Application of MCD spectroscopy to porphyrinoids

Coordination Chemistry Reviews

Volumn 251, Issue 3-4, 2007, Pages 429-453

  Mack, John ^a,b   Stillman, Martin J ^b   Kobayashi, Nagao ^a  

^a TOHOKU UNIVERSITY   (Japan)

^b UNIVERSITY OF WESTERN ONTARIO   (Canada)

Author keywords

DFT; INDO; MCD spectroscopy; MO calculations; Phthalocyanine; Porphyrin

Indexed keywords

EID: 33846580125     PISSN: 00108545     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ccr.2006.05.011     Document Type: Review

References (138)

1. http://www.uwo.ca/chem/people/faculty/stillman.htm
2. http://www.chem.tohoku.ac.jp/labo/kinoubunsi/e.html
3. In: Dolphin D. (Ed). The Porphyrins (1978), Academic Press, New York
4. Dolphin D. Ann. NY Acad. Sci. 206 (1973)
5. In: Kadish K.M., Smith K.M., and Guilard R. (Eds). The Porphyrin Handbook (1999), Academic Press, New York
6. In: Leznoff C.C., and Lever A.B.P. (Eds). Phthalocyanine. Principles and Properties vols. 1-4 (1996), VCH Publications, New York
7. Paolesse R. In: Kadish K.M., Smith K.M., and Guilard R. (Eds). The Porphyrin Handbook vol. 2 (2000), Academic Press, London 201 (chapter 11)
8. Erben C., Will S., and Kadish K.M. In: Kadish K.M., Smith K.M., and Guilard R. (Eds). The Porphyrin Handbook vol. 2 (2000), Academic Press, London 232 (chapter 11)
9. Kobayashi N. In: Kadish K.M., Smith K.M., and Guilard R. (Eds). The Porphyrin Handbook vol. 2 (2000), Academic Press, London 301
10. Houssier C., and Sauer K. J. Am. Chem. Soc. 92 (1970) 779
11. In: Deisenhofer J., and Norris J.R. (Eds). The Photosynthetic Reaction Center (1993), Academic Press, San Diego
12. Fukuzumi S. Pure Appl. Chem. 75 (2003) 577
13. Dawson J.H., and Dooley D.M. In: Lever A.B.P., and Gray H.B. (Eds). Iron Porphyrins vol. 4 (1989), VCH, London 1
14. Cheek J., and Dawson J. In: Kadish K.M., Smith K.M., and Guilard R. (Eds). The Porphyrin Handbook vol. 7 (2000), Academic Press, New York 339
15. Kirk M.L., and Peariso K. Curr. Opin. Chem. Biol. 7 (2003) 20
16. Solomon E.I., Pavel E.G., Loeb K.E., and Campochiaro C. Coord. Chem. Rev. 144 (1995) 369
17. Stephens P.J. Adv. Chem. Phys. 35 (1976) 197
18. Piepho S.B., and Schatz P.N. Group Theory in Spectroscopy with Applications to Magnetic Circular Dichroism (1983), Wiley, New York
19. Simpson W.T. J. Chem. Phys. 17 (1949) 1218
20. Platt J.R. J. Chem. Phys. 17 (1949) 484
21. Platt J.R. In: Hollander A. (Ed). Radiation Biology vol. III (1956), McGraw-Hill Book Co., New York (chapter 2)
22. Moffitt W. J. Chem. Phys. 22 (1954) 320
23. Moffitt W. J. Chem. Phys. 22 (1954) 1820
24. Gouterman M. J. Chem. Phys. 30 (1959) 1139
25. Gouterman M. J. Mol. Spectrosc. 6 (1961) 138
26. McHugh A.J., Gouterman M., and Weiss Jr. C. Theor. Chim. Acta 24 (1972) 346
27. Gouterman M. In: Dolphin D. (Ed). The Porphyrins vol. III (1978), Academic Press, New York 1 part A
28. Schaffer A.M., Gouterman M., and Davidson E.R. Theor. Chim. Acta 30 (1973) 9
29. Michl J. J. Am. Chem. Soc. 100 (1978) 6801 (and the other 16 articles within the same issue)
30. Michl J. Pure Appl. Chem. 52 (1980) 1549
31. Lash T.D. In: Kadish K.M., Smith K.M., and Guilard R. (Eds). The Porphyrin Handbook vol. 2 (2000), Academic Press, London 125 (chapter 10)
32. In: Atkins P., and de Paula J. (Eds). Atkins' Physical Chemistry (2004), Oxford University Press, Oxford
33. In: Charney E. (Ed). The Molecular Basis of Optical Activity. Optical Rotatory Dispersion and Circular Dirchroism (1979), John Wiley & Sons, New York
34. Zeeman P. Phil. Mag. 43 (1897) 226
35. Zeeman P. Nobel Lectures, Physics 1901-1921 (1967), Elsevier Publishing Company, Amsterdam
36. Faraday M. Phil. Mag. 28 (1846) 294
37. Faraday M. Phil. Trans. R. Soc. Lond. (1846) 1
38. Canters G.W., and van der Waals J.H. In: Dolphin D. (Ed). The Porphyrins vol. III (1978), Academic Press, New York 531 part A
39. Shashoua V.E. J. Am. Chem. Soc. 87 (1965) 4044
40. Volkenstein M.V., Sharanov J.A., and Shemelin A.K. Nature 209 (1966) 709
41. Shashoua V.E. J. Am. Chem. Soc. 86 (1964) 2109
42. Briat B. Compt. Rend. 259 (1964) 2408
43. Stephens P.J. Inorg. Chem. 4 (1965) 1690
44. Stephens P.J. J. Phys. Chem. 43 (1965) 4444
45. Stephens P.J., Süetaka W., and Schatz P.N. J. Chem. Phys. 44 (1966) 4592
46. Buckingham A.D., and Stephens P.J. Ann. Rev. Phys. Chem. 17 (1966) 399
47. Serber R. Phys. Rev. 41 (1932) 489
48. Henry C.H., Schatterly S.E., and Slichter C.P. Phys. Rev. A 137 (1965) 583
49. Schatz P.N., McCaffery A.J., Süetaka W., Henning G.N., Ritchie A.B., and Stephens P.J. J. Chem. Phys. 45 (1966) 722
50. Briat B., Schooley D.A., Records R., Bunnenberg E., and Djerassi C. J. Am. Chem. Soc. 89 (1967) 6170
51. Schatz P.N., and McCaffery A.J. Q. Rev. Chem. Soc. 23 (1969) 552
52. Shillady D.D., Castevens C.M., Trindle C., Sulik J., and Klonowski P. Biophys. Chem. 105 (2003) 471
53. Dobkowski J., Galievsky V., Starukhin A., Vogel E., and Waluk J. J. Phys. Chem. A 102 (1998) 4996
54. Gorski A., Lament B., Davis J.M., Sessler J.L., and Waluk J. J. Phys. Chem. A 105 (2001) 4992
55. Gorski A., Vogel E., Sessler J.L., and Waluk J. J. Phys. Chem. A 106 (2002) 8139
56. Stephens P.J. J. Chem. Phys. 52 (1970) 3489
57. Stephens P.J. Ann. Rev. Phys. Chem. 25 (1974) 201
58. Williamson B.E., VanCott T.C., Boyle M.E., Misener G.C., Stillman M.J., and Schatz P.N. J. Am. Chem. Soc. 114 (1992) 2412
59. Watson J.D., and Crick F.H.C. Nature 171 (1953) 737
60. Corwin A.H., Chivvis A.B., Poor R.W., Whitten D.G., and Baker E.W. J. Am. Chem. Soc. 90 (1968) 6577
61. Ceulemans A., Oldenhof W., Görller-Walrand C., and Vanquickenborne L.G. J. Am. Chem. Soc. 108 (1986) 1155
62. Barth G., Linder R.E., Bunnenberg E., Djerassi C., Seamans L., and Moscowitz A. J. Chem. Soc. Perkin II (1974) 1706
63. Stillman M.J., and Nyokong T. In: Leznoff C.C., and Lever A.B.P. (Eds). Phthalocyanine. Principles and Properties vol. 1 (1989), VCH Publications, New York 133
64. Stillman M.J. In: Leznoff C.C., and Lever A.B.P. (Eds). Phthalocyanine. Principles and Properties vol. 3 (1993), VCH Publications, New York 227
65. Mack J., and Stillman M.J. In: Kadish K.M., Smith K.M., and Guilard R. (Eds). Handbook of Porphyrins and Related Macrocycles vol. 16 (2003), Academic Press, New York 43
66. Mack J., and Stillman M.J. Coord. Chem. Rev. 219-221 (2001) 993
67. Stillman M.J., and Thomson A.J. J. Chem. Soc. Faraday Trans. II 70 (1974) 805
68. Mack J., and Stillman M.J. J. Am. Chem. Soc. 116 (1994) 1292
69. Mack J., and Stillman M.J. Inorg. Chem. 36 (1997) 413
70. Nyokong T., Gasyna Z., and Stillman M.J. Inorg. Chem. 26 (1987) 1087
71. Ough E.A., and Stillman M.J. Inorg. Chem. 33 (1994) 573
72. Ough E.A., and Stillman M.J. Inorg. Chem. 34 (1995) 4317
73. Nyokong T., Gasyna Z., and Stillman M.J. Inorg. Chem. 26 (1987) 548
74. Ough E.A., Nyokong T., Creber K.A.M., and Stillman M.J. Inorg. Chem. 27 (1988) 2724
75. Ough E.A., Gasyna Z., and Stillman M.J. Inorg. Chem. 30 (1991) 2301
76. Mack J., and Stillman M.J. J. Phys. Chem. 95 (1995) 7935
77. Gasyna Z., Browett W.R., and Stillman M.J. Inorg. Chem. 27 (1988) 4619
78. Nyokong T., Gasyna Z., and Stillman M.J. Inorg. Chim. Acta 112 (1986) 11
79. Browett W.R., and Stillman M.J. Inorg. Chim. Acta 49 (1981) 69
80. Gasyna Z., Browett W.R., Nyokong T., Kitchenham R., and Stillman M.J. Chem. Intell. Lab. Syst. 5 (1989) 233
81. J. Mack, PhD Thesis, University of Western Ontario, 1994.
82. Kobayashi N., Mack J., Ishii K., and Stillman M.J. Inorg. Chem. 41 (2002) 5350
83. Keizer S.P., Mack J., Bench B.A., Gorun S.M., and Stillman M.J. J. Am. Chem. Soc. 125 (2003) 7067
84. Kobayashi N., Furuya F., Yug G.-C., Wakita H., Yokomizo M., and Ishikawa N. Chem. Eur. J. 8 (2002) 1474
85. Kobayashi N., and Fukuda T. J. Am. Chem. Soc. 124 (2002) 8021
86. Kobayashi N., Fukuda T., and Lelievre D. Inorg. Chem. 39 (2000) 3632
87. Makarova E.A., Fukuda T., Luk'yanets E.A., and Kobayashi N. Chem. Eur. J. 11 (2005) 1235
88. Ogata H., Fukuda T., Nakai K., Fujimura Y., Neya S., Stuzhin P.A., and Kobayashi N. Eur. J. Inorg. Chem. 8 (2004) 1621
89. Miwa H., Ishii K., and Kobayashi N. Chem. Eur. J. 10 (2004) 4422
90. Kobayshi N., Miwa H., and Nemykin V.N. J. Am. Chem. Soc. 124 (2002) 8007
91. Mack J., Asano Y., Kobayashi N., and Stillman M.J. J. Am. Chem. Soc. 127 (2005) 17697
92. Keegan J.D., Stolzenberg A.M., Lu Y.C., Linder R.E., Barth G., Moscowitz A., Bunnenberg E., and Djerassi C. J. Am. Chem. Soc. 104 (1982) 4305
93. Keegan J.D., Stolzenberg A.M., Lu Y.C., Linder R.E., Barth G., Moscowitz A., Bunnenberg E., and Djerassi C. J. Am. Chem. Soc. 104 (1982) 4317
94. Djerassi C., Lu Y., Waleh A., Shu A.Y.L., Goldbeck R.A., Kehres L.A., Crandell C.W., Wee A.G.H., Knierzinger A., Gaete-Holmes R., Loew G.H., Clezy P.S., and Bunnenberg E. J. Am. Chem. Soc. 106 (1984) 4241
95. Goldbeck R.A. Acc. Chem. Res. 21 (1988) 95
96. Ishii K., Kobayashi N., Matsuo T., Tanaka M., and Sekiguchi A. J. Am. Chem. Soc. 123 (2001) 5356
97. Perrin M.H. J. Phys. Chem. 59 (1973) 2090
98. In: Parr R.G., and Wang W. (Eds). Density-Functional Theory of Atoms and Molecules (1989), Oxford University Press, Oxford
99. Gross E.K.U., Dobson J.F., and Petersilka M. In: Nalewajski R.F. (Ed). Topics in Current Chemistry vol. 181 (1996), Springer, Berlin 81
100. Van Leeuwen R. Int. J. Mod. Phys. B 15 (2001) 1969
101. Guo L., Ellis D.E., Hoffman B.M., and Ishikawa Y. Inorg. Chem. 35 (1996) 5304
102. Ghosh A. Curr. Opin. Chem. Biol. 7 (2003) 110
103. Gaussian, Inc., Gaussian, Inc. 340 Quinnipiac Street, Building 40, Wallingford, CT 06492.
104. Stephens P.J., Devlin F.J., Cheeseman J.R., and Frisch M.J. J. Phys. Chem. A 105 (2001) 5356
105. Mennucci B., Tomasi J., Cammi R., Cheeseman J.R., Frisch M.J., Devlin F.J., Gabriel S., and Stephens P.J. J. Phys. Chem. A 106 (2002) 6102
106. Grimme S. Chem. Phys. Lett. 339 (2001) 380
107. Grimme S., Furche F., and Ahlrichs R. Chem. Phys. Lett. 361 (2002) 321
108. Autschbach J., Patchkovskii S., Ziegler T., van Gisbergen S.J.A., and Baerends E.J. J. Chem. Phys. 117 (2002) 581
109. Ruud K., and Helgaker T. Chem. Phys. Lett. 352 (2002) 533
110. Furche F., Ahlrichs R., Wachsmann C., Weber E., Sobanski A., Vogtle F., and Grimme S. J. Am. Chem. Soc. 122 (2002) 1717
111. Autschbach J., Ziegler T., van Gisbergen S.J.A., and Baerends E.J. J. Chem. Phys. 116 (2002) 6930
112. Autschbach J., and Ziegler T. J. Chem. Phys. 116 (2002) 891
113. Seth M., Ziegler T., Banerjee A., Autschbach J., van Gisbergen S.J.A., and Baerends E.J. J. Chem. Phys. 120 (2004) 10942
114. Baerends E.J., Ricciardi G., Rosa A., and van Gisbergen S.J.A. Coord. Chem. Rev. 230 (2002) 5
115. Löwdin P.-O. J. Chem. Phys. 18 (1950) 365
116. Lindenberg J. Chem. Phys. Lett. 1 (1967) 39
117. Kintner E.H., and Dawson J.H. Inorg. Chem. 30 (1991) 4892
118. Mack J., Vermeiren C., Heinrichs D.E., and Stillman M.J. Biochem. Biophys. Res. Commun. 320 (2004) 781
119. C. Vermeiren, M. Pluym, J. Mack, D.E. Heinrichs, M.J. Stillman, Biochemistry (2006), in press.
120. Eakanunkul S., Sumithran G.S.L.-R., Ghosh A., Rodgers K.R., Dawson J.H., and Wilks A. Biochemistry 44 (1995) 13179
121. Thomson A.J., and Gadsby P.M.A. J. Chem. Soc. Dalton Trans. (1990) 1921
122. Gadsby P.M.A., and Thomson A.J. J. Am. Chem. Soc. 112 (1990) 5003
123. Cheng J.C., Osborne G.A., Stephens P.J., and Eaton W.A. Nature (London) 241 (1973) 193
124. Rawlings R., Stephens P.J., Nafie L.A., and Kamen M.D. Biochemistry 16 (1977) 1729
125. Kobayashi N., Nozawa T., and Hatano M. Bull. Chem. Soc. Jpn. 54 (1981) 919
126. Yamamoto T., Nozawa T., Kobayashi N., and Hatano M. Bull. Chem. Soc. Jpn. 55 (1982) 3059
127. Schatz P.N., Mowery R.L., and Krausz E.R. Mol. Phys. 35 (1978) 1537
128. Thomson A.J., and Johnson M.K. Biochem. J. 191 (1980) 411
129. Browett W.R., Gasyna Z., and Stillman M.J. J. Am. Chem. Soc. 110 (1987) 3633
130. Foot N., Gadsby P.M.B., Greenwood C., and Thomson A.J. Biochem. J. 261 (1989) 515
131. Oganesyan V.S., and Sharonov Y.A. Spectrochim. Acta A 53 (1997) 433
132. Oganesyan V.S., and Sharonov Y.A. Biochim. Biophys. Acta 1429 (1998) 163
133. Solomon E.I. Chem. Rev. 100 (2000) 235
134. Neidig M.L., Kavana M., Moran G.R., and Solomon E.I. J. Am. Chem. Soc. 126 (2004) 4486
135. Gasyna Z., Browett W.R., and Stillman M.J. Inorg. Chem. 27 (1988) 4619
136. Mack J., Kobayashi N., Leznoff C.C., and Stillman M.J. Inorg. Chem. 36 (1997) 5624
137. Minor P.C., Gouterman M., and Lever A.B.P. Inorg. Chem. 24 (1985) 1894
138. Fujitsu America Inc., CAChe Scientific, 15244 NW Greenbrier Pkwy, Beaverton, OR 97006-5764.