Functionalised tetrathiafulvalenes: New applications as versatile π- electron systems in materials chemistry

Journal of Materials Chemistry

Volumn 10, Issue 3, 2000, Pages 589-598

  Bryce, Martin R ^a  

^a DURHAM UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

POLYMER; TETRATHIAFULVALENE DERIVATIVE;

ABSORPTION SPECTROSCOPY; ARTICLE; CHEMICAL ANALYSIS; CONDUCTOR; ELECTROCHEMISTRY; ELECTRON; LIQUID CRYSTAL; MATERIALS; OXIDATION REDUCTION REACTION; PROTON NUCLEAR MAGNETIC RESONANCE; SENSOR; STOICHIOMETRY; THERMAL ANALYSIS;

EID: 0034035689     PISSN: 09599428     EISSN: None     Source Type: Journal    
DOI: 10.1039/a908385e     Document Type: Article

References (133)

1. 1 (a) G. Kiesslich, PhD Thesis, University of Würzburg, 1968;
2. (b) F. Wudl, G. M. Smith and E. Hufnagel, J. Chem. Soc., Chem. Commun., 1970, 1453;
3. (c) S. Hünig, G. Kiesslich, D. Scheutzow, R. Zahradnik and P. Carsky, Int. J. Sulfur Chem., Part C, 1971, 6, 109. Dibenzo-TTF was described as early as 1926 (W. R. Hurleyand S. Smiles, J. Chem. Soc., 1926, 1821) and a mixture of dimethyl-TTFs was also known (H. Prinzbach, H. Berger and A. Lüttringhaus, Angew. Chem., 1965, 77, 453; Angew. Chem., Int. Ed. Engl., 1965, 4, 435) but no redox chemistry of the TTF system was reported prior to the thesis of Kiesslich (ref. 1a. For a full report on this work see: S. Hünig, G. Kiesslich, H. Quast and D. Scheutzow, Liebigs Ann. Chem., 1973, 310).
4. (c) S. Hünig, G. Kiesslich, D. Scheutzow, R. Zahradnik and P. Carsky, Int. J. Sulfur Chem., Part C, 1971, 6, 109. Dibenzo-TTF was described as early as 1926 (W. R. Hurley and S. Smiles, J. Chem. Soc., 1926, 1821) and a mixture of dimethyl-TTFs was also known (H. Prinzbach, H. Berger and A. Lüttringhaus, Angew. Chem., 1965, 77, 453; Angew. Chem., Int. Ed. Engl., 1965, 4, 435) but no redox chemistry of the TTF system was reported prior to the thesis of Kiesslich (ref. 1a. For a full report on this work see: S. Hünig, G. Kiesslich, H. Quast and D. Scheutzow, Liebigs Ann. Chem., 1973, 310).
5. (c) S. Hünig, G. Kiesslich, D. Scheutzow, R. Zahradnik and P. Carsky, Int. J. Sulfur Chem., Part C, 1971, 6, 109. Dibenzo-TTF was described as early as 1926 (W. R. Hurleyand S. Smiles, J. Chem. Soc., 1926, 1821) and a mixture of dimethyl-TTFs was also known (H. Prinzbach, H. Berger and A. Lüttringhaus, Angew. Chem., 1965, 77, 453; Angew. Chem., Int. Ed. Engl., 1965, 4, 435) but no redox chemistry of the TTF system was reported prior to the thesis of Kiesslich (ref. 1a. For a full report on this work see: S. Hünig, G. Kiesslich, H. Quast and D. Scheutzow, Liebigs Ann. Chem., 1973, 310).
6. (c) S. Hünig, G. Kiesslich, D. Scheutzow, R. Zahradnik and P. Carsky, Int. J. Sulfur Chem., Part C, 1971, 6, 109. Dibenzo-TTF was described as early as 1926 (W. R. Hurleyand S. Smiles, J. Chem. Soc., 1926, 1821) and a mixture of dimethyl-TTFs was also known (H. Prinzbach, H. Berger and A. Lüttringhaus, Angew. Chem., 1965, 77, 453; Angew. Chem., Int. Ed. Engl., 1965, 4, 435) but no redox chemistry of the TTF system was reported prior to the thesis of Kiesslich (ref. 1a. For a full report on this work see: S. Hünig, G. Kiesslich, H. Quast and D. Scheutzow, Liebigs Ann. Chem., 1973, 310).
7. (c) S. Hünig, G. Kiesslich, D. Scheutzow, R. Zahradnik and P. Carsky, Int. J. Sulfur Chem., Part C, 1971, 6, 109. Dibenzo-TTF was described as early as 1926 (W. R. Hurleyand S. Smiles, J. Chem. Soc., 1926, 1821) and a mixture of dimethyl-TTFs was also known (H. Prinzbach, H. Berger and A. Lüttringhaus, Angew. Chem., 1965, 77, 453; Angew. Chem., Int. Ed. Engl., 1965, 4, 435) but no redox chemistry of the TTF system was reported prior to the thesis of Kiesslich (ref. 1a. For a full report on this work see: S. Hünig, G. Kiesslich, H. Quast and D. Scheutzow, Liebigs Ann. Chem., 1973, 310).
8. 2 For reviews on the development of organic metals see: (a) F. Wudl, Acc. Chem. Res., 1984, 17, 227;
9. (b) J. R. Ferrraro and J. M. Williams, Introduction to Synthetic Electrical Conductors, Academic Press, London, 1987;
10. (c) M. R. Bryce, Chem. Soc. Rev., 1991, 20, 355;
11. (d) J. M. Williams, J. R. Ferraro, R. J. Thorn, K. D. Carlson, U. Geiser, H. H. Wang, A. M. Kini and M.-H. Whangbo, Organic Superconductors (including Fullerenes), Prentice Hall, New Jersey, 1992.
12. 3 F. Wudl, D. Wobschall and E. J. Hufnagel, J. Am. Chem. Soc., 1972, 94, 671.
13. 4 (a) J. Ferraris, D. O. Cowan, V. V. Walatka and J. H. Perlstein, J. Am. Chem. Soc., 1973, 95, 948;
14. (b) L. B. Coleman, M. J. Cohen, D. J. Sandman, F. G. Yamaguchi, A. F. Garito and A. J. Heeger, Solid State Commun., 1973, 12, 1125.
15. 5 For reviews which emphasise the synthesis of TTF derivatives see: (a) M. Narita and C. U. Pittman, Synthesis, 1976, 486;
16. (b) A. Krief, Tetrahedron, 1986, 42, 1209;
17. (c) G. Schukat, A. M. Richter and E. Fanghänel, Sulfur Rep., 1987, 7, 155;
18. (d) J. Garín, Adv. Heterocycl. Chem., 1995, 62, 249;
19. (e) G. Schukat and E. Fanghänel, Sulfur Rep., 1996, 18, 1.
20. 6 For recent reviews see: (a) M. Adam and K. Müllen, Adv. Mater., 1994, 6, 439;
21. (b) M. R. Bryce, J. Mater. Chem., 1995, 5, 181;
22. (c) E. Coronado and C. J. Gómez-García, Chem. Rev., 1998, 98, 273;
23. (d) P. Day and M. Kurmoo, J. Mater. Chem., 1997, 8, 1291;
24. (e) P. Batail, K. Boubekeur, M. Fourmigué and J.-C. P. Gabriel, Chem Mater., 1998, 10, 3005;
25. (f) J. Yamada, H. Nishikawa and K. Kikuchi, J. Mater. Chem., 1999, 9, 617;
26. (g) Y. Yamashita and M. Tomura, J. Mater. Chem., 1998, 8, 1933;
27. (h) G. Saito, in Organic Molecular Solids: Properties and Applications, W. Jones (Ed.), CRC Press, Boca Raton, 1997, Ch. 10, 309-340;
28. (i) Supramolecular Engineering of Synthetic Metallic Materials: Conductors and Magnets, J. Veciana, C. Rovira and D. B. Amabilino (Eds.), NATO ASI Series, Vol. 518, Kluwer, Dordrecht, 1999.
29. 7 (a) A. M. Kini, U. Geiser, H. H. Wang, K. D. Carlson, J. M. Williams, W. K. Kwok, K. G. Vandervoot, J. E. Thompson, D. L. Stupka, D. Jung and M.-H. Whangbo, Inorg. Chem., 1990, 29, 2555;
30. (b) J. M. Williams, A. M. Kini, H. H. Wang, K. D. Carlson, U. Geiser, L. K. Montgomery, G. J. Pyrka, D. M. Watkins, J. K. Kommers, S. J. Boryschuk, A. V. Crouch, W. K. Kwok, J. E. Schirber, D. L. Overmyer, D. Jung and M.-H. Whangbo, Inorg. Chem., 1990, 29, 3274;
31. (c) T. Komatsu, T. Nakamura, N. Matsukawa, H. Yamochi, G. Saito, H. Ito, T. Ishiguro, M. Kusunoki and K. Sakaguchi, Solid State Commun., 1992, 80, 101.
32. 8 A. J. Moore and M. R. Bryce, Synthesis, 1997, 407.
33. 9 (a) J. Garín, J. Orduna, J. Uriel, A. J. Moore, M. R. Bryce, S. Wegener, D. S. Yufit and J. A. K. Howard, Synthesis, 1994, 489;
34. (b) M. R. Bryce, P. J. Skabara, A. J. Moore, A. S. Batsanov, J. A. K. Howard and V. J. Hoy, Tetrahedron, 1997, 53, 17781;
35. For pioneering studies on TTF functionalisation using lithiation methodology see (c) D. C. Green, J. Org. Chem., 1979, 44, 1476.
36. 10 (a) J. Becher, J. Lau, P. Leriche, P. Mørk and N. Svenstrup, J. Chem. Soc., Chem. Commun., 1994, 2715;
37. (b) K. B. Simonsen and J. Becher, Synlett, 1997, 1211.
38. 11 M. R. Bryce, Adv. Mater., 1999, 11, 11.
39. 12 (a) T. Jørgensen, T. K. Hansen and J. Becher, Chem. Soc. Rev., 1994, 23, 41;
40. (b) T. Otsubo, Y. Aso and K. Takimiya, Adv. Mater., 1996, 8, 203;
41. (c) C. Wang, M. R. Bryce, A. S. Batsanov and J. A. K. Howard, Chem. Eur. J., 1997, 3, 1679.
42. 13 (a) G. W. Gokel, Chem. Soc. Rev., 1992, 21, 39;
43. (b) B. Dietrich, P. Viout and J.-M. Lehn, Macrocyclic Chemistry, VCH, Weinheim, 1993.
44. 14 M. Asakawa, S. Iqbal, J. F. Stoddart and N. D. Tinker, Angew. Chem., Int. Ed., 1996, 35, 976.
45. 15 (a) P. D. Beer, Adv. Inorg. Chem., 1992, 39, 79;
46. (b) P. D. Beer, in Molecular Engineering for Advanced Materials (Eds. J. Becher and K. Schaumburg), Kluwer Academic Publishers, Dordrecht, 1995, p. 99;
47. (c) P. D. Beer, Acc. Chem. Res., 1998, 31, 71;
48. (d) P. L. Boulas, M. Gómez-Kaifer and L. Echegoyen, Angew. Chem., Int. Ed., 1998, 37, 216;
49. (e) A. E. Kaifer, Acc. Chem. Res., 1999, 32, 62.
50. 16 T. Otsubo and F. Ogura, Bull. Chem. Soc. Jpn., 1985, 58, 1343.
51. 17 (a) T. K. Hansen, T. Jørgensen, P. C. Stein and J. Becher, J. Org. Chem., 1992, 57, 6403;
52. (b) R. Gasiorowski, T. Jørgensen, J. Møller, T. K. Hansen, M. Pietraszkiewicz and J. Becher, Adv. Mater., 1992, 4, 568.
53. 18 R. Dieing, V. Morisson, A. J. Moore, L. M. Goldenberg, M. R. Bryce, J.-M. Raoul, M. C. Petty, J. Garín, M. Savirón, I. K. Lednev, R. E. Hester and J. N. Moore, J. Chem. Soc., Perkin Trans. 2, 1996, 1587.
54. 19 F. LeDerf, M. Mazari, N. Mercier, E. Levillain, P. Richomme, J. Becher, J. Garín, J. Orduna, A. Gorgues and M. Sallé, Chem. Commun., 1999, 1417.
55. 20 A. Chesney and M. R. Bryce, Tetrahedron: Asymmetry, 1996, 7, 3247.
56. 21 Reviews: (a) H. O. Finklea, in Electroanalytical Chemistry, A. J. Bard and I. Rubenstein (Eds.), Marcel Dekker, New York, 1996, Vol. 19, p. 109;
57. (b) L. M. Goldenberg, M. R. Bryce and M. C. Petty, J. Mater. Chem., 1999, 9, 1957.
58. 22 A. J. Moore, L. M. Goldenberg, M. R. Bryce, M. C. Petty, A. P. Monkman, C. Marenco, J. Yarwood, M. J. Joyce and S. N. Port, Adv. Mater., 1998, 10, 395.
59. 23 The instability of a different TTF SAM upon cycling through the second oxidation was first reported by C. Yip and M. D. Ward, Langmuir, 1994, 10, 549.
60. 24 H. Fujihara, H. Nakai, M. Yoshihara and T. Maeshima, Chem. Commun., 1999, 737.
61. 25 H. Liu and L. Echegoyen, Chem. Commun., 1999, 1493.
62. 26 For a review of LC display devices see: G. W. Gray and S. M. Kelly, J. Mater. Chem., 1999, 9, 2027.
63. 27 For an early report of smectic and nematic behaviour in 4,5′-(4-alkylphenyl) TTFs see: U. T. Muller-Westerhoff, A. Nazzal, R. J. Cox and A.-M. Giroud, J. Chem. Soc., Chem. Commun., 1980, 497.
64. 28 M. J. Cook, G. Cooke and A. Jafari-Fini, Chem. Commun., 1996, 1925.
65. 29 (a) M. A. Blower, M. R. Bryce and W. Devonport, Adv. Mater., 1996, 8, 63;
66. (b) C. Wang, M. R. Bryce, A. S. Batsanov, C. F. Stanley, A. Beeby and J. A. K. Howard, J. Chem. Soc., Perkin Trans. 2, 1997, 1671.
67. 30 R. Andreu, J. Barberá, J. Garín, J. Orduna, J. L. Serrano, T. Sierra, P. Leriche, M. Sallé, A. Riou, M. Jubault and A. Gorgues, J. Mater. Chem., 1998, 8, 881.
68. 31 R. A. Bissell, N. Boden, R. J. Bushby, C. W. G. Fishwick, E. Holland, B. Movaghar and G. Ungar, Chem. Commun., 1998, 113.
69. 32 Review: N. Boden, R. J. Bushby, J. Clemens and B. Movaghar, J. Mater. Chem., 1999, 9, 2081.
70. 33 Reviews:(a) M. N. Paddon-Row, Acc. Chem. Res., 1994, 27, 18;
71. (b) H. Imahori and Y. Sasaka, Adv. Mater., 1997, 9, 537;
72. (c) T. Verbiest, S. Houbrechts, M. Kauranen, K. Clay and A. Persoons, J. Mater. Chem., 1997, 7, 2175;
73. (d) G. J. Ashwell, J. Mater. Chem., 1999, 9, 1991.
74. 34 A. Aviram and M. Ratner, Chem. Phys. Lett., 1974, 29, 277. For a recent discussion of this proposal see: R. M. Metzger, J. Mater. Chem., 1999, 9, 2027.
75. 34 A. Aviram and M. Ratner, Chem. Phys. Lett., 1974, 29, 277. For a recent discussion of this proposal see: R. M. Metzger, J. Mater. Chem., 1999, 9, 2027.
76. 35 C. A. Panetta, J. Baghdadchi and R. M. Metzger, Mol. Cryst. Liq. Cryst., 1984, 107, 103.
77. 36 P. de Miguel, M. R. Bryce, L. M. Goldenberg, A. Beeby, V. Khodorkovsky, L. Shapiro, A. Niemz, A. O. Cuello and V. Rotello, J. Mater. Chem., 1998, 8, 71.
78. 37 S. Scheib, M. P. Cava, J. W. Baldwin and R. M. Metzger, J. Org. Chem., 1998, 63, 1198.
79. 38 For reviews of DCNQI and TCNQ acceptors see: (a) S. Hünig, J. Mater. Chem., 1995, 5, 1469;
80. (b) Martín, J. L. Segura and C. Seoane, J. Mater. Chem., 1997, 7, 1661.
81. 39 E. Tsiperman, T. Regev, J. Y. Becker, J. Bernstein, A. Ellern, V. Khodorkovsky, A. Shames and L. Shapiro, Chem. Commun., 1999, 1125. The statement in this communication that "systems involving TTF-π-TCNQ are known" and the references given are misleading. Such π-linked systems have not been reported.
82. 40 D. Perepichka and M. R. Bryce, unpublished results.
83. 41 Reviews: (a) M. Prato, J. Mater. Chem., 1997, 7, 1097;
84. (b) N. Martín L. Sánchez, B. Illescas and I. Pérez, Chem. Rev., 1998, 98, 2527.
85. 42 (a) M. Prato, M. Maggini, C. Giacometti, G. Scorrano, G. Sandona and G. Farnia, Tetrahedron, 1996, 52, 5221;
86. (b) N. Martín, L. Sánchez, C. Seoane, R. Andreu, J. Garín and J. Orduna, Tetrahedron Lett., 1996, 37, 5979;
87. (c) J. Llacay, J. Veciana, J. Vidal-Gancedo, J. L. Bourdelande, R. González-Moreno and C. Rovira, J. Org. Chem., 1998, 121, 3951;
88. (d) K. B. Simonsen, V. V. Konovalov, T. A. Konovalova, T. Kawai, M. P. Cava, L. D. Kispert, R. M. Metzger and J. Becher, J. Chem. Soc., Perkin Trans. 2, 1999, 657.
89. 43 (a) R. Andreu, A. I. De Lucas, J. Garín, N. Martín, L. Sánchez and C. Seoane, Synth. Met., 1997, 86, 1817;
90. (b) A. I. de Lucas, N. Martín, J. Orduna, L. Sánchez, C. Seoane, R. Andreu, J. Garín, J. Orduna, R. Alcalá and B. Villacampa, Tetrahedron, 1998, 54, 4665.
91. 44 A. Green, PhD Thesis, University of Durham, 1997.
92. 45 H. Meier, R. Petermann and J. Gerold, Chem. Commun., 1999, 977.
93. 46 Reviews: (a) V. Balzani, M. Gómez-López and J. F. Stoddart, Acc. Chem., 1998, 31, 405;
94. (b) X. Marguerettaz, A. Merrins and D. Fitzmaurice, J. Mater. Chem., 1998, 8, 2157;
95. (c) A. Niemz and V. Rotello, Acc. Chem. Res., 1999, 32, 44.
96. 47 L. M. Goldenberg and O. Neilands, J. Electroanal. Chem., 1999, 463, 212.
97. 48 M. B. Nielsen, S. B. Nielsen and J. Becher, Chem. Commun., 1998, 475;
98. M.B. Nielsen, J. G. Hansen and J. Becher, Eur. J. Org. Chem., 1999, 2807.
99. 49 For related studies on the intermolecular host properties of this macrocyclic acceptor towards TTF (to form TTF pseudorotaxanes, rotaxanes and catenanes) see: (a) D. Philp, A. M. Z. Slawin, N. Spencer, J. F. Stoddart and D. J. Williams, J. Chem. Soc., Chem. Commun., 1991, 1584;
100. (b) W. Devonport, M. A. Blower, M. R. Bryce and L. M. Goldenberg, J. Org. Chem., 1997, 62, 885;
101. (c) M. B. Nielsen, Z. -T. Li and J. Becher, J. Mater. Chem., 1997, 7, 1175;
102. (d) M. Asakawa, P. R. Ashton, V. Balzani, A. Credi, G. Mattersteig, O. A. Matthews, M. Montalti, N. Spencer, J. F. Stoddart and M. Venturi, Chem. Eur. J., 1997, 3, 1992. For related studies on a bis(2-oxypropylene-1,3-dithio) TTF derivative see: M. Asakawa, P. R. Ashton, V. Balzani, S. E. Boyd, A. Credi, G. Mattersteig, S. Menzer, M. Montalti, F. M. Raymo, C. Ruffilli, J. F. Stoddart,M. Venturi and D. J. Williams, Eur. J. Org. Chem., 1999, 985.
103. (d) M. Asakawa, P. R. Ashton, V. Balzani, A. Credi, G. Mattersteig, O. A. Matthews, M. Montalti, N. Spencer, J. F. Stoddart and M. Venturi, Chem. Eur. J., 1997, 3, 1992. For related studies on a bis(2-oxypropylene-1,3-dithio) TTF derivative see: M. Asakawa, P. R. Ashton, V. Balzani, S. E. Boyd, A. Credi, G. Mattersteig, S. Menzer, M. Montalti, F. M. Raymo, C. Ruffilli, J. F. Stoddart, M. Venturi and D. J. Williams, Eur. J. Org. Chem., 1999, 985.
104. 50 M. Asakawa, P. R. Ashton, V. Balzani, A. Credi, C. Hamers, G. Mattersteig, M. Montalti, A. N. Shipway, N. Spencer, J. F. Stoddart, M. S. Tolley, M. Venturi, A. J. P. White and D. J. Williams, Angew. Chem., Int. Ed., 1998, 37, 333.
105. 51 Structure 28 illustrates the fact that it is often impossible to separate the 4,4′ (Z) and 4,5′ (E) isomers of a disubstituted TTF. These isomers interconvert readily under any conditions which generate the cation radical: (a) A. Souizi, A. Robert, P. Batail and L. Ouahab, J. Org. Chem., 1987, 52, 1610;
106. (b) K. Boubekeur, C. Lenoir, P. Batail, R. Carlier, A. Tallec, M.-P. Le Paillard, D. Lorcy and A. Robert, Angew. Chem., Int. Ed. Engl., 1994, 33, 1379.
107. 52 P. R. Ashton, V. Balzani, J. Becher, A. Credi, M. C. T. Fyfe, G. Mattersteig, S. Menzer, M. B. Nielsen, F. M. Raymo, J. F. Stoddart, M. Venturi and D. J. Williams, J. Am. Chem. Soc., 1999, 121, 3951.
108. 53 (a) C. U. Pittman Jr., M. Narita and Y. F. Liang, Macromolécules, 1976, 9, 380;
109. (b) W. R. Hertler, J. Org. Chem., 1976, 41, 1412;
110. (c) G. Inzelt, J. Q. Chambers and F. B. Kaufman, J. Electroanal. Chem., 1983, 159, 443.
111. 54 S. Frenzel, S. Arndt, R. M. Gregorious and K. Müllen, J. Mater. Chem., 1995, 5, 1529.
112. 55 M. R. Bryce, A. D. Chissel, J. Gopal, P. Kathirgamanathan and D. Parker, Synth. Met., 1991, 39, 397.
113. 56 P. J. Skabara, K. Müllen, M. R. Bryce, J. A. K. Howard and A. S. Batsanov, J. Mater. Chem., 1998, 8, 1719.
114. 57 (a) A. Charlton, A. E. Underhill, G. Williams, M. Kalaji, P. J. Murphy, K. M. A. Malik and M. B. Hursthouse, J. Org. Chem., 1997, 62, 3098;
115. (b) P. J. Skabara and K. Müllen, Synth. Met., 1997, 84, 345.
116. 58 (a) C. Thobie-Gautier, A. Gorgues, M. Jubault and J. Roncali, Macromolecules, 1993, 6, 4094;
117. (b) L. Huchet, S. Akoudad and J. Roncali, Adv. Mater., 1998, 10, 541;
118. (c) L. Huchet, S. Akoudad, E. Levillain, J. Roncali, A. Emge and P. Bäuerle, J. Phys. Chem., 1998, 102, 7776;
119. (d) Review: J. Roncali, J. Mater. Chem., 1997, 7, 2307.
120. 59 Review: J. Roncali, J. Mater. Chem., 1999, 9, 1875.
121. 60 T. Yamamoto and T. Shimizu, J. Mater. Chem., 1997, 7, 1967.
122. 61 Reviews: (a) G. R. Newkome, C. N. Moorefield and F. Vögtle, Dendritic Molecules: Concepts, Synthesis, Perspectives, VCH, Weinheim, 1996;
123. (b) N. Ardoin and D. Astruc, Bull. Soc. Chim. Fr., 1996, 132, 875;
124. (c) M. Fischer and F. Vögtle, Angew. Chem., Int. Ed., 1999, 38, 885.
125. 62 For a review of redox-active dendrimers see: M. R. Bryce and W. Devonport, in Advances in Dendritic Macromolecules, G. R. Newkome (Ed.), JAI Press, London, 1996, Vol. 3, p. 115.
126. 63 (a) M. R. Bryce, W. Devonport and A. J. Moore, Angew. Chem., Int. Ed. Engl., 1994, 33, 1761;
127. (b) W. Devonport, M. R. Bryce, G. J. Marshallsay, A. J. Moore and L. M. Goldenberg, J. Mater. Chem., 1998, 8, 1361.
128. 64 M. R. Bryce, P. de Miguel and W. Devonport, Chem. Commun., 1998, 2565.
129. 65 C. Wang, M. R. Bryce, A. S. Batsanov, L. M. Goldenberg and J. A. K. Howard, J. Mater. Chem., 1997, 7, 1189.
130. 66 C. A. Christensen, L. M. Goldenberg, M. R. Bryce and J. Becher, Chem, Commun., 1998, 509.
131. 67 Review: V. V. Narayanan and G. R. Newkome, Top. Curr. Chem., 1998, 197, 19.
132. 68 U. Simon, Adv. Mater., 1998, 10, 1487.
133. 69 G. Saito, Lecture presented at the 4th International Symposium on Functional Dyes, Osaka, June 1999.