Properties of some alkyl substituted phthalocyanines and related macrocycles

Chemical Record

Volumn 2, Issue 4, 2002, Pages 225-236

  Cook, Michael J ^a  

^a UNIVERSITY OF EAST ANGLIA   (United Kingdom)

Author keywords

Langmuir Blodgett; Liquid crystals; Phthalocyanines; Self assembled monolayers; Thin films

Indexed keywords

ARTICLE;

EID: 0037622225     PISSN: 15278999     EISSN: 15280691     Source Type: Journal    
DOI: 10.1002/tcr.10028     Document Type: Article

References (99)

1. (a) Leznoff, C.C.; Lever, A.B.P., Eds.; Phthalocyanines: Properties and Applications, Vols. 1-4; VCH Publishers: New York, 1989, 1993, 1996;
2. (b) Hanack, M.; Heckmann, H.; Polley, R. In Methods in Organic Chemistry (Houben-Weyl), Vol. E9d; Schaumann, E., Ed.; Georg Thieme Verlag: Stuttgart, 1997;
3. (c) McKeown, N.B. Phthalocyanine Materials: Synthesis, Structure and Function; Cambridge University Press: Cambridge, 1998.
4. Moser F.H.; Thomas, A.L. The Phthalocyanines, Vols. 1 and 2, Manufacture and Applications; CRC Press: Boca Raton, FL, 1983.
5. (a) Gregory, P. High-Technology Applications of Organic Colorants; Plenum Press: New York, 1991;
6. (b) Gregory, P. J Porphyrins Phthalocyanines 2000, 4, 432.
7. (a) Ao, R.; Kilmmert, L.; Haarer, D. Adv Mater 1995, 7, 495;
8. (b) Birkett, D. Chem Ind 2000, 178.
9. (a) Wöhrle D.; Meissner, D. Adv Mater 1991, 3, 129;
10. (b) Eichhorn, H. J Porphyrins Phthalocyanines 2000, 4, 88.
11. (a) Wright, J.D. Prog Surf Sci 1989, 31, 1;
12. (b) Snow A.W.; Barger W.R. In Phthalocyanines-Properties and Applications; Leznoff C.C; Lever, A.B.P., Eds.; VCH Publishers: New York, 1989; p 341.
13. (a) Nalwa H.S.; Shirk J.S. In Phthalocyanines-Properties and Applications, Vol 4; Leznoff C.C.; Lever, A.B.P., Eds.; VCH Publishers: New York, 1996; p 79;
14. (b) Shirk, J.S.; Pong, R.G.S.; Flom, S.R.; Heckmann, H.; Hanack, M. J Phys Chem 2000, 104, 1438;
15. (c) de la Torre, G.; Vázquez, P.; Agulló-López, F.; Torres, T. J Mater Chem 1998, 8, 1671.
16. (a) Luk'yanets E.A. J Porphyrins Phthalocyanines 1999, 3, 424;
17. (b) H. Hasrat H.; van Lier, J.E. Chem Rev 1999, 99, 2379.
18. Priola, S.A.; Raines, A.; Caughey, W.S. Science 2000, 287, 1503.
19. Piechocki, C.; Simon, J.; Skoulios, D.; Guillon, D.; Weber, P. J Am Chem Soc 1982, 104, 5245.
20. Simon, J.; Bassoul, P. In Phthalocyanines-Properties and Applications, Vol 2; Leznoff C.C.; Lever, A.B.P., Eds.; VCH Publishers: New York, 1993; p 223.
21. Chandraselchar, S.; Sadashiva, B.K.; Suresh, K.A. Pramana 1977, 9, 471.
22. (a) Ohta, K.; Jaquemin, L.; Sirlin, C.; Bosio, L.; Simon. J New J Chem 1988, 12, 751;
23. (b) Masural, D.; Sirlin, C.; Simon, J. New J Chem 1987, 11, 455.
24. van der Pol, J.F.; Neeleman, E.; Zwikker, J.W.; Nolte, R.J.M.; Drenth, W. Recl Trav Chim Pays-Bas 1988, 107, 615.
25. Cook, M.J.; Daniel, M.F.; Harrison, K.J.; McKeown, N.B.; Thomson, A.J. J Chem Soc Chem Commun 1987, 1086.
26. Cammidge, A.N.; Cook, M.J.; Haslam, S.D.; Richardson, R.M.; Harrison, K.J. Liq Cryst 1993, 14, 1847.
27. Cook, M.J.; Dunn, A.J.; Howe, S.D.; Thomson, A.J.; Harrison, K.J. J Chem Soc Perkin Trans 1 1988, 2453.
28. McKeown, N.B.; Chambrier, I.; Cook, M.J. J Chem Soc Perkin Trans 1 1990, 1169.
29. Cook, M.J.; Chambrier, I.; Cracknell, S.J.; Mayes, D.A.; Russell, D.A. Photochem Photobiol 1995, 62, 542.
30. Chambrier, I.; Cook, M.J.; Helliwell, M.; Powell, A.K. J Chem Soc Chem Commun 1992, 444.
31. Chambrier, I.; Cook, M.J.; Wood, P.T. J Chem Soc Chem Commun 2000, 2133.
32. (a) Cherodian, A.S.; Davies, A.N.; Richardson, R.M.; Cook, M.J.; McKeown, N.B.; Thomson, A.J.; Feijoo, J.; Ungar, G.; Harrison, K.J. Mol Cryst Liq Cryst 1991, 196, 103;
33. (b) Belushkin, A.V.; Cook, M.J.; Frezzato, D.; Haslam, S.D.; Ferrarini, A.; Martin, D.; McMurdo, J.; Nordio, P.L.; Richardson, R.M.; Stafford, A. Mol Phys 1998, 93, 593.
34. Cook, M.J.; Cracknell, S.J.; Harrison, K.J. J Mater Chem 1991, 1, 703.
35. Cook, M.J. J Mater Sci: Mater Electr 1994, 5, 117.
36. Swarts, J.C.; Langner, E.H.G.; Krokeide-Hove, N.; Cook, M.J. J Mater Chem 2001, 11, 434.
37. Jafari-Fini, A.; Cook, M.J. Unpublished data.
38. (a) Critchley, S.M.; Willis, M.R.; Cook, M.J.; McMurdo, J.; Maruyama, Y. J Mater Chem 1992, 2, 157;
39. (b) Critchley, S.M.; Willis, M.R.; Maruyama, Y.; Bandow, S.; Cook, M.J.; McMurdo, J. Mol Cryst Liq Cryst 1993, 229, 47.
40. Cook, M.J.; Mayes, D.A.; Poynter, R.H. J Mater Chem 1995, 5, 2233.
41. Wright, J.D.; Roisin, P.; Rigby, G.P.; Nolte, R.J.M.; Cook, M.J.; Thorpe, S.C. Sens Actuators B 1993, 13-14, 276.
42. Barker, P.S.; Petty, M.C.; Monkman, A.P.; McMurdo, J.; Cook, M.J.; Pride, R. Thin Solid Films 1996, 284-285, 94.
43. Ometto, C.; Fabris, C.; Milanesi, C.; Jori, G.; Cook, M.J.; Russell, D.A. Br J Cancer 1996, 74, 1891.
44. Fabris, C.; Ometto, C.; Milanesi, C.; Jori, G.; Cook, M.J.; Russell, D.A. J Photochem Photobiol B: Biology 1997, 39, 279.
45. Dodsworth, E.S.; Lever, A.B.P.; Seymour, P.; Leznoff, C.C. J Phys Chem 1985, 89, 5698.
46. Kobayashi, N.; Konami, H. In Phthalocyanines-Properties and Applications, Vol. 4; LeznofF, C.C.; Lever, A.B.P., Eds.; VCH Publishers: New York, 1996; p 343.
47. See, e.g., Liu, Y.; Xu, Y.; Zhu, D.; Wada, T.; Sasabe, H.; Liu, L.; Wang, W. Thin Solid Films, 1994, 244, 943;
48. Liu, Y.; Xu, Y.; Zhu, D.; Wada, T.; Sasabe, H.; Zhao, Z.; Xie, X. J Phys Chem 1995, 99, 6957;
49. De la Torre, G.; Vázquez, P.; Aguilló-López, F.; Torres, T. J Mater Chem 1998, 8, 1671.
50. Leznoff, C.C.; Hall, T.W. Tetrahedron Lett 1982, 23, 3023.
51. For a review, see Leznoff, C.C. In Phthalocyanines-Properties and Applications; Leznoff, C.C.; Lever, A.B.P., Eds.; VCH Publishers: New York, 1989; p 5.
52. Kobayashi, N.; Kondo, R.; Nakajima, S-i.; Osa, T. J Am Chem Soc 1990, 112, 9640.
53. Kobayashi, N. J Porphyrins Phthalocyanines 1999, 3, 453.
54. Geyer, M.; Plenzig, F.; Rauschnabel, J.; Hanack, M.; del Rey, B.; Sastre, A.; Torres, T. Synthesis 1996, 1139.
55. Roberts, G.G.; Petty, M.C.; Baker, S.; Fowler, M.T.; Thomas, N.J. Thin Solid Films 1985, 132, 113.
56. Cook, M.J.; Chambrier, I. In The Porphyrin Handbook, Vol. 15; Kadish, K.; Guillard, R.; Smith, K.M., Eds.; Academic Press. Forthcoming.
57. Cook, M.J.; Dunn, A.J.; Daniel, M.F.; Hart, R.C.O.; Richardson, R.M.; Roser, S.J. Thin Solid Films 1988, 159, 395.
58. McKeown, N.B.; Cook, M.J.; Thomson, A.J.; Harrison, K.J.; Daniel, M.F.; Richardson, R.M.; Roser, S.J. Thin Solid Films 1988, 159, 469.
59. Cook, M.J.; Daniel, M.F.; Harrison, K.J.; McKeown, N.B.; Thomson, A.J. J Chem Soc Chem Commun 1987, 15, 1148.
60. McKeown, N.B.; Chambrier, I.; Cook, M.J. J Chem Soc Perkin Trans 1 1990, 1169.
61. Cook, M.J.; McMurdo, J.; Miles, D.A.; Poynter, R.H.; Simmons, J.M.; Haslam, S.D.; Richardson, R.M.; Welford, K. J Mater Chem 1994, 4, 1205.
62. Cook, M.J.; McKeown, N.B.; Simmons, J.M.; Thomson, A.J.; Daniel, M.F.; Harrison, K.J.; Richardson, R.M.; Roser, S.J. J Mater Chem 1991, 1, 121.
63. Dent, N.; Grundy, M.J.; Richardson, R.M.; Roser, S.J.; McKeown, N.B.; Cook, M.J.J Chim Phys 1988, 85, 1004.
64. Vélez, M.; Vieira, S.; Chambrier, I.; Cook, M.J. Langmuir 1998, 14, 4227.
65. Chesters, M.A.; Cook, M.J.; Gallivan, S.L.; Simmons, J.M.; Slater, D.A. Thin Solid Films 1992, 210, 538.
66. Crouch, D.; Thorpe, S.C.; Cook, M.J.; Chambrier, I.; Ray, A.K. Sens Actuators B 1994, 19, 411.
67. Hassan, A.K.; Ray, A.K.; Travis, J.R.; Ghassemlooy, Z.; Cook, M.J.; Abass, A.; Collins, R.A. Sens Actuators B 1998, 49, 235.
68. Ray, A.K.; Nabok, A.; Hassan, A.K.; Cook, M.J. IEEE-Proc IEEE: Circuits Devices Syst 1999, 146, 44.
69. Ulman, A. An Introduction to Ultrathin Films: From Langmuir-Blodgett to Self-Assembly; Academic Press: San Diego, 1991.
70. Simpson, T.R.E.; Russell, D.A.; Chambrier, I.; Cook, M.J.; Horn, A.B.; Thorpe, S.C. Sens Actuators B 1995, 29, 353.
71. Simpson, T.R.E.; Cook, M.J.; Petty, M.C.; Thorpe, S.C.; Russell, D.A. Analyst 1996, 121, 1501.
72. Revell, D.J.; Chambrier, I.; Cook, M.J.; Russell, D.A. J Mater Chem 2000, 10, 31.
73. Simpson, T.R.E.; Revell, D.J.; Cook, M.J.; Russell, D.A. Langmuir 1997, 13, 460.
74. Hone, D.C.; Walker, P.I.; Evans-Gowing, R.; FitzGerald, S.; Beeby, A.; Chambrier, I.; Cook, M.J.; Russell, D.A. Langmuir. 2002, 15, 2985.
75. Cook, M.J.; Hersans, R.; McMurdo, J.; Russell, D.A. J Mater Chem 1996, 6, 149-154.
76. Linstead, R.P.; Noble, E.G.; Wright, J.M. J Chem Soc 1937, 911.
77. (a) Yokote, M.; Shibamiya, F. Kogyo Kagaku Zasshi 1959, 62, 224;
78. (b) Yokote, M.; Shibamiya, F.; Hayakawa, H. Yuki-Gosei Kagaka Kyokai-Shi 1965, 23, 151;
79. (c) Sakamoto, K.; Shibamiya, F.J. Japan Soc Colour Material 1985, 58, 121;
80. (d) Sakamoto, K.; Shibamiya, F.J. Japan Soc Colour Material 1986, 59, 517.
81. Kudrevich, S.V.; Gilbert, S.; van Lier, J.E. J Org Chem 1996, 61, 5706.
82. Cook, M.J.; Jafari-Fini, A. Tetrahedron 2000, 56, 4085.
83. Cook, M.J.; Jafari-Fini, A. J Mater Chem 1997, 7, 2327.
84. Sakamoto, K.; Kato, T.; Cook, M.J. J Porphyrins Phthalocyanines 2001, 5, 742.
85. Bakboord, J.; Cook, M.J.; Hamuryudan, E.J. Porphyrins Phthalocyanines 2000, 4, 510.
86. Bryant, G.C.; Cook, M.J.; Ryan, T.G.; Thorn, A.J. Tetrahedron 1996, 52, 809.
87. Bryant, G.C.; Cook, M.J.; Ryan, T.G.; Thorn, A.J. J Chem Soc Chem Commun 1995, 467.
88. Cook, M.J.; Cooke, G.; Jafari-Fini, A. J Chem Soc Chem Commun 1995, 1995.
89. Cook, M.J.; Cooke, G.; Jafari-Fini, A. J Chem Soc Chem Commun 1996, 1925.
90. (a) Terekhov, D.S.; Nolan, K.J.M.; McArthur, C.R.; Leznoff, C.C. J Org Chem 1996, 61, 3034;
91. (b) Ali, H.; van Lier, J.E. Tetrahedron Lett 1997, 38, 1157;
92. (c) Isago, H.; Terekhov, D.S.; Leznoff, C.C. J Porphyrins Phthalocyanines 1999, 1, 135;
93. (d) Leznoff, C.C.; Li, Z.; Isago, H.; D'Ascanio, A.M.; Terekhov, D.S. J Porphyrins Phthalocyanines 1999, 3, 406.
94. (a) Maya, E.M.; Vázquez, P.; Torres, T. J Chem Soc Chem Commun 1997, 1175;
95. (b) Maya, E.M.; Torres, T. Chem Eur J 1999, 5, 2004;
96. (c) Maya, E.M.; Vázquez, P.; Torres, T.; Gobbi, L.; Diederich, F.; Pyo, S.; Echegoyen, L. J Org Chem 2000, 65, 823.
97. Cook, M.J.; Heeney, M.J. J Chem Soc Chem Commun 2000, 969.
98. Cook, M.J.; Heeney, M.J. Chem Eur J 2000, 6, 3958.
99. García-Frutos, E.M.; Fernández-Lázaro, F.; Maya, E.M.; Vázquez, P.; Torres, T. J Org Chem 2000, 65, 6841.