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Supramolecular chemistry — Scope and perspectives: Molecules — Supermolecules — Molecular devicesJean-Marie LehnInstitut Le BelUniversité Louis PasteurCollège de FranceNobel Lecture, 8 December 1987DOI:
10.1007/BFCite this article as: Lehn, J. Journal of Inclusion Phenomena (1. doi:10.1007/BF
Supramolecular chemistry is the chemistry of the intermolecular bond, covering the structures and functions of the entities formed by association of two or more chemical species. Molecular recognition in the supermolecules formed by receptor-substrate binding rests on the principles of molecular complementarity, as found in spherical and tetrahedral recognition, linear recognition by co-receptors, metallo-receptors, amphilic receptors and anion coordination. Supramolecular catalysis by receptors bearing reactive groups effects bond cleavage reactions as well as synthetic bond formation via co-catalysis. Lipophilic receptor molecules act as selective carriers for various substrates and allow the setting up of coupled transport processes linked to electron and proton gradients or to light. Whereas endo-receptors bind substrates in molecular cavities by convergent interactions, exo-receptors rely on interactions between the surfaces of the recept thus new types of receptors such as the metallonucleates may be designed. In combination with polymolecular assemblies, receptors, carriers and catalysts may lead to molecular and supramolecular devices, defined as structurally organized and functionally integrated chemical systems built on supramolecular architectures. Their recognition, transfer and transformation features are analyzed specifically from the point of view of molecular devices that would operate via photons, electrons or ions, thus defining the fields of molecular photonics, electronics and ionics. Introduction of photosensitive groups yields photoactive receptors for the design of light conversion and charge separation centres. Redox active polyolefinic chains represent molecular wires for electron transfer through membranes. Tubular mesophases formed by stacking of suitable macrocyclic receptors may lead to ion channels. Molecular self-assembling occurs with acyclic ligands that form complexes with a double helical structure. Such developments in molecular and supramolecular design and engineering open perspectives towards the realization of molecular photonic, electronic and ionic devices, that would perform highly selective recognition, reaction and transfer operations for signal and information processing at the molecular level.1.J.-M. Lehn:Struct. Bonding (Berlin)16, 1 (1973).2.J.-M. Lehn:Pure Appl. Chem.
50, 871 (1978).3.J.-M. Lehn: Le?on Inaugurale, Collège de France, Paris 1980.4.R. Pfeiffer:Organische Molekülerverbindungen, Stuttgart, 1927.5.K. L. Wolf, F. Frahm and H. Harms:Z. Phys. Chem. Abt. B
36, 17 (1937); K. L. Wolf, H. Dunken and K. Merked: ibid.Z. Phys. Chem. Abt. B
46, 287 (1940); K. L. Wolf and R. Wolff:Angew. Chem.
61, 191 (1949).6.J.-M. Lehn:Acc. Chem. Res.
11, 49 (1978).7.J.-M. Lehn: in Z. I. Yoshida and N. Ise (Eds.):Biomimetic Chemistry, Kodansha, Tokyo and Elsevier, Amsterdam 1983, p. 163.8.J.-M. Lehn:Science
277, 849 (1985).8.P. G. Potvin and J.-M. Lehn: in R. M. Izatt and J. J. Christensen (Eds.):Synthesis of Macrocycles: The Design of Selective Complexing Agents (Progress in Macrocyclic Chemistry vol. 3), Wiley, New York, 1987, p. 167.10.E. Fischer:Ber. Deutsch. Chem. Gesell.
27, ).11.F. Cramer and W. Freist:Acc. Chem. Res.
20, 79 (1987).12.J. F. Stoddart:Chem. Soc. Rev.
8, 85 (1979);Annual Reports B, Roy. Soc. Chem. (1983) p. 353.13.D. J. Cram and J. M. Cram:Acc. Chem. Res.
11, 8 (1978).14.R. C. Hayward:Chem. Soc. Rev.
12, 285 (1983).15.I. O. Sutherland:Chem. Soc. Rev.
15, 63 (1986).16.G. van Binst (Ed.):Design and Synthesis of Organic Molecules Based on Molecular Recognition, Springer, Berlin 1986.17.(a)J. Rebek, Jr.:Acc. Chem. Res.
17, 258 (1984)17.(b)J. Rebek, Jr.:Science
235, ).18.(a)P. B. Dervan, R. S. Youngquist and J. P. Sluka: in W. Bartmann and K. B. Sharpless (Eds.)Stereochemistry of Organic and Bioorganic Transformations, Verlag Chemie, Heidelberg 1987, p. 22118.(b)W. C. Still:ibid., Verlag Chemie, Heidelberg 1987, p. 235.19.R. M. Izatt, J. J. Christensen (Eds.):Progress in Macrocyclic Chemistry, Wiley, New York, vol. 1 (1979), vol. 2 (1981), vol. 3 (1987).20.F. V?gtle (Ed.):Host Guest Chemistry (Topics Curr. Chem.
98) (1981),101 (1982); F. V?gtle and E. Weber (Eds.),ibid.,Host Guest Chemistry (Topics Curr. Chem.
121 (1984).21.J. L. Atwood, J. E. D. Davies and D. D. MacNicol:Inclusion Compounds, Academic Press, London, vols. 1, 2, 3 (1984).22.G. Wipff, P. K. Kollman and J.-M. Lehn:J. Mol. Struct.
93, 153 (1983); G. Ranghino, S. Romano, J.-M. Lehn and G. Wipff:J. Am. Chem. Soc.
107, ); G. Wipff and P. Kollman:Nouv. J. Chim.
9, 457 (1985); ‘Structure and Dynamics of Macromolecules’, S. Lifson, M. Levitt (Eds.)Isr. J. Chem.
27 (1986) No. 2.23.An idea about the respective role of collection and orientation may be gained from examining the energies calculated for a series of Li(NH3)+n complexes and of the corresponding (NH3)n units in the indentical geometry. In the presence of Li+ the formation energies of the complexes are obtained at the optimized Li+ ... NH3 distances. When Li+ is removed and the NH3 molecules are kept at the same position the energies calculated are for the formation of the coordination shell alone. These energies represent the repulsion between the NH3 they are a measure of the intersite repulsive energy for bringing together two, three or four amine binding sites into a polydentate ligand of the same coordination geometry.Results, (NH3)n, geometry (repulsive energy, kcal/mole): (NH3)2, linear (-2.4), bent (-3.8); (NH3)3, trigonal (-9.1), pyramidal (-10.8); (NH3)4, tetrahedral (-20.8). Thus, the total collection energies are appreciably larger than the organization energies represented by the changes from one geometry to another, linear to bent (1.4 kcal/mole) or trigonal to pyramidal (1.7 kcal/mole).Ab initio computations performed with a set of Gaussian type basis functions, contracted into a double s J.-M. Lehn, R. Ventavoli, see also: R. Ventavoli, 3è Cycle Thesis, Université Louis Pasteur, Strasbourg, 1972.24.(a)Yu. A. Ovchinnikov, V. T. Ivanov and A. M. Skrob:Membrane Active Complexones, Elsevier, New York (1974)24.(b)B. C. Pressman:Ann. Rev. Biochem.
45, 501 (1976)24.(c)H. Brockmann and H. Gerren:Annalen
603, 217 (1957)24.(d)M. M. Shemyakin, N. A. Aldanova, E. I. Vinogradova and M. Yu. Feigina,Tetrahedron Lett. 24.(e)C. Moore and B. C. Pressman:Biochem. Biophys. Res. Commun.
15, 562 (1964)24.(f)B. C. Pressman:Proc. Natl. Acad. Sci. USA
53, )24.(g)J. Beck, H. Gerlach, V. Prelog and W. Voser:Helv. Chim. Acta
74, 620 (1962)24.(h)Z. Stefanac and W. Simon:Chimia
20, 436 (1966) andMicrochem. J.
12, 125 (1967)24.(i)K. T. Kilbourn, J. D. Dunitz, L. A. R. Pioda and W. Simon:J. Mol. Biol.
30, 559 (1967)24.(j)P. Mueller and D. O. Rudin:Biochem. Biophys. Res. Commun.
26, 398 (1967)24.(k)T. E. Andreoli, M. Tieffenberg and D. C. Tosteson:J. Gen. Biol.
50, )24.(l)M. M. Shemyakin, Yu. A. Ovchinnikov, V. T. Ivanov, V. K. Antonov, A. M. Skrob, I. I. Mikhaleva, A. V. Evstratov and G. G. Malenkov:ibid.
29, 834 (1967)24.(m)B. C. Pressman, E. J. Harris, W. S. Jagger and J. H. Johnson:Proc. Natl. Acad. Sci. USA
58, ).25.(a)C. J. Pedersen:J. Am. Chem. Soc.
89, )25.(b)C. J. Pedersen and H. K. Frensdorff:Agnew. Chem. Int. Ed. Engl.
11, 16 (1972).26.D. J. Cram:Angew. Chem. Int. Ed. Engl.
25, ).27.D. Parker:Adv. Inorg. Chem. Radiochem.
27, 1 (1983); B. Dietrich:J. Chem. Ed.
62, 954 (1985). For the sepulchrate type of encapsulated metal ions, see A. M. Sargeson:Pure Appl. Chem.
56, ).28.(a)J.-M. Lehn and J.-P. Sauvage:J. Am. Chem. Soc.
97, )28.(b)B. Dietrich, J.-M. Lehn and J.-P. Sauvage:J. Chem. Soc., Chem. Commun. 1973, 15.29.(a)B. Dietrich, J.-M. Lehn and J.-P. Sauvage:Tetrahedron Lett.
and 288929.(b)B. Dietrich, J.-M. Lehn, J.-P. Sauvage and J. Blanzat, Tetrahedron29, ); B. Dietrich, J.-M. Lehn and J.-P. Sauvage:ibid. Tetrahedron29, )29.(c)B. Metz, D. Moras and R. Weiss:J. Chem. Soc., Chem. Commun. ; F. Mathieu, B. Metz, D. Moras and R. Weiss:J. Am. Chem. Soc.
100, ) and references therein.30.E. Graf and J.-M. Lehn:J. Am. Chem. Soc.
97, );Helv. Chim. Acta
64, ).31.B. Dietrich and J.-M. Lehn: unpublished results.32.E. Graf and J.-M. Lehn:J. Am. Chem. Soc.
98, ).33.F. Schmidtchen and G. Muller:J. Chem. Soc., Chem. Commun. .34.J. L. Dye:Angew. Chem. Int. Ed. Engl.
18, 587 (1979); J. L. Dye and M. G. DeBacker:Ann. Rev. Phys. Chem.
38, 271 (1987).35.J.-M. Lehn:Pure Appl. Chem.
52, ).36.A. I. Popov and J.-M. Lehn: in G. A. Melson (Ed.):Coordination Chemistry of Macrocyclic Compounds Plenum Press, New York, 1979.37.I. M. Kolthoff:Anal. Chem.
51, 1R (1979).38.F. Montanari, D. Landini and F. Rolla:Topics Curr. Chem.
101, 203 (1982); E. Blasius and K.-P. Janzen:ibid. Topics Curr. Chem.
98, 163 (1981).39.E. Graf, J.-M. Lehn and J. LeMoigne:J. Am. Chem. Soc.
104, ).40.E. Graf. J.-P. Kintzinger and J.-M. Lehn: unpublished results.41.B. Dietrich, J.-P. Kintzinger, J.-M. Lehn, B. Metz and A. Zahidi:J. Phys. Chem. in press.42.(a)D. J. Cram and K. N. Trueblood:Topics Curr. Chem.
98, 43 (1981)42.(b)F. De Jong and D. N. Reinhoudt: in V. Gold and D. Bethell (Eds.):Adv. Phys. Org. Chem.
17, 219 (1980), Academic Press, New York.43.J.-M. Lehn and P. Vierling:Tetrahedron Lett. .44.J.-P. Behr, J.-M. Lehn and P. Vierling:J. Chem. Soc., Chem. Commun. ;Helv. Chim. Acta
65, ).45.J.-P. Behr and J.-M. Lehn:Helv. Chim. Acta
63, ).46.H. M. Colquhoun, J. F. Stoddart and D. J. Williams:Angew. Chem. Int. Ed. Engl.
25, 487 (1986).47.Stability constants of about 800 and 105 L mol-1 have been obtained for binding of Ru(NH3)+63 to12b and to the hexacarboxylate in14, respectively (aqueous solution, pH=7.3); J.-M. Lehn and P. Vierling, unpublished results.48.J. C. Metcalfe, J. F. Stoddart and G. Jones:J. Am. Chem. Soc.
99, ); J. Krane and O. Aune:Acta Chem. Scand.
B34, 397 (1980).49.(a)J.-M. Lehn, P. Vierling and R. C. Hayward:J. Chem. Soc., Chem. Commun. 49.(b)see also: K. Madan and D. J. Cram:ibid. J. Chem. Soc., Chem. Commun. ; J. W. H. M. Uiterwijk, S. Harkema, J. Geevers and D. N. Reinhoudt:ibid J. Chem. Soc., Chem. Commun. .50.(a)F. V?gtle, H. Sieger and W. M. Muller:Topics Curr. Chem.
98, 107 (1981)50.(b)K. Saigo:Kagaku to Kygyo
35, 90 (1982)50.(c)J.-L. Pierre and P. Baret:Bull. Soc. Chim. Fr.
II 50.(d)E. Kimura:Topics Curr. Chem.
128, 113 (1985)50.(e)F. P. Schmidtchen:ibid.
132, 101 (1986).51.(a)J.-M. Lehn, E. Sonveaux and A. K. Willard:J. Am. Chem. Soc.
100, )51.(b)B. Dietrich, J. Guilhem, J.-M. Lehn, C. Pascard and E. Sonveaux:Helv. Chim. Acta
67, 91 (1984)51.(c)for other macrobicyclic receptors see also M. W. Hosseini, Thèse de Doctorat-ès-Sciences, Université Louis Pasteur, Strasbourg 1983.52.C. H. Park and H. Simmons:J. Am. Chem. Soc.
90, ).53.(a)B. Dietrich, M. W. Hosseini, J.-M. Lehn and R. B. Sessions:J. Am. Chem. Soc.
103, )53.(b)B. Dietrich, M. W. Hosseini, J.-M. Lehn and R. B. Sessions:Helv. Chim. Acta
68, 289 (1985).54.J. Cullinane, R. I. Gelb, T. N. Margulis and L. J. Zompa:J. Am. Chem. Soc.
104, ); E. Suet and H. Handel:Tetrahedron Lett. .55.M. W. Hosseini, J.-M. Lehn and M. P. Mertes:Helv. Chim. Acta
66, ).56.E. Kimura, M. Kodama and T. Yatsunami:J. Am. Chem. Soc.
104, ); J. F. Marecek and C. J. Burrows:Tetrahedron Lett. .57.M. W. Hosseini and J.-M. Lehn:Helv. Chim. Acta
70, ); see also H. R. Wilson and R. J. P. Williams:J. Chem. Soc., Faraday Trans. I
83, ).58.B. Dietrich, D. L. Fyles, T. M. Fyles and J.-M. Lehn:Helv. Chim. Acta
62, ).59.B. Dietrich, T. M. Fyles, J.-M. Lehn, L. G. Pease and D. L. Fyles:J. Chem. Soc., Chem. Commun. .60.M. J. Mann, N. Pant and A. D. Hamilton:J. Chem. Soc., Chem. Commun. .61.F. Peter, M. Gross, M. W. Hosseini and J.-M. Lehn:J. Electroanal. Chem.
144, 279 (1983).62.E. Garcia-Espana, M. Micheloni, P. Paoletti and A. Bianchi:Inorg. Chim. Acta
102, L9 (1985); A. Bianchi, E. Garcia-Espana, S. Mangani, M. Micheloni, P. Orioli and P. Paoletti:J. Chem. Soc., Chem. Commun. .63.M. F. Manfrin, L. Moggi, V. Castelvetro, V. Balzani, N. W. Hosseini and J.-M. Lehn:J. Am. Chem. Soc.
107, ).64.J.-M. Lehn:Pure Appl. Chem.
52, ).65.J.-M. Lehn, J. Simon and J. Wagner:Angew. Chem. Int. Ed. Engl.
12, 578, 579 (1973).66.R. J. Motekaitis, A. E. Martell, B. Dietrich and J.-M. Lehn:Inorg. Chem.
23, ); R. J. Motekaitis, A. E. Martell and I. Murase:ibid. Inorg. Chem.
25, 938 (1986); A. Evers, R. D. Hancock and I. Murase:ibid. Inorg. Chem.
25, ); D. E. Whitmoyer, D. P. Rillema and G. Gerraudi:J. Chem. Soc., Chem. Commun. .67.J.-P. Kintzinger, J.-M. Lehn, E. Kauffmann, J. L. Dye and A. I. Popov:J. Am. Chem. Soc.
105, ).68.D. Heyer and J.-M. Lehn:Tetrahedron Lett. .69.T. Fujita and J.-M. Lehn: unpublished work.70.T. P. Lybrand, J. A. McCammon and G. Wipff:Proc. Natl. Acad. Sci. USA
83, 833 (1986).71.J.-M. Lehn: in K. J. Laidler (Ed.):IUPAC Frontiers of Chemistry, Pergamon Press, Oxford 1982, p. 265.72.J. Jazwinski, J.-M. Lehn, D. Lilienbaum, R. Ziessel, J. Guilhem and C. Pascard:J. Chem. Soc., Chem. Commun. .73.A. Carroy and J.-M. Lehn:J. Chem. Soc., Chem. Commun. .74.J. Comarmond, B. Dietrich, J.-M. Lehn and R. Louis:J. Chem. Soc., Chem. Commun. 1985, 74.75.Y. Okuno, K. Uoto, O. Yonemitsu and T. Tomohiro:J. Chem. Soc. Chem. Commun. ; J. R. Holmes and J.-M. Lehn: work in progress.76.F. Kotzyba-Hibert, J.-M. Lehn and P. Vierling:Tetrahedron Lett. .77.F. Kotzyba-Hibert, J.-M. Lehn and K. Saigo:J. Am. Chem. Soc.
103, ).78.C. Pascard, C. Riche, M. Cesario, F. Kotzyba-Hibert and J.-M. Lehn:J. Chem. Soc., Chem. Commun. .79.J.-P. Kintzinger, F. Kotzyba-Hibert, J.-M. Lehn, A. Pagelot and K. Saigo:J. Chem. Soc., Chem. Commun. .80.M. W. Hosseini and J.-M. Lehn:J. Am. Chem. Soc.
104, );Helv. Chim. Acta
69, 587 (1986).81.(a)F. P. Schmidtchen:J. Am. Chem. Soc.
108, );81.(b)J. Rebek, Jr. D. Nemeth, P. Ballester and F.-T. Lin:ibid.
109, ).82.J.-M. Lehn, J. Simon and A. Moradpour:Helv. Chim. Acta
61, ).83.(a)F. P. Schmidtchen:J. Org. Chem.
51, );83.(b)J. Simon: Thèse de Doctorat d'Etat, Université Louis Pasteur, Strasbourg 1976; see also structure28 in ref. [14] p. 30583.(c)J. Rebek, Jr., B. Askew, O. Nemeth and K. Parris:J. Am. Chem. Soc.
109, ).84.J.-P. Behr and J.-M. Lehn:J. Am. Chem. Soc.
98, ).85.F. Cramer:Einschlussverbindungen, Springer Verlag, Berlin 1954; M. L. Bender and M. Komiyama:Cyclodextrin Chemistry, Springer Verlag, Berlin 1978.86.(a)J. Franke and F. V?gtle:Topics Curr. Chem.
132, 137 (1986);86.(b)F. V?gtle, W. M. Müller and W. H. Watson:ibid
125, 131 (1984);86.(c)for calixarenes, see C. D. Gutsche:ibid
123, 1 (1984);Acc. Chem. Res.
16. 161 (1983);86.(d)for cavitands, see, D. J. Cram:Science
219, ).87.J. Canceill, A. Collet, J. Gabard, F. Kotzyba-Hibert and J.-M. Lehn:Helv. Chim. Acta
65, ).88.M. Dhaenens, L. Lacombe, J.-M. Lehn and J.-P. Vigneron:J. Chem. Soc., Chem. Commun. .89.H.-J. Schneider, D. Guttes, and U. Schneider:Angew. Chem. Int. Ed. Engl.
25, 647 (1986).90.B. L. Atwood, F. H. Kohnke, J. F. Stoddart and D. J. Williams:Angew. Chem. Int. Ed. Engl.
24, 581 (1985).91.For dissymmetric cylindrical macrotricyclic co-receptors that bind ammonium ions, see A. D. Hamilton and P. Kazanjian:Tetrahedron Lett. ; K. Saigo, R.-J. Lin, M. Kubo, A. Youda and M. Hasegawa:Chem. Lett. .92.For macrocyclic cyclophane type receptors see also K. Odashima, T. Soga and K. Koga:Tetrahedron Lett. ; F. Diederich and K. Dick:ibid.Tetrahedron Lett.
106, ) and references therein.93.A. J. Blacker, J. Jazwinski and J.-M. Lehn:Helv. Chim. Acta
70, 1 (1987).94.I. Bidd, B. Dilworth and J.-M. Lehn: unpublished work.95.J. Jazwinski, A. J. Blacker, J.-M. Lehn, M. Cesario, J. Guilhem and C. Pascard:Tetrahedron Lett. 1987, in press.96.J.-M. Lehn, F. Schmidt and J.-P. Vigneron: work in progress.97.A. J. Blacker, M. W. Hosseini and J.-M. Lehn: unpublished work.98.(a)J.-P. Behr and J.-M. Lehn:98(b).J.-M. Lehn and I. Stibor: work in progress98(c).for recent examples see J. Rebek, Jr., B. Askew, P. Ballester, C. Buhr, S. Jones, D. Nemeth and K., Williams:J. Am. Chem. Soc.
109, ); A. D. Hamilton and D. Van Engen:ibid.J. Am. Chem. Soc.
109, ).99.J. Canceill, M. Cesario, A. Collet, C. Riche and C. Pascard:J. Chem. Soc., Chem. Commun. ; J. Canceill, L. Lacombe and A. Collet:C.R. Acad. Sc. Paris
304, II, 815 (1987).100.A. D. Hamilton, J.-M. Lehn and J. L. Sessler:J. Chem. Soc., Chem. Commun. ;J. Am. Chem. Soc.
108, ).101.For other metalloreceptor type species see for instance references in [15]; N. M. Richards, I. O. Sutherland, P. Camilleri and J. A. Pape:Tetrahedron Lett. ; M. C. Gonzalez and A. C. Weedon:Can. J. Chem.
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104, ); G. B. Maiya and V. Krishnan:Inorg. Chem.
24, ).102.(a)R. Breslow:Science
218, 532 (1982) and in ref. [21] vol. 3, p. 473;102.(b)R. M. Kellogg:Topics Curr. Chem.
101, 111 (1982);102.(c)I. Tabushi and K. Yamamura:ibid.
113, 145 (1983);102.(d)Y. Murakami:ibid.
115, 107 (1983);102.(e)C. Sirlin:Bull. Soc. Chim. France
II, 5 (1984);102.(f)R. M. Kellogg:Angew. Chem. Int. Ed. Engl.
23, 782 (1984);102.(g)V. T. D'Souza and M. Bender:Acc. Chem. Res.
20, 146 (1987).103.J.-M. Lehn:Pure Appl. Chem.
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11, 693 (1987).106.S. Sasaki and K. Koga:Heterocycles
12, ).107.J.-P. Behr and J.-M. Lehn:J. Chem. Soc., Chem. Commun. .108.J.-M. Lehn and T. Nishiya:Chem. Lett. .109.M. W. Hosseini, J.-M. Lehn and M. P. Mertes:Helv. Chim. Acta
66, ); M. W. Hosseini, J.-M. Lehn, L. Maggiora, K. B. Mertes and M. P. Mertes:J. Am. Chem. Soc.
109, 537 (1987).110.G. M. Blackburn, G. R. J. Thatcher, M. W. Hosseini and J.-M. Lehn:Tetrahedron Lett. .111.M. W. Hosseini and J.-M. Lehn:J. Chem. Soc., Chem. Commun. ;J. Am. Chem. Soc.
109, ).112.P. G. Yohannes, M. P. Mertes and K. B. Mertes:J. Am. Chem. Soc.
107, ).113.S. Sasaki, M. Shionoya and K. Koga,J. Am. Chem. Soc.
107, ).114.H.-D. Lutter and F. Diederich:Angew. Chem. Int. Ed. Engl.
25, ).115.F. M. Menger and M. Ladika:J. Am. Chem. Soc.
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226, 505 (1984).117.See, for instance, J. A. Gerlt:Chem. Rev.
87, ); A. J. Russell and A. R. Fersht:Nature
328, 496 (1987).118.A. Tramontano, K. D. Janda and R. A. Lerner:Science
234, ); S. J. Pollack, J. W. Jacobs and P. G. Schultz:ibid.Science
234, ); R. A. Lerner and A. Tramontano:TIBS
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16, 113 (1973); W. E. Morf, D. Amman, R. Bissig, E. Prestsch and W. Simon, in ref. [19], vol. 1, p. 1.122.J.-P. Behr and J.-M. Lehn:J. Am. Chem. Soc.
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45, 501 (1976).124.J. D. Lamb and J. J. Christensen: in ref. [21] vol 3, p. 571.125.M. Kirch and J.-M. Lehn:Angew. Chem. Int. Ed. Engl.
14, 555 (1975); M. Kirsch: Thèse de Doctorat-ès-Sciences, Université Louis Pasteur, Strasbourg, 1980.126.J.-P. Behr, M. Kirch and J.-M. Lehn:J. Am. Chem. Soc.
107, 241 (1985).127.T. M. Fyles:Can. J. Chem.
65, 884 (1987).128.M. Castaing, F. Morel and J.-M. Lehn:J. Membrane Biol.
89, 251 (1986); M. Castaing and J.-M. Lehn:ibid. J. Membrane Biol.
97, 79 (1987).129.E. Bacon, L. Jung and J.-M. Lehn:J. Chem. Res. (S) .130.H. Tsukube:Angew. Chem. Int. Ed. Engl.
21, 304 (1982).131.Anion transport with anion cryptands has been observed recently: T. M. Fyles and J.-M. Lehn, unpublished results.132.F. Diederich and K. Dick:J. Am. Chem. Soc.,106, 8024, (1984); A. Harada and S. Takahashi:J. Chem. Soc., Chem. Commun. .133.J. J. Grimldi and J.-M. Lehn:J. Am. Chem. Soc.
101, ).134.S. S. Anderson, I. G. Lyle and R. Paterson:Nature
259, 147 (1976).135.J. J. Grimaldi, S. Boileau and J.-M. Lehn.Nature
265, 229 (1977).136.J. K. Hurst and D. H. P. Thompson: J. Membrane Sci.28 (1986) an I. Tabushi and S.-i. Kugimiya:Tetrahedron Lett. .137.M. Okahara and Y. Nakatsuji:Topics Curr. Chem.
128, 37 (1985).138.A. Hriciga and J.-M. Lehn:Proc. Natl. Acad. Sci. USA
80, ).139.R. Frank and H. Rau:Z. Naturforsch.
37A, ).140.I. Tabushi and S.-i. Kugimiya.J. Am. Chem. Soc.
107, ).141.S. Shinkai and O. Manabe:Topics Curr Chem.
121, 67 (1984).142.D. W. Urry:Topics Curr. Chem.
128, 175 (1985).143.R. Nagaraj and P. Balaram:Acc. Chem. Res.
14, 356 (1981); R. O. Fox, Jr. and F. M. Richards:Nature
300, 325 (1982).144.J.-P. Behr, J.-M. Lehn, A.-C. Dock and D. Moras:Nature
295, 526 (1982).145.U. F. Kragten, M. F. M. Roks and R. J. M. Nolte:J. Chem. Soc., Chem. Commun. .146.I. Tabushi, Y. Kuroda and K. Yokota:Tetrahedron Lett. .147.J.-H. Fuhrhop and U. Liman:J. Am. Chem. Soc.
106, ).148.J.-H. Fufrhop, U. Liman and H. H. David:Angew. Chem. Int. Ed. Engl.
24, 339 (1985).149.J.-H. Lehn and J. Simon:Helv. Chim. Acta
60, 141 (1977).150.J.-H. Lehn and M. E. Stubbs:J. Am. Chem. Soc.
96, ).151.W. Fischer, J. Brickmann and P. Lauger:Biophys. Chem.
13, 105 (1981).152.C. Etchebest, S. Ranganathan and A. Pullman:IEBS Letters
173, 301 (1984).153.For an earlier use of the intersection sign, see: E. Kauffmann, J. L. Dye, J.-M. Lehn and A. I. Popov:J. Am. Chem. Soc.
102, ).154.A. G. Amit, R. A. Mariuzza, S. E. V. Phillips and R. J. Poljak:Science
233, 747 (1986); H. M. Geysen, J. A. Tainer, S. J. Rodda, T. J. Mason, H. Alexander, E. D. Getzoff and R. A. Libid. Science
235, )155.M. M. Harding and J.-M. Lehn: unpublished work.156.D. A. Tomalia, M. Hall and D. M. Hedstrand:J. Am. Chem. Soc.
109, ) and references therein.157.G. R. Newkome, Z.-q. Yao, G. R. Baker, V. K. Gupta, P. S. Russo and M. J. Saunders:J. Am. Chem. Soc.
108, 849 (1986); G. R. Newkome, G. R. Baker, M. J. Saunders, P. S. Russo, V. K. Gupta, Z.-q. Yao, J. E. Miller and K. Bouillion:J. Chem. Soc., Chem. Commun. .158.H. M. McConnell, L. K. Tamm and R. M. Weiss:Proc. Natl. Acad. Sci. USA
81, ): R. M. Weiss and H. M. McConnell:Nature
310, 47 (1984).159.T. Kunitake, Y. Okahata, M. Shimomura, S.-i. Yasunami and K. Takarabe:J. Am. Chem. Soc.
103, ); N. Nakashima, S. Asakuma andT. Kunitake:ibid. J. Am. Chem. Soc.
107 (.160.J. H. Fendler:Membrane Mimetic Chemistry, Wiley, New York, 1982.161.H. Kuhn and D. Moebius:Angew. Chem. Int. Ed. Engl.
10, 620 (1971).162.D. Moebius:Acc. Chem. Res.
14, 63 (1981):Ber. Bunsenges Phys. Chem.
82, 848 (1978);Z. Physik. Chem. Neue Folge
154, 121 (1987).163.J. A. Hayward (Ed.):New Technological Applications of Phospholipid Bilayers, Thin Films and Vesicles, Tenerife, January 6–9, 1986, Plenum Press.164.J. Sagiv: in [163]; L. Netzer and J. Sagiv:J. Am. Chem. Soc.
105, 674 (1983).165.H.-H. Hub, B. Hupfer, H. Koch and H. Ringsdorf:Angew. Chem. Int. Ed. Engl.
19, 938 (1980); L. Gros, H. Ringsdorf and H. Schupp:ibid. Angew. Chem. Int. Ed. Engl.
20, 305 (1981).166.G. Wegner:Chimia
36, 63 (1982); C. M. Paleos:Chem. Soc. Rev.
14, 45 (1985).167.H. Kuhn:Pure Appl. Chem.
53, ).168.(a)J.-H. Fufrhop and J. Mathieu:Angew. Chem. Int. Ed. Engl.
23, 100 (1984);168(b).J.-H. Fuhrhop and D. Fritsch:Acc. Chem. Res.
19, 130 (1986);168(c).Y. Okahata:Acc. Chem. Res.
19, 57 (1986).169.(a)B. Balzani (Ed.):Supramolecular Photochemistry, D. Reidel Publ. Co., Dordrecht, Holland, 1987;169.(b)J.-M. Lehn: p. 29 therein.170.J.-C. Rodriguez-Ubis, B. Alpha, D. Plancherel and J.-M. Lehn:Helv. Chim. Acta
67, ).171.B. Alpha, J.-M. Lehn and G. Mathis:Angew. Chem. Int. Ed. Engl.
26, 266 (1987); B. Alpha, V. Balzani, J.-M. Lehn, S. Perathoner and N. Sabbatini:Angew. Chem. Int. Ed. Engl.
26 (1987), N. Sabbatini, S. Perathoner, V. Balzani, B. Alpha and J.-M. Lehn, in ref. [169a], p. 187.172.(a)H. Bouas-Laurent, A. Castellan and J.-P. Desvergne:Pure Appl. Chem.
52, );172.(b)H. Bouas-Laurent, A. Castellan, M. Daney, J.-P. Desvergne, G. Guinand, P. Marsau and M.-H. Riffaud:J. Am. Chem. Soc.
108, 315 (1986).173.J. P. Konopelski, F. Kotzyba-Hibert, J.-M. Lehn, J.-P. Desvergne, F. Fagès, A. Castellan and H. Bouas-Laurent:J. Chem. Soc., Chem. Commun.
1985, 433.174.D. F. Eaton:Tetrahedron
43, ) and references therein.175.A. Guarino.J. Photochem.
35, 1 (1986).176.M. Gubelmann, J.-M. Lehn, J. L. Sessler and A. Harriman: to be published.177.V. Balzani, N. Sabbatini and F. Scandola:Chem. Rev.
86, 319 (1986).178.Photoactive units may photooxidise complexed substrates, [93] and effect DNA photocleavage: A. J. Blacker, J. Jazwinski, J.-M. Lehn and F.-X. Wilhelm:J. Chem. Soc., Chem. Commun. .179.(a)J.-M. Lehn, in D. S. Chemla and J. Zyss (Eds.):Non-Linear Optical Properties of Organic Molecules and Crystals, Academic Press, New York, vol. 1987, p. 215;179.(b)J. F. Nicoud and R. J. Twieg:ibidin D. S. Chemla and J. Zyss (Eds.):Non-Linear Optical Properties of Organic Molecules and Crystals, Academic Press, New York, vol. 1987, p. 221.180.M. Takagi and K. Ueno:Topics Curr. Chem.
121, 39 (1984); H.-G. Lohr and F. V?gtle:Acc. Chem. Res.
18, 65 (1985); R. Klink, D. Boaart, J.-M. Lehn, B. Helfert and R. Bitsch: Merck GmbH, Eur. Patent Appl.
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82, ); R. W. Munn:Chem. Br. ; J. Simon, J.-J. André and A. Skoulios:Nouv. J. Chim.
10, 295 (1986); J. Simon, F. Tournilhac and J.-J. André:ibid Nouv. J. Chim.
11, 383 (1987) and references therein.182.T. S. Arrhenius, M. Blanchard-Desce, M. Dvolaitzky, J.-M. Lehn and J. Malthete:Proc. Natl. Acad. Sci. USA
83 ).183.(a)Biological effectors may also be sought: I. Tabushi, T. Nishiya, M. Shimomura, T. Kunitake, H. Inokuchi and T. Yagi:J. Am. Chem. Soc.
106, 219 (1984);183.(b)for other related work see for instance: J. K. Nagle, J. S. Bernstein, R. C. Young and T. J. Meyer:Inorg. Chem.
20, ); E. T. T. Jones, O. M. Chyan and M. S. Wrighton:J. Am. Chem. Soc.
109, ).184.R. Schwyzer, A. Tun-Kyi, M. Caviezel and P. Moser:Helv. Chim. Acta
53, 15 (1970);Experientia
26, 577 (1970); see also ref. [1] p. 19.185.(a)S. Shinkai:Pure Appl. Chem.
59, 425 (1987);185.(b)D. A. Gustowski, M. Delgado, V. J. Gatto, L. Echegoyen and G. W. Gokel:J. Am. Chem. Soc.
108, ) and references therein.186.J.-M. Lehn, J. Malthête and A.-M. Levelut:J. Chem. Soc., Chem. Commun. .187.For phthalocyanine derived columnar mesophases see D. Masurel, C. Sirlin and J. Simon:New J. Chem.
11, 455 (1987) and references therein.188.E. Carafoli and J. T. Penniston:Sci. Amer. November 50 (1985); T. Hiraoki and H. J. Vogel:J. Cardiovasc. Pharm.
10, (Suppl. 1), S14 (1987).189.I. Tabushi, S.-i. Kugimiya and T. SasakiJ. Am. Chem. Soc.
107, ) and references therein.190.D. P?rschke and M. Eigen:J. Mol. Biol.
62, 361 (1971) and references therein.191.J.-M. Lehn, A. Rigault, J. Siegel, J. Harrowfield, B. Chevrier and D. Moras:Proc. Natl. Acad. Sci. USA
84, (; J.-M. Lehn and A. Rigault, unpublished results.192.K. E. Drexler:Proc. Natl. Acad. Sci. USA
78, ); C. Joachim and J.-P. Launay:Nouv. J. Chim.
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