A.L., Gust D., Moore T.A. Nature 1998, 392:479.
46. Koumura N., Zijlstra R.W.J., van Delden R.A., Harada N., Feringa B.L. Nature 1999, 401:152.
47. Armaroli N., Balzani V., Collin J.-P., Gavina P., Sauvage J.-P., Ventura B. J. Am. Chem. Soc. 1999, 121:4397.
48. Champin B., Mobian P., Sauvage J.-P. Chem. Soc. Rev. 2007, 36:358.
49. Balzani V., Clemente-Leon M., Credi A., Ferrer B., Venturi M., Flood A.H., Stoddart J.F. Proc. Natl. Acad. Sci. U.S.A. 2006, 103:1178.
50. Balzani V., Bergamini G., Ceroni P. Coord. Chem. Rev. 2008, 252:2456.
51. Rau S., Walther D., Vos J.G. Dalton Trans. 2007, 915. and references therein.
52. Gersten S.W., Samuels G.J., Meyer T.J. J. Am. Chem. Soc. 1982, 104:4029.
53. Doppelt P., Meyer T.J. Inorg. Chem. 1987, 26:2027.
54. Ishitani O., White P.S., Meyer T.J. Inorg. Chem. 1996, 35:2167.
55. Yagi M., Syouji A., Yamada S., Komi M., Yamazaki H., Tajima S. Photochem. Photobiol. Sci. 2009, 8:139.
56. Takeda H., Koike K., Inoue H., Ishitani O. J. Am. Chem. Soc. 2008, 130:2023.
57. Hayashi Y., Kita S., Brunschwig B.S., Fujita E. J. Am. Chem. Soc. 2003, 125:11976.
58. Hawecker J., Lehn J.-M., Ziessel R. Helv. Chim. Acta 1986, 69:1990.
59. Takeda H., Ishitani O. Coord. Chem. Rev. 2010, 254:346.
60. Fujita E. Coord. Chem. Rev. 1999, 185-186:373.
61. Morris A.J., Meyer G.J., Fujita E. Acc. Chem. Res. 2009, 42:1983.
62. McQuillin F.J., Parker D.G., Stephenson G.R. Transition Metal Organometallics for Organic Synthesis 1991, Cambridge University Press, Cambridge, UK.
63. Yam V.W.-W., Ko C.-C., Zhu N.Y. J. Am. Chem. Soc. 2004, 126:12734.
64. Kume S., Nishihara H. Dalton Trans. 2008, 3260.
65. Ko C.-C., Kwok W.-M., Yam V.W.W., Phillips D.L. Chem. Eur. J. 2006, 12:5840.
66. Roberts M.N., Nagle J.K., Finden J.G., Branda N.R., Wolf M.O. Inorg. Chem. 2009, 48:19.
67. Molecular Switches 2001, Wiley VCH, Weinheim. B.L. Feringa (Ed.).
68. ter Wiel M.K.J., van Delden R.A., Meetsma A., Feringa B.L. J. Am. Chem. Soc. 2005, 127:14208.
69. Belser P., Bernhard S., Blum C., Beyeler A., De Cola L., Balzani V. Coord. Chem. Rev. 1999, 192:155.
70. Rack J.J. Coord. Chem. Rev. 2009, 253:78.
71. Sullivan B.P., Meyer T.J. Inorg. Chem. 1982, 21:1037.
72. Durham B., Caspar J.V., Nagle J.K., Meyer T.J. J. Am. Chem. Soc. 1982, 104:4803.
73. Durham B., Walsh J.L., Carter C.L., Meyer T.J. Inorg. Chem. 1980, 19:860.
74. Tachiyashiki S., Ikezawa H., Mizumachi K. Inorg. Chem. 1994, 33:623.
75. Clear J.M., Kelly J.M., O'Connell C.M., Vos J.G., Cardin C.J., Costa S.R., Edwards A.J. J. Chem. Soc., Chem. Commun. 1980, 750.
76. Kelly J.M., O'Connell C.M., Vos J.G. J. Chem. Soc., Dalton Trans. 1986, 253.
77. Kelly J.M., Vos J.G. Angew. Chem. Int. Ed. Engl. 1982, 94:644.
78. Kelly J.M., Vos J.G. J. Chem. Soc., Dalton Trans. 1986, 1045.
79. Haasnoot J.G., Hinrichs W., Weir O., Vos J.G. Inorg. Chem. 1986, 25:4140.
80. Lehn J.-M., Ziessel R. J. Organomet. Chem. 1990, 382:157.
81. Chardon-Noblat S., Deronzier A., Ziessel R., Zsoldos D. J. Electrochem. Chem. 1998, 444:253.
82. Ford P.C. Acc. Chem. Res. 1981, 14:31.
83. Ishida H., Tanaka K., Morimoto M., Tanaka T. Organometallics 1986, 5:724.
84. Buchanan B.E., McGovern E., Harkin P., Vos J.G. Inorg. Chim. Acta 1988, 154.
85. Hecker C.R., Fanwick P.E., McMillin D.R. Inorg. Chem. 1991, 30:659.
86. Mobian P., Kern J.-M., Sauvage J.-P. Angew. Chem. Int. Ed. 2004, 43:2392.
87. Koike K., Okoshi N., Hori H., Takeuchi K., Ishitani O., Tsubaki H., Clark I.P., George M.W., Johnson F.P.A., Turner J.J. J. Am. Chem. Soc. 2002, 124:11448.
88. Koike K., Tanabe J., Toyama S., Tsubaki H., Sakamoto K., Westwell J.R., Johnson F.P.A., Hori H., Saitoh H., Ishitani O. Inorg. Chem. 2000, 39:2777.
89. Juris A., Balzani V., Barigelletti F., Campagna S., Belser P., von Zelewsky A. Coord. Chem. Rev. 1988, 82:85.
90. Meyer T.J. Pure Appl. Chem. 1986, 58:1193.
91. Davila J., Bignozzi C.A., Scandola F. J. Phys. Chem. 1989, 93:1373.
92. Sato S., Sekine A., Ohashi Y., Ishitani O., Blanco-Rodri{dotless}guez A.M., Vlcek A., Unno T., Koike K. Inorg. Chem. 2007, 46:3531.
93. Durham B., Wilson S.R., Hodgson D.J., Meyer T.J. J. Am. Chem. Soc. 1980, 102:600.
94. Tamayo A.B., Alleyne B.D., Djurovich P.I., Lamansky S., Tsyba I., Ho N.N., Bau R., Thompson M.E. J. Am. Chem. Soc. 2003, 125:7377.
95. Karatsu T., Ito E., Yagai S., Kitamura A. Chem. Phys. Lett. 2006, 424:353.
96. Tsuchiya K., Ito E., Yagai S., Kitamura A., Karatsu T. Eur. J. Inorg. Chem. 2009, 2104.
97. Sato S., Morimoto T., Ishitani O. Inorg. Chem. 2007, 46:9051.
98. Hesek D., Hembury G.A., Drew M.G.B., Taniguchi S., Inoue Y. J. Am. Chem. Soc. 2000, 122:10236.
99. Ciofini I., Daul C.A., Adamo C. J. Phys. Chem. A 2003, 107:11182.
100. Hage R., Haasnoot J.G., Nieuwenhuis H.A., Reedijk J., De Ridder D.J.A., Vos J.G. J. Am. Chem. Soc. 1990, 112:9245.
101. De Cola L., Barigelletti F., Balzani V., Hage R., Haasnoot J.G., Reedijk J., Vos J.G. Chem. Phys. Lett. 1991, 178:491.
102. Nieuwenhuis H.A., Haasnoot J.G., Hage R., Reedijk J., Snoeck T.L., Stufkens D.J., Vos J.G. Inorg. Chem. 1991, 30:48.
103. Fanni S., Keyes T.E., O'Connor C.M., Hughes H., Wang R., Vos J.G. Coord. Chem. Rev. 2000, 208:77.
104. Wang R., Vos J.G., Schmehl R.H., Hage R. J. Am. Chem. Soc. 1992, 114:1964.
105. Fanni S., Weldon F.M., Hammarström L., Mukhtar E., Browne W.R., Keyes T.E., Vos J.G. Eur. J. Inorg. Chem. 2001, 529.
106. Fanni S., Murphy S., Killeen J.S., Vos J.G. Inorg. Chem. 2000, 39:1320.
107. Buchanan B.E., Hughes H., van Diemen J., Hage R., Haasnoot J.G., Reedijk J., Vos J.G. J. Chem. Soc., Chem. Commun. 1991, 300.
108. Buchanan B.E., Hughes H., Degn P., Pavon Velasco J.M., Creaven B.S., Long C., Vos J.G., Howie R.A., Hage R., van Diemen J.H., Haasnoot J.G., Reedijk J. J. Chem. Soc., Dalton Trans. 1992, 1177.
109. Bonnet S., Collin J.-P., Sauvage J.-P. Inorg. Chem. 2007, 46:10520.
110. Miyazaki S., Koyima T., Fukuzumi S. J. Am. Chem. Soc. 2008, 130:1556.
111. Koyima T., Morimoto T., Sakamoto T., Miyazaki S., Fukuzumi S. Chem. Eur. J. 2008, 14:8904.
112. To T.T., Heilweil E.J., Duke C.B., Ruddick K.R., Webster C.E., Burkey T.J. J. Phys. Chem. A 2009, 113:2666.
113. To T.T., Barnes C.E., Burkey T.J. Organometallics 2004, 23:2708.
114. Yeston J.S., To T.T., Burkey T.J., Heilweil E.J. J. Phys. Chem. B 2004, 108:4582.
115. Jiao T., Pang Z., Burkey T.J., Johnson R.F., Heimer T.A., Kleiman V.D., Heilweil E.J. J. Am. Chem. Soc. 1999, 121:4618.
116. To T.T., Heilweil E.J., Burkey T.J. J. Phys. Chem. A 2006, 110:10669.
117. To T.T., Heilweil E.J., Duke C.B., Burkey T.J. J. Phys. Chem. A 2007, 111:6933.
118. Patrocinio A.O.T., Iha N.Y.M. Inorg. Chem. 2008, 47:10851.
119. Frin K.P.M., Itokazu K., Iha N.Y.M. Inorg. Chim. Acta 2010, 363:294.
120. Dattelbaum D.M., Itokazu M.K., Iha N.Y.M., Meyer T.J. J. Phys. Chem. 2003, 107:4092.
121. Busby M., Hartl F., Matousek P., Towrie M., Vlček A. Chem. Eur. J. 2008, 14:6912.
122. Busby M., Matousek P., Towrie M., Vlček A. Inorg. Chim. Acta 2007, 360:885.
123. Busby M., Matousek P., Towrie M., Vlček A. J. Phys. Chem. A 2005, 109:3000.
124. Hasegawa Y., Kume S., Nishihara H. Dalton Trans. 2009, 280.
125. Coleman A.C., Draper S.M., Long C., Conor, Pryce M.T. Organometallics 2007, 26:4128.
126. Coleman A.C., Boyle N.M., Long C., Augulis R., Pugzlys A., van Loosdrecht P.H.M., Browne W.R., Feringa B.L., Ronayne K.L., Pryce M.T. Dalton Trans. 2010, 39:229.
127. Some representative examples of thermally induced haptotropic rearrangements:.
128. Jimenez-Halla J.O.C., Robles J., Sol M. Organometallics 2008, 27:5230.
129. Gridnev I.D. Coord. Chem. Rev. 2008, 252:1798.
130. Oprunenko Y., Malyugina S., Vasil'ko A., Lyssenko K., Elschenbroich C., Harms K. J. Organomet. Chem. 2002, 641:208.
131. Dotz K.H., Wenzel B., Jahr H.C. Top. Curr. Chem. 2004, 248:63.
132. Fryzuk M.D., Jafarpour L., Kerton F.M., Love J.B., Rettig S.J. Angew. Chem. Int. Ed. 2000, 39:767.
133. Breheny C.J., Draper S.M., Grevels F.-W., Klozbucher W.E., Long C., Pryce M.T., Russell G. Organometallics 1996, 15:3679.
134. Heenan D.P., Long C., Montiel-Palma V., Perutz R.N., Pryce M.T. Organometallics 2000, 19:3869.
135. Zakrzewski J., Giannotti C. J. Organomet. Chem. 1990, 388:175.
136. Maher K., Long C., Pryce M.T. J. Organomet. Chem. 2006, 691:3298.
137. Brennan P., George M.W., Jina O.S., Long C., McKenna J., Pryce M.T., Sun X.-Z., Vuong K.Q. Organometallics 2008, 27:3671.
138. Niinayashi S., Matsubara K., Haga M.-A., Nagashima H. Organometallics 2004, 23:635.
139. Burger P. Angew. Chem. Int. Ed. 2001, 40:1917.
140. Garcia-Garibay M.A. Angew. Chem. Int. Ed. 2007, 46:8945.
141. Kobatake S., Takami S., Muto H., Ishikawa T., Irie M. Nature 2007, 446:778.
142. Irie M., Kobatake S., Horichi M. Science 2001, 291:1769.
143. Irie M. Chem. Rev. 2000, 100:1685.
144. Tian H., Yang S. Chem. Soc. Rev. 2004, 33:85.
145. For some representative examples see the following:.
146. Aubert V., Guerchais V., Ishow E., Hoang-Thi K., Ledoux I., Nakatani K., Le Bozec H. Angew. Chem. Int. Ed. 2008, 47:577R.
147. Jukes T.F., Adamo V., Hartl F., Belser P., De Cola L., Coord L. Chem. Rev. 2005, 249:1327.
148. Lee J.K.-W., Ko C.-C., Wong K.M.-C., Zhu N., Yam W.-W. Organometallics 2007, 26:12.
149. Ngan T.-W., Ko C.-C., Zhu N., Yam N.W.-W. Inorg. Chem. 2007, 46:1144.
150. Qin B., Yao R., Zhao X., Tian H. Org. Biomol. Chem. 2003, 1:2187.
151. Qin B., Yao R., Tian H. Inorg. Chim. Acta 2004, 357:3382.
152. Zhong Y.-W., Vila N., Henderson J.C., Flores-Torres S., Abruña H.D. Inorg. Chem. 2009, 48:7080.
153. Zhong Y.-W., Vila N., Henderson J.C., Flores-Torres S., Abruña H.D. Inorg. Chem. 2009, 48:991.
154. Zhong Y.-W., Vila N., Henderson J.C., Flores-Torres S., Abruña H.D. Inorg. Chem. 2007, 46:10470.
155. Tanaka Y., Inagaki A., Akita M. Chem. Commun. 2007, 1169.
156. Motoyama K., Koike T., Akita M. Chem. Commun. 2008, 5812.
157. Nakai H., Nonaka T., Miyano Y., Mizuno M., Ozawa Y., Toriumi K., Koga N., Nishioka T., Irie M., Isobe K. J. Am. Chem. Soc. 2008, 130:17836.
158. Nakai H., Mizuno M., Nishioka T., Koga N., Shiomi K., Miyano Y., Irie M., Breedlove B.K., Kinoshita I., Ozawa Y., Toriumi K., Yonezawa T., Isobe K. Angew. Chem. Int. Ed. 2006, 45:6473.
159. Forster R.J., Keyes T.E., Vos J.G. Interfacial Supramolecular Assemblies 2003, Wiley, Chichester.
160. Kudernac T., Katsonis N., Browne W.R., Feringa B.L. J. Mater. Chem. 2009, 19:7168.
161. Browne W.R. Coord. Chem. Rev. 2008, 252:2470.
162. Geraty S.M., Vos J.G. J. Electroanal. Chem. 1984, 176:389.
163. Clear J.M., Kelly J.M., Pepper D.C., Vos J.G. Inorg. Chim. Acta 1979, 33:L139.
164. Haas O., Kriens M., Vos J.G. J. Am. Chem. Soc. 1981, 103:1318.
165. Clear J.M., Kelly J.M., O'Connell C.M., Vos J.G. J. Chem. Res. (M) 1981, 3039.
166. van Delden R.A., ter Wiel M.K.L., Pollard M.M., Vicario J., Koumura N., Feringa B.L. Nature 2005, 437:1337.
167. Browne W.R., Feringa B.L. Annu. Rev. Phys. Chem. 2009, 60:407.
168. Kim K., Jeon W.S., Kang J.-K., Lee J.W., Jon S.Y., Kim T., Kim K. Angew. Chem. Int. Ed. 2003, 42:2293.
169. Chia S.Y., Cao J.G., Stoddart J.F., Zink J.I. Angew. Chem. Int. Ed. 2001, 40:2447.
170. Ferris D.P., Zhao Y.-L., Khashab N.M., Khatib H.A., Stoddart J.F., Zink J.I. J. Am. Chem. Soc. 2009, 131:1686.
171. Zhao Y-L., Hu L.B., Gruner G., Stoddart J.F. J. Am. Chem. Soc. 2008, 130:16996.
172. Frehill F., Vos J.G., Benrezzak S., Rüther M., Blau W.J., Minett A.I., Fonseca A., Nagy J.B., Koos A., Birro L., in het Panhuis M. J. Am. Chem. Soc. 2002, 124:13694.
173. Forster R.J., Keyes T.E. Coord. Chem. Rev. 2009, 253:1833.
174. Gütlich A.P., Goodwin H.A. Top. Curr. Chem. 2004, 233:1.
175. Brooker S., Kitchen J.A. Dalton Trans. 2009, 7331.