Synthesis of original capping calixarenes with DTPA fragment

Journal of Inclusion Phenomena and Macrocyclic Chemistry

Volumn 61, Issue 1-2, 2008, Pages 187-193

  Lin, Yi ^a,b,c,d,e,f   Leydier, Antoine ^a,b,c,d,e,f   Métay, Estelle ^a,b,c,d,e,f   Favre Réguillon, Alain ^a,b,c,d,e,f   Bouchu, Denis ^a,b,c,d,e,f   Pellet Rostaing, Stéphane ^a   Lemaire, Marc ^a,b,c,d,e,f  

^a UNIVERSITÉ LYON 1   (France)

^b CNRS   (France)

^c UNIVERSITÉ DE LYON   (France)

^d UNIVERSITÉ LYON 1   (France)

^e UNIVERSITÉ DE LYON   (France)

^f CPE LYON   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 43949107512     PISSN: 09230750     EISSN: None     Source Type: Journal    
DOI: 10.1007/s10847-008-9413-9     Document Type: Article

References (20)

1. 1. (a) Gutsche, C.D.: Calixarenes, Monographs in Supramolecular Chemistry, Series Ed. Stoddart, J.F. Royal society of chemistry, Cambridge (1989); (b) Shinkai S Calixarene as the third supramolecular host In: Gokel GW (ed) Advances in supramolecular chemistry, vol. 3, pp. 97–130. J. Press Inc (1993); (c) Gutsche, C.D.: In: Stoddart, J.F. (ed.) Calixarenes revisited, Monographs in Supramolecular Chemistry, vol. 6. The Royal Society, Cambridge (1998); (d) Asfari, Z., Böhmer, V. Harrowfield, J., Vicens, J.: Calixarenes 2001. Kluwer Academic, Dordrecht (2001); (e) McKervey, M.A., Arnaud-Neu, F., Schwing-Weill, M.-J. In: Gokel, G., (ed.) Comprehensive Supramolecular Chemistry, vol. 1, pp. 537–603, Pergamon: Oxford, UK (1996); (f) Wieser, C., Dieleman, C.B., Matt, D.: Calixarene and resorcinarene ligands in transition metal chemistry. Coord. Chem. Rev. 165, 93–161 (1997); (g) Ikeda, A., Shinkaï, S.: Novel cavity design using calix[n]arene skeletons: toward molecular recognition and metal binding. Chem. Rev. 97, 1713–1734 (1997); (h) Harvey, P.D.: Wide-rim and outer-face functionalizations of calix[4]arene. Coord. Chem. Rev. 233–234, 289–309 (2002); (i) Sliwa, W.: Calixarene complexes with transition metal ions. J. Incl. Phenom. Macrocyclic Chem. 52, 13–37 (2005).
2. 2. (a) Vicens, J., Bohmer, V.: Calixarenes A Versatile Class of Macrocyclic Compounds. In: Topics in Inclusion Science, Ed: Kluver Academic Press, Dordrecht (1991); (b) Rebek, J.: Host–guest chemistry of calixarene capsules. Chem. Commun. 637–643 (2000); (c) Le Gac, S., Luhmer, M., Reinaud, O., Jabin, I.: Self-assembly via ionic interactions of calix[6]arene-based receptors displaying remarkable host–guest properties toward neutral guests. Tetrahedron, 63 10721–10730 (2007); (d) Zhao, B.-T. Blesa, M.-J. Le Derf, F., Canevet, D., Benhaoua, C., Mazari, M., Allain M., Salle M.: Carboxylic acid derivatives of tetrathiafulvalene: key intermediates for the synthesis of redox-active calixarene-based anion receptors. Tetrahedron, 63, 10768–10777 (2007).
3. 3. (a) Delmau, L.H., Simon, N., Schwing-Weill, M.-J., Arnaud-Neu, F., Dozol, J.-F., Eymard, S., Tournois, B., Böhmer, V., Grüttner, C., Musigmann, C., Tunayar, A.: ‘CMPO-substituted’ calix[4]arenes, extractants with selectivity among trivalent lanthanides and between trivalent actinides and lanthanides. Chem. Commun. 1627–1628 (1998); (b) Barboso, S., Carrera, A.G., Matthews, S.E., Arnaud-Neu, F., Böhmer, V., Dozol, J.-F., Rouquette, H., Schwing-Weill, M.-J.: Calix[4]arenes with CMPO functions at the narrow rim. Synthesis and extraction properties. J. Chem. Soc., Perkin Trans. 2, 719–723 (1999); (c) Matthews, S. E., Saadioui, M., Böhmer, V., Barboso, S., Arnaud-Neu, F., Schwing-Weill, M.-J., Carrera, A. G., Dozol, J.-F.: Conformationally mobile wide rim carbamoylmethylphosphine oxide (CMPO)-calixarenes. J. Prakt. Chem. 341, 264–273 (1999); (d) Arduini, A., Böhmer, V., Delmau, L., Desreux, J.-F., Dozol, J.-F., Garcia Carrera, A.M., Lambert, B., Musigmann, C., Pochini, A., Shivanyuk, A., Ugozzoli, F.: Rigidified calixarenes bearing four carbamoylmethylphosphineoxide or carbamoylmethylphosphoryl functions at the wide rim. Chem. Eur. J. 6, 2135–2142 (2000); (e) Schmidt, C., Saadioui, M., Böhmer, V., Host, V., Spirlet, M.-R., Desreux, J.F., Brisach, F., Arnaud-Neu, F., Dozol, J.-F.: Modification of calix[4]arenes with CMPO-functions at the wide rim. Synthesis, solution behavior, and separation of actinides from lanthanides. Org. Biomol. Chem. 1, 4089–4096 (2003); (f) Motornaya, A., Vatsouro, I., Shokova, E., Hubscher-Bruder, V., Alyapyshev, M., Babain, V., Karavan, M., Arnaud-Neu, F., Böhmer, V., Kovalev, V.: Adamantylcalixarenes with CMPO groups at the wide rim: synthesis and extraction of lanthanides and actinides. Tetrahedron 63, 4748–4755 (2007).
4. 4. F. Neu J.K. Browne D. Byrne D.J. Marrs M.A. McKervey P. O’Hagan M.J. Schwing-Weill A. Walker 1999 Extraction and complexation of alkali, alkaline earth, and f-element cations by calixaryl phosphine oxides Chem. Eur. J. 5 175 186 10.1002/(SICI)1521-3765(19990104)5:1<175::AID-CHEM175>3.0.CO;2-P Arnaud-Neu, F., Browne, J.K., Byrne, D., Marrs, D.J., McKervey, M.A., O’Hagan, P., Schwing-Weill, M.J., Walker, A.: Extraction and complexation of alkali, alkaline earth, and f-element cations by calixaryl phosphine oxides. Chem. Eur. J. 5, 175–186 (1999).
5. 5. Beer, P.D., Brindley, G.D., Fox, O.D., Grieve, A., Ogden, M.I., Szemes, F., Drew, M.G.B.: Acid-amide calixarene ligands for uranyl and lanthanide ions: synthesis, structure, coordination and extraction studies. J. Chem. Soc. Dalton Trans., 3101–3111 (2002).
6. 6. (a) Jurecka, P., Vojtisek, P., Novotny, K., Rohovec, J., Lukes, I.: Synthesis, characterisation and extraction behaviour of calix[4]arene-based phosphonic acids. J. Chem. Soc., Perkin Trans. 2, 1370–1377 (2002); (b) Matulkova, I., Rohovec, J.: Synthesis, characterization and extraction behaviour of calix[4]arene with four propylene phosphonic acid groups on the lower rim. Polyhedron 24, 311–317 (2005).
7. 7. For example (a) Froidevaux, P., Harrowfield, J.M., Sobolev, A.N.: Calixarenes as scaffolds: introduction of tridentate rare earth metal binding units into calix[4]arene. Inorg. Chem. 39, 4678–4687 (2000); (b) Atamas, L., Klimchuk, O., Rudzevich, V., Pirozhenko, V., Kalchenko, V., Smirnov, I., Babain, V., Efremova, T., Varnek, A., Wipff, G., Arnaud-Neu, F., Roch, M., Saadioui, M., Böhmer, V.: New organophosphorus calix[4]arene ionophores for trivalent lanthanide and actinide cations. J. Supramol. Chem. 2, 421–427 (2002); (c) Ziessel, R.F., Charbonnière, L.J., Cesario, M., Prangé, T., Guardigli, M., Roda, A., Van Dorsselaer, A., Nierengarten, H.: p-tert-Butylcalix[4]arene functionalised with bipyridyl carboxylates for lanthanide complexation: Synthesis, photophysical properties, solution and solid state behaviour. Supramol. Chem. 15, 277–289 (2003); (d) Kajiwara, M., Koga, M., Nishida, M., Yoshida, I.: Complex formation of p-nitrocalix[6]arene with rare earth metal ions. Anal. Sci. 22, 457–460 (2006).
8. 8. Martell, A.E., Smith, R.M.: Critical Stability Constant. Plenum, Press New York, vol. 1 (1974).
9. 9. (a) Dutta, S., Kim, S.-K. Patel, D.B., Kim, T.-J., Chang, Y.: Some new DTPA-N,N″-bis(amides) functionalized by alkyl carboxylates: Synthesis, complexation and stability properties. Polyhedron 26, 3799–3809 (2007); (b) Yu, G., Yamashita, M., Aoshima, K., Takahashi, M., Oshikawa, T., Takayanagi, H., Laurent, S., Burtea, C., Vander Elst L., Muller, R.N.: A glycosylated complex of gadolinium, a new potential contrast agent for magnetic resonance angiography? Bioorg. Med. Chem. Lett., 17, 2246–2249, (2007); (c) Roberto, A., Mauro, B., Camilla, C., Giovanni, G., B.; Giovanni, P., Massimo, S.: Novel functionalized pyridine-containing DTPA—like ligand. Synthesis, computational studies and characterization of the corresponding GdIII complex. Org. Biomol. Chem. 5, 2441–2447, (2007); (d) Debouttière, P.-J., Roux, S., Vocanson, F., Billotey, C., Beuf, O., Favre-Réguillon, A., Lin, Y., Pellet-Rostaing, S., Lamartine, R., Perriat, P., Tillement, O.: Design of gold nanoparticles for magnetic resonance imaging. Adv. Funct. Mater. 16, 2330–2339 (2006).
10. 10. I. Bitter A. Grün G. Toth B. Balays L. Toke 1997 Studies on calix(aza)crowns, I. Synthesis, alkylation reactions and comprehensive NMR investigation of capped calix[4]arenes Tetrahedron 53 9799 9812 10.1016/S0040-4020(97)00627-3 1:CAS:528:DyaK2sXkslCitb4%3D Bitter, I., Grün, A., Toth, G., Balays, B., Toke, L.: Studies on calix(aza)crowns, I. Synthesis, alkylation reactions and comprehensive NMR investigation of capped calix[4]arenes. Tetrahedron 53, 9799–9812 (1997).
11. 11. (a) Mortellaro, M.A., Nocera, D.G.: A supramolecular chemosensor for aromatic hydrocarbons. J. Am. Chem. Soc. 118, 7414–7415 (1996); (b) Rudzinski, C.M., Engebretson, D.S., Hartmann, W.K., Nocera, D.G.: Mechanism for the sensitized luminescence of a lanthanide ion macrocycle appended to a cyclodextrin. J. Phys. Chem. A 102, 7442–7446 (1998).
12. 12. F. Szemes D. Hesek Z. Chen S.W. Dent M.G. Drew A.J. Goulden A.R. Grayon A. Grieve J. Mortimer T. Wear J.S. Weightman P.D. Beer 1996 Synthesis and characterization of novel acyclic, macrocyclic, and calix[4]arene ruthenium(II) bipyridyl receptor molecules that recognize and sense anions Inorg. Chem. 35 5868 5879 10.1021/ic960318l 1:CAS:528:DyaK28XlsVWisbk%3D Szemes, F., Hesek, D., Chen, Z., Dent, S.W., Drew, M.G.B., Goulden, A.J., Grayon, A.R., Grieve, A., Mortimer, J., Wear, T., Weightman, J.S., Beer, P.D.: Synthesis and characterization of novel acyclic, macrocyclic, and calix[4]arene ruthenium(II) bipyridyl receptor molecules that recognize and sense anions. Inorg. Chem. 35, 5868–5879 (1996).
13. 13. C. Danila M. Bolte V. Böhmer 2005 1,3-Alternate calix[4]arenes, selectively functionalized by amino groups Org. Biomol. Chem. 3 172 184 10.1039/b414173c 1:CAS:528:DC%2BD2cXhtVylt7vF Danila, C., Bolte, M., Böhmer, V.: 1,3-Alternate calix[4]arenes, selectively functionalized by amino groups. Org. Biomol. Chem. 3, 172–184 (2005).
14. 14. H. Halouani I. Dumazet-Bonnamour M. Perrin R. Lamartine 2004 First synthesis and structure of β-ketoimine calix[4]arenes: Complexation and extraction studies J. Org. Chem. 69 6521 6527 10.1021/jo0495485 1:CAS:528:DC%2BD2cXntFCqtbg%3D Halouani, H., Dumazet-Bonnamour, I., Perrin, M., Lamartine, R.: First synthesis and structure of β-ketoimine calix[4]arenes: Complexation and extraction studies. J. Org. Chem. 69, 6521–6527 (2004).
15. 15. (a) Carvalho, J.F., Kim, S.–H., Chang, C.A.: Synthesis and metal complex selectivity of macrocyclic DTPA and EDTA bis(amide) ligands. Inorg. Chem., 31, 4065–4068 (1992); (b) Fu, Y., Laurent, S., Muller, R.N.: Synthesis of a sialyl lewisX mimetic conjugated with DTPA, potential ligand of new contrast agents for medical imaging. Eur. J. Org. Chem. 23, 3966–3973 (2002).
16. 16. He, W., Liu, F., Mei, Y., Guo, Z., Zhu, L.: Synthesis and electrospray mass spectrometry study of Pd(II) complexes of low-rim amino acid substituted calix[4]arenes. New J. Chem. 25, 1330–1336, (2001).
17. 17. C. Jaime J. Mendoza P. Prados P.M. Nieto C. Sanchez 1991 13C NMR chemical shifts. A single rule to determine the conformation of calix[4]arenas J. Org. Chem. 56 3372 3376 10.1021/jo00010a036 1:CAS:528:DyaK3MXisVKksro%3D Jaime, C., Mendoza, J., Prados, P., Nieto, P.M., Sanchez, C.: 13C NMR chemical shifts. A single rule to determine the conformation of calix[4]arenas. J. Org. Chem. 56, 3372–3376 (1991).
18. 18. P.D. Beer D. Hesek J.E. Kingston D.K. Smith S.E. Stokes 1995 Anion recognition by redox-responsive ditopic bis-cobaltocenium receptor molecules including a novel calix[4]arene derivative that binds a dicarboxylate dianion Organometallics 14 3288 3295 10.1021/om00007a032 1:CAS:528:DyaK2MXmsVeisrk%3D Beer, P.D., Hesek, D., Kingston, J.E., Smith, D.K., Stokes, S.E.: Anion recognition by redox-responsive ditopic bis-cobaltocenium receptor molecules including a novel calix[4]arene derivative that binds a dicarboxylate dianion. Organometallics 14, 3288–3295 (1995).
19. 19. E. Brunet O. Juanes R. Sedano J.C. Rodriguez-Ubis 2002 Synthesis of novel macrocyclic lanthanide chelates derived from bis-pyrazolylpyridine Org. Lett. 4 213 216 10.1021/ol0169527 1:CAS:528:DC%2BD3MXpt1Cnt7k%3D Brunet, E., Juanes, O., Sedano, R., Rodriguez-Ubis, J.C.: Synthesis of novel macrocyclic lanthanide chelates derived from bis-pyrazolylpyridine. Org. Lett. 4, 213–216 (2002).
20. 20. S.J. Franklin K.N. Raymond 1994 Solution structure and dynamics of lanthanide complexes of the macrocyclic polyamino carboxylate DTPA-dien. NMR study and crystal structures of the lanthanum(III) and europium(III) complexes Inorg. Chem. 33 5794 5804 10.1021/ic00103a029 1:CAS:528:DyaK2cXntFCnurk%3D Franklin, S.J., Raymond, K.N.: Solution structure and dynamics of lanthanide complexes of the macrocyclic polyamino carboxylate DTPA-dien. NMR study and crystal structures of the lanthanum(III) and europium(III) complexes. Inorg. Chem. 33, 5794–5804 (1994).