Five thermodynamic describers for addressing serendipity in the self-assembly of polynuclear complexes in solution

Chemical Communications

Volumn 46, Issue 34, 2010, Pages 6209-6231

  Piguet, Claude ^a  

^a UNIVERSITY OF GENEVA   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

ANALYTIC METHOD; BINDING SITE; CHEMICAL INTERACTION; CHEMICAL STRUCTURE; CHEMISTRY; CROSS LINKING; CYCLIZATION; DIMERIZATION; ENERGY; ENTROPY; GEOMETRY; MICROSCOPY; NUCLEAR MAGNETIC RESONANCE; OSMOLARITY; PHYSICAL CHEMISTRY; REVIEW; RIGIDITY; SOLUTION AND SOLUBILITY; THERMODYNAMICS;

EID: 77955806603     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/c0cc00811g     Document Type: Review

References (133)

1. A. Werner Z. Anorg. Chem. 1893 3 267
2. R. Abegg Z. Anorg. Chem. 1904 39 330
3. G. N. Lewis J. Am. Chem. Soc. 1916 38 762
4. G. Schwarzenbach, Complexometric Titrations, Chapman & Hall, London, 1957
5. F. J. Welcher, The Analytical Uses of EDTA, D. Van Nostrand Company, Inc., New York, 1957
6. J. Ribas Gispert, Coordination Chemistry, Wiley-VCH, Weinheim, 2008
7. L. C. Thompson, in Handbook on the Physics and Chemistry of Rare Earths, ed., K. A. J. Gschneidner, and, L. Eyring,, North Holland Publ. Co. Amsterdam, 1979, ch. 25, vol. 3, p. 209
8. G. Schwarzenbach Helv. Chim. Acta 1952 35 2344
9. A. W. Adamson J. Am. Chem. Soc. 1954 76 1578
10. A. E. Martell Adv. Chem. 1967 62 272
11. D. Munro Chem. Br. 1977 13 100
12. E. L. Simmons J. Chem. Educ. 1979 56 578
13. C.-S. Chung J. Chem. Educ. 1984 61 1062
14. R. J. Motekaitis A. E. Martell R. A. Hancock Coord. Chem. Rev. 1994 133 39
15. G. Ercolani L. Mandolini P. Mencarelli S. Roelens J. Am. Chem. Soc. 1993 115 3901
16. P. I. Kitov D. R. Bundle J. Am. Chem. Soc. 2003 125 16271
17. A. Mulder J. Huskens D. N. Reinhoudt Org. Biomol. Chem. 2004 2 3409
18. D. H. Williams E. Stephens D. P. O'Brien M. Zhou Angew. Chem., Int. Ed. 2004 43 6596
19. J. D. Badjic A. Nelson S. J. Cantrill W. B. Turnbull J. F. Stoddart Acc. Chem. Res. 2005 38 723
20. H.-J. Schneider A. K. Yatsimirsky Chem. Soc. Rev. 2008 37 263
21. T. Rehm C. Schmuck Chem. Commun. 2008 801
22. J.-M. Lehn Angew. Chem., Int. Ed. Engl. 1988 27 89
23. C. J. Pedersen J. Am. Chem. Soc. 1967 89 7017
24. H. K. Frensdorff J. Am. Chem. Soc. 1971 93 600
25. G. W. Gokel, Crown Ethers, Royal Society of Chemistry, Cambridge, 1990
26. B. Dietrich, P. Viout and J.-M. Lehn, Macrocyclic Chemistry: Aspects of Organic and Inorganic Supramolecular Chemistry, VCH, Weinheim, 1993
27. J.-M. Lehn, Supramolecular Chemistry: Concepts and Perspectives, VCH, Weinheim, 1995
28. B. P. Hay R. D. Hancock Coord. Chem. Rev. 2001 212 61
29. J.-M. Lehn A. Rigault J. Siegel J. Harrowfield B. Chevrier D. Moras Proc. Natl. Acad. Sci. U. S. A. 1987 84 2565
30. A. Pfeil J.-M. Lehn J. Chem. Soc., Chem. Commun. 1992 838
31. C. O. Dietrich-Buchecker J. Guilhem C. Pascard J.-P. Sauvage Angew. Chem., Int. Ed. Engl. 1990 29 1154
32. G. A. Breault C. A. Hunter P. C. Mayers Tetrahedron 1999 55 5265
33. J.-P. Collin C. Dietrich-Buchecker C. Hamann D. Jouvenot J.-M. Kern P. Mobian J.-P. Sauvage Compr. Coord. Chem. II 2004 303
34. O. Lukin F. Vögtle Angew. Chem., Int. Ed. 2005 44 1456
35. E. C. Constable Tetrahedron 1992 48 10013
36. E. C. Constable Prog. Inorg. Chem. 1994 42 67
37. D. S. Lawrence T. Jiang M. Levett Chem. Rev. 1995 95 2229
38. D. Philp J. F. Stoddart Angew. Chem., Int. Ed. Engl. 1996 35 1154
39. C. Piguet G. Bernardinelli G. Hopfgartner Chem. Rev. 1997 97 2005
40. C. Piguet J. Inclusion Phenom. Macrocyclic Chem. 1999 34 361
41. D. L. Caulder K. N. Raymond Acc. Chem. Res. 1999 32 975
42. S. Leininger B. Olenyuk P. J. Stang Chem. Rev. 2000 100 853
43. G. F. Swiegers T. J. Malefetse Chem. Rev. 2000 100 3483
44. M. Fujita K. Umemoto M. Yoshizawa N. Fujita T. Kusukawa K. Biradha Chem. Commun. 2001 509
45. G. F. Swiegers T. J. Malefetse J. Inclusion Phenom. Macrocyclic Chem. 2001 40 253
46. M. Albrecht Chem. Rev. 2001 101 3457
47. P. D. Beer E. J. Hayes Coord. Chem. Rev. 2003 240 167
48. M. Fujita M. Tominaga A. Hori B. Therrien Acc. Chem. Res. 2005 38 369
49. V. Maurizot M. Yoshizawa M. Kawano M. Fujita Dalton Trans. 2006 2750
50. E. R. Kay D. A. Leigh F. Zerbetto Angew. Chem., Int. Ed. 2007 46 72
51. T. K. Ronson H. Adams L. P. Harding S. J. A. Pope D. Sykes S. Faulkner M. D. Ward Dalton Trans. 2007 1006
52. R. W. Saalfrank H. Maid A. Scheurer Angew. Chem., Int. Ed. 2008 47 8794
53. B. H. Northrop Y.-R. Zheng K.-W. Chi P. J. Stang Acc. Chem. Res. 2009 42 1554
54. M. D. Ward Chem. Commun. 2009 4487
55. N. Fatin-Rouge S. Blanc E. Leize A. van Dorsselaer P. Baret J.-L. Pierre A. M. Albrecht-Gary Inorg. Chem. 2000 39 5771
56. N. Fatin-Rouge S. Blanc A. Pfeil A. Rigault A.-M. Albrecht-Gary J.-M. Lehn Helv. Chim. Acta 2001 84 1694
57. J. Hamacek S. Blanc M. Elhabiri E. Leize A. van Dorsselaer C. Piguet A. M. Albrecht-Gary J. Am. Chem. Soc. 2003 125 1541
58. M. Elhabiri J. Hamacek J.-C. G. Bünzli A. M. Albrecht-Gary Eur. J. Inorg. Chem. 2004 51
59. M. Elhabiri J. Hamacek N. Humbert J.-C. G. Bünzli A. M. Albrecht-Gary New J. Chem. 2004 28 1096
60. M. Elhabiri A. M. Albrecht-Gary Coord. Chem. Rev. 2008 252 1079
61. G. Ercolani J. Am. Chem. Soc. 2003 125 16097
62. G. Ercolani J. Phys. Chem. B 2003 107 5052
63. J. Hamacek C. Piguet J. Phys. Chem. B 2006 110 7783
64. M. Borkovec J. Hamacek C. Piguet Dalton Trans. 2004 4096
65. J. Hamacek M. Borkovec C. Piguet Chem.-Eur. J. 2005 11 5217
66. J. Hamacek M. Borkovec C. Piguet Chem.-Eur. J. 2005 11 5227
67. M. Borkovec G. J. M. Koper C. Piguet Curr. Opin. Colloid Interface Sci. 2006 11 280
68. C. Piguet M. Borkovec J. Hamacek K. Zeckert Coord. Chem. Rev. 2005 249 705
69. T. M. Fyles C. C. Tong New J. Chem. 2007 31 296
70. C. A. Hunter S. Tomas J. Am. Chem. Soc. 2006 128 8975
71. E. Chekmeneva C. A. Hunter M. J. Packer S. M. Turega J. Am. Chem. Soc. 2008 130 17718
72. C. A. Hunter H. L. Anderson Angew. Chem., Int. Ed. 2009 48 7488
73. A. Camara-Campos D. Musumeci C. A. Hunter S. Turega J. Am. Chem. Soc. 2009 131 18518
74. J. Hamacek M. Borkovec C. Piguet Dalton Trans. 2006 1473
75. E. J. Enemark T. D. P. Stack Inorg. Chem. 1996 35 2719
76. E. J. Enemark T. D. P. Stack Angew. Chem., Int. Ed. 1998 37 932
77. G. Ercolani C. Piguet M. Borkovec J. Hamacek J. Phys. Chem. B 2007 111 12195
78. L. Mandolini Adv. Phys. Org. Chem. 1987 22 1
79. R. E. Powell W. M. Latimer J. Chem. Phys. 1951 19 1139
80. W. Kuhn Kolloid-Z. 1934 68 2
81. H. Jacobson W. H. Stockmayer J. Chem. Phys. 1950 18 1600
82. P. J. Flory U. W. Suter M. Mutter J. Am. Chem. Soc. 1976 98 5733
83. W. P. Jencks Proc. Natl. Acad. Sci. U. S. A. 1981 78 4046
84. M. A. Winnik Chem. Rev. 1981 81 491
85. X. Chi A. J. Guerin R. A. Haycock C. A. Hunter L. D. Sarson J. Chem. Soc., Chem. Commun. 1995 2563
86. G. Ercolani J. Phys. Chem. B 1998 102 5699
87. R. H. Kramer J. W. Karpen Nature 1998 395 710
88. C. Galli L. Mandolini Eur. J. Org. Chem. 2000 3117
89. J. M. Gargano T. Ngo J. Y. Kim D. W. K. Acheson W. J. Lees J. Am. Chem. Soc. 2001 123 12909
90. 21c which could bring some regrettable confusion because the latter term simply corresponds to the advantage (or disadvantage) of the intramolecular connection, but does not involve its variation during the thermodynamic self-assembly process, a change which is required for a non-zero contribution to the cooperativity of the assembly process.
91. L,L 21c.
92. D.-M. Bishop K. J. Laidler J. Chem. Phys. 1965 42 1688
93. S. W. Benson J. Am. Chem. Soc. 1958 80 5151
94. W. F. Bailey A. S. Monahan J. Chem. Educ. 1978 55 489
95. J.-C. G. Bünzli and A. Milicic-Tang, in Handbook on the Physics and Chemistry of Rare Earths, ed., K. A. Gschneidner, and, L. Eyring,, North Holland Publ. Co., Amsterdam, 1995, vol. 21, p. 305
96. A. Escande L. Guénée K.-L. Buchwalder C. Piguet Inorg. Chem. 2009 48 1132
97. N. Dalla Favera L. Guénée G. Bernadinelli C. Piguet Dalton Trans. 2009 7625
98. G. R. Choppin, in Lanthanide Probes in Life, Chemical and Earth Sciences, ed., J.-C. G. Bünzli, and, G. R. Choppin,, Elsevier, Amsterdam, 1989, ch. 1
99. C. Piguet J.-C. G. Bünzli Chem. Soc. Rev. 1999 28 347
100. G. Canard S. Koeller G. Bernardinelli C. Piguet J. Am. Chem. Soc. 2008 130 1025
101. When discussing the theoretical concept, the effective molarity is often referred to as the effective concentration. For the sake of clarity in this feature article, we will use the term effective molarity, EM, for both the theoretical concept and its experimental value (see ref. 8c for more details).
102. N. Dalla Favera J. Hamacek M. Borkovec D. Jeannerat F. Gumy J.-C. G. Bünzli G. Ercolani C. Piguet Chem.-Eur. J. 2008 14 2994
103. G. Ercolani Struct. Bonding 2006 121 167
104. I. Grenthe J. Am. Chem. Soc. 1961 83 360
105. L8,L8.
106. G. Canard C. Piguet Inorg. Chem. 2007 46 3511
107. E. O. Purisima T. Sulea J. Phys. Chem. B 2009 113 8206
108. S. Torelli S. Delahaye A. Hauser G. Bernardinelli C. Piguet Chem.-Eur. J. 2004 10 3503
109. M. Cantuel G. Bernardinelli D. Imbert J.-C. G. Bünzli G. Hopfgartner C. Piguet J. Chem. Soc., Dalton Trans. 2002 1929
110. M. Born Z. Phys. 1920 1 45
111. B. E. Conway, in Modern Aspects of Electrochemistry, ed., B. E. Conway, and, R. E. White,, Kluwer Academic/Plenum Publishers, 2002, pp. 295-323.
112. R. H. Stokes J. Phys. Chem. 1964 86 979
113. T. Abe Bull. Chem. Soc. Jpn. 1991 64 3035
114. A. Kumar J. Phys. Soc. Jpn. 1992 61 4247
115. T. Riis-Johannessen N. Dalla Favera T. K. Todorova S. M. Huber L. Gagliardi C. Piguet Chem.-Eur. J. 2009 15 12702
116. M. Albrecht Chem.-Eur. J. 1997 3 1466
117. M. Albrecht M. Schneider H. Röttele Angew. Chem., Int. Ed. 1999 38 557
118. D. W. Johnson K. N. Raymond Inorg. Chem. 2001 40 5157
119. A. V. Davis K. N. Raymond J. Am. Chem. Soc. 2005 127 7912
120. A. V. Davis D. Fiedler G. Seeber A. Zahl R. van Eldik K. N. Raymond J. Am. Chem. Soc. 2006 128 1324
121. U. Kiehne T. Weilandt A. Lützen Org. Lett. 2007 9 1283
122. N. Dalla Favera U. Kiehne J. Bunzen S. Hyteballe A. Lützen C. Piguet Angew. Chem., Int. Ed. 2010 49 125
123. A. E. Martell and R. M. Smith, Critical Stability Constants, Plenum Press, New York, 1982, vol. 4-5
124. E. Terazzi L. Guénée B. Bocquet J.-F. Lemonnier N. Dalla Favera C. Piguet Chem.-Eur. J. 2009 15 12719
125. J.-F. Lemonnier L. Guénée G. Bernardinelli J.-F. Vigier B. Bocquet C. Piguet Inorg. Chem. 2010 49 1252
126. M. S. Searle D. H. Williams J. Am. Chem. Soc. 1992 114 10690
127. M. S. Searle M. S. Westwell D. H. Williams J. Chem. Soc., Perkin Trans. 2 1995 141
128. D. H. Williams D. P. O'Brien B. Bardsley J. Am. Chem. Soc. 2001 123 737
129. A. A. Levchenko C. K. Yee A. N. Parikh A. Navrotsky Chem. Mater. 2005 17 5428
130. D. M. Ford J. Am. Chem. Soc. 2005 127 16167
131. -1 based on a standard state of 1 m.
132. J.-M. Senegas S. Koeller C. Piguet Chem. Commun. 2005 2235
133. A. M. Najar I. S. Tidmarsh M. D. Ward Inorg. Chem. 2009 48 11871