A Calix[4]imidazolium[2]pyridine as an Anion Receptor†
Kavitha Chellappan Dr.
National Creative Research Initiative Center for Superfunctional Materials, Department of Chemistry, Division of Molecular and Life Sciences, Pohang University of Science and Technology, Pohang 790-784, Korea, Fax: (+82) 54-279-8137
contributed equally to this work.
Search for more papers by this authorN. Jiten Singh
National Creative Research Initiative Center for Superfunctional Materials, Department of Chemistry, Division of Molecular and Life Sciences, Pohang University of Science and Technology, Pohang 790-784, Korea, Fax: (+82) 54-279-8137
contributed equally to this work.
Search for more papers by this authorIn-Chul Hwang Prof.
National Creative Research Initiative Center for Superfunctional Materials, Department of Chemistry, Division of Molecular and Life Sciences, Pohang University of Science and Technology, Pohang 790-784, Korea, Fax: (+82) 54-279-8137
Search for more papers by this authorJung Woo Lee
National Creative Research Initiative Center for Superfunctional Materials, Department of Chemistry, Division of Molecular and Life Sciences, Pohang University of Science and Technology, Pohang 790-784, Korea, Fax: (+82) 54-279-8137
Search for more papers by this authorKwang S. Kim Prof.
National Creative Research Initiative Center for Superfunctional Materials, Department of Chemistry, Division of Molecular and Life Sciences, Pohang University of Science and Technology, Pohang 790-784, Korea, Fax: (+82) 54-279-8137
Search for more papers by this authorKavitha Chellappan Dr.
National Creative Research Initiative Center for Superfunctional Materials, Department of Chemistry, Division of Molecular and Life Sciences, Pohang University of Science and Technology, Pohang 790-784, Korea, Fax: (+82) 54-279-8137
contributed equally to this work.
Search for more papers by this authorN. Jiten Singh
National Creative Research Initiative Center for Superfunctional Materials, Department of Chemistry, Division of Molecular and Life Sciences, Pohang University of Science and Technology, Pohang 790-784, Korea, Fax: (+82) 54-279-8137
contributed equally to this work.
Search for more papers by this authorIn-Chul Hwang Prof.
National Creative Research Initiative Center for Superfunctional Materials, Department of Chemistry, Division of Molecular and Life Sciences, Pohang University of Science and Technology, Pohang 790-784, Korea, Fax: (+82) 54-279-8137
Search for more papers by this authorJung Woo Lee
National Creative Research Initiative Center for Superfunctional Materials, Department of Chemistry, Division of Molecular and Life Sciences, Pohang University of Science and Technology, Pohang 790-784, Korea, Fax: (+82) 54-279-8137
Search for more papers by this authorKwang S. Kim Prof.
National Creative Research Initiative Center for Superfunctional Materials, Department of Chemistry, Division of Molecular and Life Sciences, Pohang University of Science and Technology, Pohang 790-784, Korea, Fax: (+82) 54-279-8137
Search for more papers by this authorThis work was supported by CRI (KOSEF/MOST) and BK21. We thank Prof. F. P. Schmidtchen for his help with the data analysis and Prof. C. S. Wilcox for allowing us access to the HOSTEST program.
Graphical Abstract
Ein effektives makrocyclisches Ionophor für F−-Ionen, das aus einer Anordnung positiv geladener Imidazoliumeinheiten besteht, wurde hergestellt. Das Calix[4]imidazolium[2]pyridin-Kation bildet mit F−-Ionen einen 1:1-Komplex, wie Bindungsstudien mithilfe der 1H-NMR-Spektroskopie, die Kristallstrukturbestimmung (siehe Bild) und Dichtefunktionalrechnungen belegen.
Supporting Information
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References
- 1
- 1aP. de Hoog, P. Gamez, I. Mutikainen, U. Turpeinen, J. Reedijik, Angew. Chem. 2004, 116, 5939–5941;
10.1002/ange.200460486 Google ScholarAngew. Chem. Int. Ed. 2004, 43, 5815–5817;
- 1bJ. L. Sessler, D. Seidel, Angew. Chem. 2003, 115, 5292–5333;
10.1002/ange.200200561 Google ScholarAngew. Chem. Int. Ed. 2003, 42, 5134–5175;
- 1cP. D. Beer, P. A. Gale, Angew. Chem. 2001, 113, 502–532;
10.1002/1521-3757(20010202)113:3<502::AID-ANGE502>3.0.CO;2-A Google ScholarAngew. Chem. Int. Ed. 2001, 40, 486–516;10.1002/1521-3773(20010202)40:3<486::AID-ANIE486>3.0.CO;2-P CAS PubMed Web of Science® Google Scholar
- 1d Supramolecular chemistry of anions (Eds.: ), Wiley-VCH, New York, 1997;
- 1eJ. Y. Kwon, N. J. Singh, H. N. Kim, S. K. Kim, K. S. Kim, J. Yoon, J. Am. Chem. Soc. 2004, 126, 8892–8893;
- 1fF. P. Schmidtchen, M. Berger, Chem. Rev. 1997, 97, 1609–1646.
- 2
- 2aC. R. Bondy, P. A. Gale, S. J. Loeb, J. Am. Chem. Soc. 2004, 126, 5030–5031;
- 2bM. J. Chmielewski, M. Charon, J. Jurczak, Org lett. 2004, 6, 3501–3504;
- 2cK. A. Nielsen, J. O. Jeppesen, E. Levillain, J. Becher, Angew. Chem. 2003, 115, 197–201;
10.1002/ange.200390042 Google ScholarAngew. Chem. Int. Ed. 2003, 42, 187–191;
- 2dE. J. Cho, J. W. Moon, S. W. Ko, J. Y. Lee, S. K. Kim, J. Yoon, K. C. Nam, J. Am. Chem. Soc. 2003, 125, 12 376–12 377;
- 2eK. J. Wallace, W. J. Belcher, K. F. Syed, J. W. Seed, J. Am. Chem. Soc. 2003, 125, 9699–9715;
- 2fT. Mizuno, W.-H. Wei, L. R. Eller, J. L. Sessler, J. Am. Chem. Soc. 2002, 124, 1134–1135;
- 2gM. Haj-Zaroubi, N. W. Mitzel, F. P. Schmidtchen, Angew. Chem. 2002, 114, 111–114;
10.1002/1521-3757(20020104)114:1<111::AID-ANGE111>3.0.CO;2-P Google ScholarAngew. Chem. Int. Ed. 2002, 41, 104–107;10.1002/1521-3773(20020104)41:1<104::AID-ANIE104>3.0.CO;2-Z CAS PubMed Web of Science® Google Scholar
- 2hF. P. Schmidtchen, Org. Lett. 2002, 4, 431–434;
- 2iG. Cafeo, F. H. Kohnke, G. L. La Torre, A. J. P. White, D. J. Williams, Angew. Chem. 2000, 112, 1556–1558;
10.1002/(SICI)1521-3757(20000417)112:8<1556::AID-ANGE1556>3.0.CO;2-B Google ScholarAngew. Chem. Int. Ed. 2000, 39, 1496–1498;10.1002/(SICI)1521-3773(20000417)39:8<1496::AID-ANIE1496>3.0.CO;2-I CAS PubMed Web of Science® Google Scholar
- 2jM., Sirish, H.-J. Schneider, J. Am. Chem. Soc. 2000, 122, 5881–5882;
- 2kK. Niikura, A. P. Bisson, E. V. Anslyn, J. Chem. Soc. Perkin Trans. 2 1999, 1111–1114.
- 3
- 3aS. K. Kim, N. J. Singh, S. J. Kim, H. G. Kim, J. K. Kim, J. W. Lee, K. S. Kim, J. Yoon, Org. Lett. 2003, 5, 2083–2086;
- 3bS. Yun, H. Ihm, H. G. Kim, C. W. Lee, B. Indrajit, K. S. Oh, Y. J. Gong, J. W. Lee, J. Yoon, H. C. Lee, K. S. Kim, J. Org. Chem. 2003, 68, 2467–2470;
- 3cH. Ihm, S. Yun, H. G. Kim, J. K. Kim, K. S. Kim, Org. Lett. 2002, 4, 2897–2900;
- 3dK. Sato, S. Arai, T. Yamagishi, Tetrahedron Lett. 1999, 40, 5219–5222.
- 4
- 4aK. A. Nielsen, W.-S. Cho, J. O. Jeppensen, V. M. Lynch, J. Becher, J. Sessler, J. Am. Chem. Soc. 2004, 126, 16 296–16 297;
- 4bP. Piatek, V. M. Lynch, J. L. Sessler, J. Am. Chem. Soc. 2004, 126, 16 073–16 076;
- 4cJ. L. Sessler, V. Krol, T. V. Shishkanova, P. A. Gale, Proc. Natl. Acad. Sci. USA 2002, 99, 4848–4853;
- 4dC. Bucher, R. S. Zimmerman, V. Lynch, J. L. Sessler, J. Am. Chem. Soc. 2001, 123, 9716–9717;
- 4eP. A. Gale, J. L. Sessler, V. Král, V. Lynch, J. Am. Chem. Soc. 1996, 118, 5140–5141.
- 5
- 5aS. O. Kang, J. M. Llinares, D. VanderVelde, K. Bowman-James, J. Am. Chem. Soc. 2003, 125, 10 152–10 153;
- 5bC. J. Woods, S. Camiola, M. E. Light, S. J. Coles, M. B. Hursthouse, M. A. King, P. A. Gale, J. W. Essex, J. Am. Chem. Soc. 2002, 124, 8644–8652;
- 5cM. Takeuchi, T. Shioya, T. M. Swager, Angew. Chem. 2001, 113, 3372–3376;
Angew. Chem. Int. Ed. 2001, 40, 3372–3376;
10.1002/1521-3773(20010917)40:18<3372::AID-ANIE3372>3.0.CO;2-1 CAS PubMed Web of Science® Google Scholar
- 5dP. Anzenbacher, K. Jursikova, J. L. Sessler, J. Am. Chem. Soc. 2000, 122, 9350–9351.
- 6C. S. Wilcox in Frontiers in Supramolecular Organic Chemistry and Photochemistry (Eds.: ), VCH, Weinheim, 1991, pp. 123–143.
- 7Crystallographic data for 1-Br4⋅6 H2O: triclinic, space group P
, a=7.281(7), b=10.693(1), c=12.749(1) Å, α=71.270(2), β=80.668(2), γ=83.539(2)°, V=925.6(1) Å3, Z=1, GOF=1.001, R1=0.030, wR2=0.0765. 1-(PF6)4⋅CH3CN: triclinic, space group P
, a=7.905(1), b=11.993(1), c=12.597(1) Å, α=108.540(2), β=99.468(2), γ=98.131(2)°, V=1092.6(2) Å3, Z=1, GOF=1.067, R1(I>2σ(I))=0.0664, wR2=0.1838. 1-Cl4⋅5 H2O: triclinic, space group P
, a=7.219(1), b=10.55(1), c=11.805(1) Å, α=100.637(2), β=93.709(2), γ=101.095(2)°, V=862.3(1) Å3, Z=1, GOF=1.100, R1(I>2σ(I))=0.0282, wR2=0.0782. 1-F(PF6)3⋅2 H2O: monoclinic, space group Cm, a=13.901(2), b=20.921(3), c=8.504(1) Å, β=93.709(2)°, V=2085.8(5) Å3, Z=2, GOF=1.058, R1(I>2σ(I))=0.0835, wR2=0.2208. 1-Cl2(PF6)2⋅2 MeCN: triclinic, space group P
, a=8.496(1), b=11.494(2), c=12.072(2) Å, α=80.212(3), β=71.576(3), γ=69.760(3)°, V=1047.0(3) Å3, Z=1, GOF=0.996, R1(I>2σ(I))=0.0933, wR2=0.1187. {1-Br2(PF6)2}{1-(PF6)4}: triclinic, space group P
, a=12.201(1), b=14.143(1), c=14.204(1) Å, α=96.825(2), β=109.519(1), γ=90.931(2)°, V=2291.3(3) Å3, Z=2, GOF=0.951, R1(I>2σ(I))=0.0657, wR2=0.0963. CCDC-234170–234172 and -259317–259319 contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
- 8
- 8aJ. Kim, H. M. Lee, S. B. Suh, D. Majumdar, K. S. Kim, J. Chem. Phys. 2000, 113, 5259–5272;
- 8bH. M. Lee, D. Kim, K. S. Kim, J. Chem. Phys. 2002, 116, 5509–5520;
- 8cK. S. Kim, P. Tarakeshwar, J. Y. Lee, Chem. Rev. 2000, 100, 4145–4186.
- 9J. R. Blas, M. Marquez, J. L. Sessler, F. J. Luque, M. Orozco, J. Am. Chem. Soc. 2002, 124, 12 796–12 805.
- 10
- 10aJ. Ruiz, M. E. G. Mosquera, G. García, F. Marquinez, V. Riera, Angew. Chem. 2005, 117, 104–107; Angew. Chem. Int. Ed. 2005, 44, 102–105;
- 10bX. Hu, I. Castro-Rodriguez, K. Meyer, Organometallics, 2003, 22, 3016–3018;
- 10cW. A. Herrmann, Angew. Chem. 2002, 114, 1326–1341;
Angew. Chem. Int. Ed. 2002, 41, 1290–1309.
10.1002/1521-3773(20020415)41:8<1290::AID-ANIE1290>3.0.CO;2-Y CAS PubMed Web of Science® Google Scholar
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