A New Macrobicyclic Tris‐bipyridine Ligand and Its Cu and Ag Complexes
1991; Wiley; Volume: 30; Issue: 10 Linguagem: Inglês
10.1002/anie.199113311
ISSN1521-3773
AutoresJavier de Mendoza, Esther Mesa, Juan‐Carlos Rodríguez‐Ubis, Purificación Vázquez, Fritz Vögtle, P.‐M. WINDSCHEIF, Kari Rissanen, Jean‐Maríe Lehn, Daniel Lilienbaum, Raymond Ziessel,
Tópico(s)Supramolecular Chemistry and Complexes
ResumoAngewandte Chemie International Edition in EnglishVolume 30, Issue 10 p. 1331-1333 Communication A New Macrobicyclic Tris-bipyridine Ligand and Its Cu and Ag Complexes† Prof. Dr. Javier de Mendoza, Corresponding Author Prof. Dr. Javier de Mendoza Departamento de Química, Universidad Autónoma de Madrid, Cantoblanco, E-28049 Madrid (Spain) Javier de Mendoza, Institut für Organische Chemie und Biochemie der Universität, Gerhard-Domagk-Strasse 1, W-5300 Bonn 1 (FRG) Fritz Vögtle, Institut für Organische Chemie und Biochemie der Universität, Gerhard-Domagk-Strasse 1, W-5300 Bonn 1 (FRG) Jean-Maríe Lehn, Institut Le Bel, Université Louis Pasteur, 4, rue Blaise Pascal, F-67000 Strasbourg (France)Search for more papers by this authorEsther Mesa, Esther Mesa Departamento de Química, Universidad Autónoma de Madrid, Cantoblanco, E-28049 Madrid (Spain)Search for more papers by this authorDr. Juan-Carlos Rodríguez-Ubis, Dr. Juan-Carlos Rodríguez-Ubis Departamento de Química, Universidad Autónoma de Madrid, Cantoblanco, E-28049 Madrid (Spain)Search for more papers by this authorDr. Purificación Vázquez, Dr. Purificación Vázquez Departamento de Química, Universidad Autónoma de Madrid, Cantoblanco, E-28049 Madrid (Spain)Search for more papers by this authorProf. Dr. Fritz Vögtle, Corresponding Author Prof. Dr. Fritz Vögtle Institut für Organische Chemie und Biochemie der Universität, Gerhard-Domagk-Strasse 1, W-5300 Bonn 1 (FRG) Javier de Mendoza, Institut für Organische Chemie und Biochemie der Universität, Gerhard-Domagk-Strasse 1, W-5300 Bonn 1 (FRG) Fritz Vögtle, Institut für Organische Chemie und Biochemie der Universität, Gerhard-Domagk-Strasse 1, W-5300 Bonn 1 (FRG) Jean-Maríe Lehn, Institut Le Bel, Université Louis Pasteur, 4, rue Blaise Pascal, F-67000 Strasbourg (France)Search for more papers by this authorDipl.-Chem. Paul-Michael Windscheif, Dipl.-Chem. Paul-Michael Windscheif Institut für Organische Chemie und Biochemie der Universität, Gerhard-Domagk-Strasse 1, W-5300 Bonn 1 (FRG)Search for more papers by this authorPriz.-Doz. Dr. Kari Rissanen, Priz.-Doz. Dr. Kari Rissanen Department of Chemistry, University of Jyväskylä, Kyllikinatu 1-3, SF-40100 Jyväskylä (Finland)Search for more papers by this authorProf. Dr. Jean-Maríe Lehn, Corresponding Author Prof. Dr. Jean-Maríe Lehn Institut le Bel, Université Louis Pasteur, 4, rue Blaise Pascal, F-67000 Strasbourg (France) Javier de Mendoza, Institut für Organische Chemie und Biochemie der Universität, Gerhard-Domagk-Strasse 1, W-5300 Bonn 1 (FRG) Fritz Vögtle, Institut für Organische Chemie und Biochemie der Universität, Gerhard-Domagk-Strasse 1, W-5300 Bonn 1 (FRG) Jean-Maríe Lehn, Institut Le Bel, Université Louis Pasteur, 4, rue Blaise Pascal, F-67000 Strasbourg (France)Search for more papers by this authorDaniel Lilienbaum, Daniel Lilienbaum Institut le Bel, Université Louis Pasteur, 4, rue Blaise Pascal, F-67000 Strasbourg (France)Search for more papers by this authorDr. Raymond Ziessel, Dr. Raymond Ziessel Institut le Bel, Université Louis Pasteur, 4, rue Blaise Pascal, F-67000 Strasbourg (France)Search for more papers by this author Prof. Dr. Javier de Mendoza, Corresponding Author Prof. Dr. Javier de Mendoza Departamento de Química, Universidad Autónoma de Madrid, Cantoblanco, E-28049 Madrid (Spain) Javier de Mendoza, Institut für Organische Chemie und Biochemie der Universität, Gerhard-Domagk-Strasse 1, W-5300 Bonn 1 (FRG) Fritz Vögtle, Institut für Organische Chemie und Biochemie der Universität, Gerhard-Domagk-Strasse 1, W-5300 Bonn 1 (FRG) Jean-Maríe Lehn, Institut Le Bel, Université Louis Pasteur, 4, rue Blaise Pascal, F-67000 Strasbourg (France)Search for more papers by this authorEsther Mesa, Esther Mesa Departamento de Química, Universidad Autónoma de Madrid, Cantoblanco, E-28049 Madrid (Spain)Search for more papers by this authorDr. Juan-Carlos Rodríguez-Ubis, Dr. Juan-Carlos Rodríguez-Ubis Departamento de Química, Universidad Autónoma de Madrid, Cantoblanco, E-28049 Madrid (Spain)Search for more papers by this authorDr. Purificación Vázquez, Dr. Purificación Vázquez Departamento de Química, Universidad Autónoma de Madrid, Cantoblanco, E-28049 Madrid (Spain)Search for more papers by this authorProf. Dr. Fritz Vögtle, Corresponding Author Prof. Dr. Fritz Vögtle Institut für Organische Chemie und Biochemie der Universität, Gerhard-Domagk-Strasse 1, W-5300 Bonn 1 (FRG) Javier de Mendoza, Institut für Organische Chemie und Biochemie der Universität, Gerhard-Domagk-Strasse 1, W-5300 Bonn 1 (FRG) Fritz Vögtle, Institut für Organische Chemie und Biochemie der Universität, Gerhard-Domagk-Strasse 1, W-5300 Bonn 1 (FRG) Jean-Maríe Lehn, Institut Le Bel, Université Louis Pasteur, 4, rue Blaise Pascal, F-67000 Strasbourg (France)Search for more papers by this authorDipl.-Chem. Paul-Michael Windscheif, Dipl.-Chem. Paul-Michael Windscheif Institut für Organische Chemie und Biochemie der Universität, Gerhard-Domagk-Strasse 1, W-5300 Bonn 1 (FRG)Search for more papers by this authorPriz.-Doz. Dr. Kari Rissanen, Priz.-Doz. Dr. Kari Rissanen Department of Chemistry, University of Jyväskylä, Kyllikinatu 1-3, SF-40100 Jyväskylä (Finland)Search for more papers by this authorProf. Dr. Jean-Maríe Lehn, Corresponding Author Prof. Dr. Jean-Maríe Lehn Institut le Bel, Université Louis Pasteur, 4, rue Blaise Pascal, F-67000 Strasbourg (France) Javier de Mendoza, Institut für Organische Chemie und Biochemie der Universität, Gerhard-Domagk-Strasse 1, W-5300 Bonn 1 (FRG) Fritz Vögtle, Institut für Organische Chemie und Biochemie der Universität, Gerhard-Domagk-Strasse 1, W-5300 Bonn 1 (FRG) Jean-Maríe Lehn, Institut Le Bel, Université Louis Pasteur, 4, rue Blaise Pascal, F-67000 Strasbourg (France)Search for more papers by this authorDaniel Lilienbaum, Daniel Lilienbaum Institut le Bel, Université Louis Pasteur, 4, rue Blaise Pascal, F-67000 Strasbourg (France)Search for more papers by this authorDr. Raymond Ziessel, Dr. Raymond Ziessel Institut le Bel, Université Louis Pasteur, 4, rue Blaise Pascal, F-67000 Strasbourg (France)Search for more papers by this author First published: October 1991 https://doi.org/10.1002/anie.199113311Citations: 77 † This work was supported by Comisión Interministerial de Ciencia y Tecnología (CICYT PB87-0109), by the Bundesministerium für Forschung und Technologie (BMFT-0329120A), by the CNRS (URA 422) and by the Academy of Finland (No. 1031 002). Since our three groups in Madrid, Bonn, and Strasbourg, supplemented by a Finnish group, had been working independently on this same topic, we decided to publish our results jointly, in a European spirit! AboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onEmailFacebookTwitterLinkedInRedditWechat Graphical Abstract The novel cage ligand of Ag-cryptate 1 is formed in a one-pot synthesis through condensation of the corresponding bipyridinedialdehyde with tris(2-aminoethy1)amine in greater than 70 % yield. The cryptate 1 is the first Ag1 complex in which three Ag1 ions are direct neighbors within the same cavity. All 14 N atoms of the ligand are involved in coordination. Drastic conformational changes during complexation, particularly for the trisbipyridine fragment, were revealed by X-ray structure analyses of the cage ligand and of 1. References 1 J. E. Prue, G. Schwarzenbach, Helv. Chim. Acta 33 (1950) 963. 2(a) J.-M. Lehn, S. H. Pine, E. Watanabe, A. K. Willard, J Am. Chem. Soc. 99 (1977) 676; (b) B. Dietrich, M. W. Hosseini, J.-M. Lehn, R. B. Sessions, Helv. Chim. Acta 68 (1985) 289; (c) R. J. Motekaitis, A. E. Martell, I. Murase, J.-M. Lehn, M. W. Hosseini, Inorg. Chem. 27 (1988) 3630. 3(a) J. Jazwinski, J.-M. Lehn, D. Lilienbaum, R. Ziessel, J. Guilhem, C. Pascard, J. Chem. Soc. Chem. Cornmun. 1987, 1691; (b) J.-M. Lehn, R. Meric, J.-P. Vigneron, I. Bkouche-Waksman, C. Pascard, J. Chem. Soc. Chem. Cornmun. 1991, 62; (c) D. MacDowell, J. Nelson, Tetrahedron Lett. 29 (1988) 385; (d) D. Mac-Dowell, J. Nelson, V. McKee, Polyhedron 8 (1989) 1143; (e) O. Kocian, R. J. Mortimer, P. D. Beer, Tetrahedron Lett. 31 (1990) 5069. 4(a) See for instance: K. Kalyanasundaram, Coord. Chem. Rev. 46 (1982) 159; (b) A. Juris, V. Balzani, F. Barigelleti, S. Campagna, P. Belser, A. von Zelewsky, Coord. Chem. Rev. 84 (1988) 85; (c) F. Barigelleti, L. de Cola, V. Balzani, P. Belser, A. von Zelewsky, F. Vögtle, F. Ebmeyer, S. Grammenudi, J. Am. Chem. Soc. 111 (1989) 4662. 5 F. Ebmeyer, F. Vögtle, Chem. Ber. 122 (1989) 1725. 6 A. J. Mancuso, D. Swern, Synthesis 1981, 165. 7 B. J. Hathaway, D. G. Holah, J. D. Postlethwaite, J. Chem. Soc. 1961, 3215. 8Crystal structure data for 3: C48H48N144 H2O, colorless crystals. monoclinic, space group P21/c (No. 14); Mr = 893. 06; a = 1721. 6(3), b = 1631. 0(2), c = 1719. 6(3) pm, β = 97. 98 (4)°; V = 4782(1) × 106 pm3, Z = 4; ϱcalcd = 1.241 g cm−3; Cukα (λ = 1. 5418 Å); μ = 0. 63 mm−1; F(000) = 1896; T = 296 ± 1 K; crystal dimensions, 0. 20 × 0. 20 × 0. 30 mm; CAD4 diffractometer (Enraf Nonius); corrections: Lorentz polarization, linear ca. 45% decrease (corrected with factors 1. 00 to 1. 53 on I), empirical absorption correction (DIFABS) with minimum and maximum correction coeficients 0. 884 and. 1. 254; 2θ = 4–100°; hkl range h = −1 → 17, k = −1 → 16, l = −17 → 17; 6085 measured, 4918 unique reflections, 3642 with I > 2.0 σ(I). The structure was solved using SHELXS. Refinement: full-matrix least-squares, R = 0.053, Rw = 0. 061 (w = w′[1. 0 -(Δ F/6. σ F)2]2, with w′ = Chebychev polynomial for Fc, with three coefficients (10. 8, 4. 3 and 7. 95)), Rint = 0. 020. Crystal structure data for 6: [C48H48N14Ag3] (BF4)3 pale yellow crystals, triclinic, space group P-1 (No. 2); Mr = 1405. 02; a = 1358. 0(1), b = 1433. 3(3), c = 1576. 7(2) pm, α = 106. 95(1), β = 99. 98(1), γ = 82. 99(1)°; V = 2894(1) × 106 pm3, Z = 2; ϱcaled = 1. 612 gcm−3 Cukα (λ = 1. 5418 Å); μ = 8.97mm−1; F(000) = 1396; T = 296 ± 1 K; crystal dimensions, 0.15 × 0. 15 × 0. 20 mm; CAD4 diffractometer (Enraf Nonius); corrections: Lorentz polarization, empirical absorption correction (DIFABS) with minimum and maximum correction coefficients 0. 759 and 1. 532; 2θ = 4–130°; hkl range h = −1 → 15, k = −16 → 16, l = −18 → 18; 10488 measured, 9596 unique reflections, 5415 with I > 3.0 σ(I). The structure was solved using SHELXS. Refinement: block-matrix least-squares (three blocks), R = 0. 058, R = 0. 070 (w = w′[1. 0-(Δ F/6. σF)2]2, with w′ = Chebychev polynominal for Fc with three coefficients (16. 3, −0. 097 and 12. 9)), Rint = 0. 045. Non-hydrogen atoms refined anisotropically, H atoms calculated at their idealized positions (CH distance 1. 00 Å) and included in the final structure factor calculations but not refined (CRYSTALS and PLUTO programs). Further details of the crystal structure investigations are available on request from the Director of the Cambridge Crystallographic Data Centre, University Chemical Laboratory, Lensfield Road, GB-Cambridge CB2 1 EW (UK), on quoting the full journal citation. 9 The energy difference (steric energy) between the two conformations of the free ligand 3 and the conformation of the tris-AgI complex 6 calculated by MM2 can be estimated to be approximately 57 kJ mol−1 [on an HP9000 model 825SSRX; as option of the molecular modeling program MOLEK9000 (version February 1991). P. Bischof, ISKA (Bensheim)]. 10(a) J. C. Rodríguez-Ubis, B. Alpha, D. Plancherel, J.-M. Lehn, Helv. Chim. Acta 67 (1984) 2264; (b) B. Alpha, Thèse de Doctorat des Sciences, Univeristé Louis Pasteur, Strasbourg, 1987. Citing Literature Volume30, Issue10October 1991Pages 1331-1333 ReferencesRelatedInformation
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