Coordination properties of polyamine-macrocycles containing terpyridine units

Coordination Chemistry Reviews

Volumn 252, Issue 10-11, 2008, Pages 1052-1068

  Bazzicalupi, Carla ^a   Bencini, Andrea ^a   Bianchi, Antonio ^a   Danesi, Andrea ^a   Faggi, Enrico ^a   Giorgi, Claudia ^a   Santarelli, Samuele ^a   Valtancoli, Barbara ^a  

^a UNIVERSITY OF FLORENCE   (Italy)

Author keywords

Macrocycles; Metal complexes; Polyamines; Substrate activation; Terpyridine

Indexed keywords

EID: 41949083174     PISSN: 00108545     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ccr.2007.07.024     Document Type: Review

References (146)

1. Morgan S.G., and Burstall F.H. J. Chem. Soc. (1931) 20
2. McWhinnie W.R., and Miller J.D. Adv. Inorg. Chem. Radiochem. 12 (1969) 135
3. Constable E.C. Adv. Inorg. Chem. Radiochem. 30 (1986) 69
4. Zak B., Baginsky E.S., Epstein E., and Weiner L.M. Clin. Chim. Acta 29 (1970) 77
5. Zak B., Baginsky E.S., Epstein E., and Weiner L.M. Clin. Toxicol. 4 (1971) 621
6. Sauvage J.P., Collin J.P., Chambron J.C., Guillerez S., Coudret C., Balzani V., Barigelletti F., De Cola L., and Flamigni L. Chem. Rev. 94 (1994) 993
7. Balzani V., Venturi M., and Credi A. Molecular Devices and Machines (2003), Wiley-VCH, Weinheim
8. Lindoy L.F., and Atkinson I.M. Self-Assembly in Supramolecular Systems (2000), Royal Society of Chemistry, Cambridge
9. Newkome G.R., Güther R., Moorefield C.N., Cardullo F., Echegoyen L., Pérez-Cordero E., and Luftmann H. Angew. Chem. Int. Ed. Engl. 34 (1995) 2023
10. Newkome G.R., Cardullo F., Constable E.C., Moorefield C.N., and Thompson A.M.W.C. Chem. Commun. (1993) 925
11. Newkome G.R., and He E. J. Mater. Chem. 7 (1997) 1237
12. Schubert U.S., Weidl C.H., Moorefield C.N., Baker G.R., and Newkome G.R. Polym. Prepr. 40 (1999) 940
13. Takada K., Storrier G.D., Morán M., and Abruña H.D. Langmuir 15 (1999) 7333
14. Mutsumi K., Katsutoshi M., Kenji H., and Hirofusa S. Macromol. Rapid Commun. 20 (1999) 98
15. Chow H.-F., Chan I.Y.-K., Fung P.-S., Mong T.K.-K., and Nongrum M.F. Tetrahedron 57 (2001) 1565
16. Diaz D.J., Bernhard S., Storrier G.D., and Abruña H.D. J. Phys. Chem. B 105 (2001) 8746
17. Goldsmith J.I., Takada K., and Abruña H.D. J. Phys. Chem. 106 (2002) 8504
18. Newkome G.R., Yoo K.S., and Moorefield C.N. Chem. Commun. (2002) 2164
19. Takada K., and Abruña H.D. J. Electroanal. Chem. 567 (2004) 249
20. Blasini D.R., Flores-Torres S., Smilgies D.-M., and Abruña H.D. Langmuir 22 (2007) 2082
21. Maskus M., and Abruña H.D. Langmuir 12 (1996) 4455
22. Schubert U.S., Andres P.R., and Hofmeier H. Polym. Mater.: Sci. Eng. 85 (2001) 510
23. Heller M., and Schubert U.S. Macromol. Rapid Commun. 22 (2001) 1358
24. Heller M., and Schubert U.S. Macromol. Rapid Commun. 23 (2002) 411
25. Schubert U.S., and Eschbaumer C. Angew. Chem. Int. Ed. 41 (2002) 2892
26. Gohy J.-F., Lohmeijer B.G.G., and Schubert U.S. Macromolecules 35 (2002) 7427
27. Gohy J.-F., Lohmeijer B.G.G., and Schubert U.S. Macromol. Rapid Commun. 23 (2002) 555
28. Schubert U.S., and Hofmeier H. Macromol. Rapid Commun. 23 (2002) 561
29. Gohy J.-F., Lohmeijer B.G.G., Varshney S.K., and Schubert U.S. Macromolecules 35 (2002) 4560
30. Hanan G.S., Volkmer D., Schubert U.S., Lehn J.-M., Baum G., and Fenske D. Angew. Chem. Int. Ed. Engl. 36 (1997) 1842
31. Semenov A., Spatz J.P., Möller M., Lehn J.-M., Sell B., Schubert D., Weidl C.H., and Schubert U.S. Angew. Chem. Int. Ed. 38 (1999) 1021
32. Pinheiro L.S., and Temperini M.L.A. Surf. Sci. 464 (2000) 176
33. Rice C.R., Ward M.D., Nazeeruddin M.K., and Grätzel M. New J. Chem. 24 (2000) 651
34. Billancia G., Wouters D., Precup A.A., and Schubert U.S. Polym. Mater.: Sci. Eng. 85 (2001) 508
35. Ziener U., Lehn J.-M., Mourran A., and Möller M. Chem. Eur. J. 8 (2002) 951
36. Kurth D.G., Schütte M., and Wen J. Colloid Surf. A: Physicochem. Eng. 198-200 (2002) 633
37. Grätzel M. Inorg. Chem. 44 (2005) 6841
38. Jiménez M.C., Dietrich-Buchecker C.O., and Sauvage J.-P. Angew. Chem. Int. Ed. 39 (2000) 3284
39. Collin J.-P., Dietrich-Buchecker C., Gaviña P., Jimenez-Molero M.C., and Sauvage J.-P. Acc. Chem. Res. 34 (2001) 477
40. Jimenez-Molero M.C., Dietrich-Buchecker C.O., and Sauvage J.-P. Chem. Eur. J. 8 (2002) 1456
41. Livoreil A., Dietrich-Buchecker C.O., and Sauvage J.-P. J. Am. Chem. Soc. 116 (1994) 9399
42. Livoreil A., Sauvage J.-P., Armaroli N., Balzani V., Flamigni L., and Ventura B. J. Am. Chem. Soc. 119 (1997) 12114
43. Baumann F., Livoreil A., and Sauvage J.-P. Chem. Commun. (1997) 35
44. Cárdenas D.J., Livoreil A., and Sauvage J.-P. J. Am. Chem. Soc. 118 (1996) 11980
45. Harriman A., and Ziessel R. Coord. Chem. Rev. 171 (1998) 331
46. Barigelletti F., Flamigni L., Balzani V., Collin J.-P., Sauvage J.-P., Sour A., Constable E.C., and Cargill Thompson A.M.W. J. Chem. Soc., Chem. Commun. (1993) 942
47. Flamigni L., Barigelletti F., Armaroli N., Collin J.-P., Sauvage J.-P., and Williams J.A.G. Chem. Eur. J. 4 (1998) 1744
48. Collin J.-P., Dixon I.M., Sauvage J.-P., Williams J.A.G., Barigelletti F., and Flamigni L. J. Am. Chem. Soc. 121 (1999) 5009
49. Dixon I.M., Collin J.-P., Sauvage J.-P., Barigelletti F., and Flamigni L. Angew. Chem. Int. Ed. 39 (2000) 1292
50. Dixon I.M., Collin J.-P., Sauvage J.-P., and Flamigni L. Inorg. Chem. 40 (2001) 5507
51. Flamigni L. Pure Appl. Chem. 73 (2001) 421
52. Baranoff E., Collin J.-P., Flamigni L., and Sauvage J.-P. Chem. Soc. Rev. 33 (2004) 147
53. Baranoff E., Dixon I.M., Collin J.-P., Sauvage J.-P., Ventura B., and Flamigni L. Inorg. Chem. 43 (2004) 3057
54. Collin J.-P., Harriman A., Heitz V., Odobel F., and Sauvage J.-P. J. Am. Chem. Soc. 116 (1994) 5679
55. Collin J.-P., Gaviña P., Heitz V., and Sauvage J.-P. Eur. J. Inorg. Chem. (1998) 1
56. Constable E.C., and Phillips D. Chem. Commun. (1997) 827
57. Hasenknopf B., and Lehn J.-M. Helv. Chim. Acta 79 (1996) 1643
58. Hasenknopf B., Lehn J.-M., Baum G., and Fenske D. Proc. Natl. Acad. Sci. U.S.A. 93 (1996) 1397
59. Constable E.C., Kulke T., Neuburger M., and Zehnder M. Chem. Commun. (1997) 489
60. Aoyagi M., Biradha K., and Fujita M. J. Am. Chem. Soc. 121 (1999) 7457
61. Sun S.-S., and Lees A.J. Inorg. Chem. 40 (2001) 3154
62. Sun S.-S., Silva A.S., Brinn I.M., and Lees A.J. Inorg. Chem. 39 (2000) 1344
63. Ziesse R. Synthesis (1999) 1839
64. Alcock N.W., Clarke A.J., Errington W., Josceanu A.M., Moore P., Rawle S.C., Sheldon P., Smith S.M., and Turonek M.L. Supramol. Chem. 6 (1996) 281
65. Gleb P.M., Priimov U., Maritim P.K., Butalanyi P.K., and Alcock N.W. J. Chem. Soc., Dalton Trans. (2000) 445
66. Loiseau F., Pietro C.D., Serroni S., Campagna S., Licciardello A., Manfredi A., Pozzi G., and Quici S. Inorg. Chem. 40 (2001) 6901
67. Newkome G.R., Cho T.J., Moorefield C.N., Cush R., Russo P.S., Godínez L.A., Saunders M.J., and Mohapatra P. Chem. Eur. J. 8 (2002) 2946
68. Smith C.B., Constable E.C., Housecroft C.E., and Kariuki B.M. Chem. Commun. (2002) 2068
69. Chow H.S., Constable E.C., Housecroft C.E., and Neuburger M. Dalton Trans. (2003) 4568
70. Constable E.C., Housecroft C.E., and Smith C.B. Inorg. Chem. Commun. 6 (2003) 1011
71. Loren J.C., Yoshizawa M., Haldimann R.F., Linden A., and Siegel J.S. Angew. Chem. Int. Ed. 42 (2003) 5702
72. Andres P.R., and Schubert U.S. Synthesis (2004) 1229
73. Bretonniere Y., Mazzanti M., Pecaut J., and Olmstead M.M. J. Am. Chem. Soc. 124 (2002) 9012
74. Schofield E.R., Collin J.-P., Gruber N., and Sauvage J.-.P. Chem. Commun. (2003) 188
75. Garcia-España E., Gaviña P., Latorre J., Soriano C., and Verdejo B. J. Am. Chem. Soc. 126 (2004) 5082
76. Verdejo B., Aguilar J., Garcia-España E., Gaviña P., Latorre J., Soriano C., Llinares J.M., and Doménech A. Inorg. Chem. 45 (2006) 3803
77. Bazzicalupi C., Bencini A., Bianchi A., Danesi A., Giorgi C., Lodeiro C., Pina F., Santarelli S., and Valtancoli B. Chem. Commun. (2005) 2630
78. Kim D.S.H.L., Ashendel C.L., Zhou Q., Chang C.T., Lee E.S., and Chang C. Bioorg. Med. Chem. Lett. 8 (1998) 2695
79. Xu W.C., Zhou Q., Ashendel C.L., Chang C.T., and Chang C.J. Bioorg. Med. Chem. Lett. 9 (1999) 2279
80. Lowe G., Droz A.S., Vilaivan T., Weaver G.W., Park J.J., Pratt J.M., Tweedale L., and Kelland L.R. J. Med. Chem. 42 (1999) 3167
81. Zhang Y., Murphy C.B., and Jones W.E. Macromolecules 35 (2002) 630
82. Stimmel J.B., Stockstill M.E., and Kull Jr. F.C. Bioconjugate Chem. 6 (1995) 219
83. Stimmel J.B., and Kull Jr. F.C. Nucl. Med. Biol. 25 (1998) 117
84. Costa J., Ruloff R., Burai L., Helm L., and Merbach A.E. J. Am. Chem. Soc. 127 (2005) 5147
85. Ruloff R., Van Koten G., and Merbach A.E. Chem. Commun. (2004) 842
86. Hofmeier H., and Schubert H.S. Chem. Soc. Rev. 33 (2004) 373
87. Schubert U.S., Hofmeier H., and Newkome G.R. Modern Terpyridine Chemistry (2006), Wiley-VCH, Weinheim
88. Grave C., Lentz D., Schäfer A., Sammorì P., Rabe J.P., Franke P., and Schlünter A.D. J. Am. Chem. Soc. 125 (2003) 6907 and references therein cited
89. Drew M.G.B., Hudson M.J., Iveson P.B., Russel M.L., Liljenzin J.-O., Skålberg M., Spjuth L., and Madic C. J. Chem. Soc., Dalton Trans. (1998) 2973
90. Bessel C.A., See R.F., Jameson D.L., Churchill M.R., and Takeuchi K.J. J. Chem. Soc., Dalton Trans. (1992) 3223
91. Bowles K.F., Clark I.P., Cole J.M., Gourlay M., Griffin A.M.E., Mahon M.F., Ooi L., Parker A.W., Raithby P.R., Sparkes H.A., and Towrie M. Cryst. Eng. Commun. 7 (2005) 269
92. Elsbernd H., and Beattie J.K. J. Inorg. Nucl. Chem. 34 (1972) 771
93. Lytle F.E., Petrosky L.M., and Carlson L.R. Anal. Chim. Acta 57 (1971) 239
94. Constable E.C. J. Chem. Soc., Dalton Trans. (1985) 2687
95. Fielding P.E., and Le Fevre R.J.W. J. Chem. Soc. (1951) 1811
96. Nakamoto K. J. Phys. Chem. 64 (1960) 1420
97. Thummel R.P., and Jahng Y. J. Org. Chem. 50 (1985) 2407
98. Siriwardane U., and Hosmane N.S. Acta Crystallogr. C 4 (1988) 1572
99. Chee C.F., Lo K.M., and Ng S.W. Acta Crystallogr. E 59 (2003) m174
100. Prasad L., and Smith F.E. Acta Crystallogr. B 38 (1982) 1815
101. Prasad L., Lee F.L., and Le Page Y. Acta Crystallogr. B 38 (1982) 259
102. Smith R.M., and Martell A.E. NIST Stability Constants Database, version 4.0 (1997), National Institute of Standards and Technology, Washington, DC
103. Hergold-Brundić A., Popović Z., and Matković-Čalogović D. Acta Crystallogr. C 52 (1996) 3154
104. 1H spectra were recorded at 298 K on a Varian Unity 300 MHz instrument. Peak positions are reported relative to DMSO.
105. Sarkar A., and Chakravorti S. J. Lumin. 63 (1995) 143
106. Nakayama Y., Baba Y., Yasuda H., Kawakita K., and Ueyama N. Macromolecules 36 (2003) 7953
107. Kremer S., Henke W., and Reinen D. Inorg. Chem. 21 (1982) 3013
108. Judge J.S., and Baker Jr. W.A. Inorg. Chim. Acta 1 (1967) 68
109. Constable E.C., Lewis J., Liptrot M.C., Raithby P.R., and Schröder M. Polyhedron 2 (1983) 301
110. Constable E.C., Lewis J., Liptrot M.C., and Raithby P.R. J. Chem. Soc., Dalton Trans. (1984) 2177
111. Márquez V.E., Anacona J.R., and Rodriguez Barbarin C. Polyhedron 20 (2001) 1885
112. Márquez V.E., Anacona J.R., and Loroño D. Polyhedron 23 (2004) 1317
113. Chung L.Y., Constable E.C., Khan M.S., Lewis J., Raithby P.R., and Vargas M.D. J. Chem. Soc., Chem. Commun. (1984) 1425
114. Constable E.C., Khan F.K., Lewis J., Liptrot M.C., and Raithby P.R. J. Chem. Soc., Dalton Trans. (1985) 333
115. Márquez V.E., and Anacona J.R. J. Coord. Chem. 49 (2000) 281
116. Márquez V.E., and Anacona J.R. Transition Met. Chem. 25 (2000) 188
117. Márquez V.E., and Anacona J.R. Transition Met. Chem. 29 (2004) 66
118. Márquez V.E., and Anacona J.R. Polyhedron 16 (1997) 2375
119. Constable E.C., Holmes J.M., and McQueen R.C.S. J. Chem. Soc., Dalton Trans. (1987) 5
120. Hughes M.C., Macero D.J., and Rao M. Inorg. Chim. Acta 49 (1981) 241
121. Hughes M.C., Macero D.J., and Rao M. Inorg. Chim. Acta 41 (1980) 221
122. Constable E.C., and Holmes J.M. Polyhedron 7 (1988) 2531
123. Nelson S.M. Pure Appl. Chem. 52 (1980) 2461
124. Guerriero P., Vigato P.A., Fenton D.E., and Hellier P.C. Acta Chem. Scand. 46 (1992) 1025
125. Radecka-Paryzek W., Patroniak V., and Lisowski J. Jerzy. Coord. Chem. Rev. 249 (2005) 2156
126. Borisova N.E., Reshetova M.D., and Ustynyuk Y.A. Chem. Rev. 107 (2007) 46
127. Galup C., Couchet J.M., Picard C., and Tisnès P. Tetrahedron Lett. 42 (2001) 6275
128. Galup C., Couchet J.M., Bedel S., Tisnès P., and Picard C. J. Org. Chem. 70 (2005) 2274
129. Richman J.E., and Atkins T.J. J. Am. Chem. Soc. 96 (1974) 2268
130. Bazzicalupi C., Bencini A., Berni E., Bianchi A., Danesi A., Giorgi C., Valtancoli B., Lodeiro C., Lima J.C., Pina F., and Bernardo M.A. Inorg. Chem. 43 (2004) 5134
131. Bazzicalupi C., Bencini A., Bianchi A., Borsari L., Danesi A., Giorgi C., Mariani P., Pina F., Santarelli S., and Valtancoli B. Dalton Trans. (2006) 5743
132. Walther D., Ruben M., and Rau S. Coord. Chem. Rev. 182 (1999) 67
133. Ito H., and Ito T. Bull. Chem. Soc. Jpn. 58 (1985) 1755
134. Aresta M., Ballivet-Tkatchenko D., Dell'Amico D.B., Bonnet M.C., Boschi D., Calderrazzo F., Faure F., Labella L., and Marchetti F. Chem. Commun. (2000) 1099
135. Xu H., Hampe E.M., and Rudkevich D.M. Chem. Commun. (2003) 2828
136. Belli Dell'Amico D., Calderazzo F., Labella L., Marchetti F., and Pampaloni G. Chem Rev. 103 (2003) 3857
137. Schneider H.-J., and Yatsimirsky A. In: Sigel H., and Sigel A. (Eds). Metal Ion in Biological Systems vol. 40 (2003), Marcel Dekker, New York 369
138. Blasko A., and Bruice T.C. Acc. Chem. Res. 32 (1999) 475
139. Hegg E.L., and Burstyn J.N. Coord. Chem. Rev. 173 (1998) 133
140. Krämer R. Coord. Chem. Rev. 182 (1999) 243
141. Kimura E. Curr. Opt. Chem. Biol. 4 (2000) 207
142. Aoki S., and Kimura E. Rev. Mol. Biotechnol. 90 (2002) 129
143. Weston J. Chem. Rev. 105 6 (2005) 2151
144. Chin J. Curr. Opt. Chem. Biol. 1 4 (1997) 514
145. Scrimin P., and Baltzer L. Curr. Op. Chem. Biol. 9 6 (2005) 620
146. Mancin F., and Tecilla P. New J. Chem. 6 (2007) 800