메뉴 건너뛰기




Volumn 68, Issue 3-4, 2010, Pages 387-398

Structures of urea/thiourea 1,3-disubstituted thia[4]calixarenes and corresponding monofunctional receptors and their anion recognition properties

Author keywords

Anion recognition; Structure; Thiacalixarene; Thiourea; Urea

Indexed keywords


EID: 78649319612     PISSN: 09230750     EISSN: None     Source Type: Journal    
DOI: 10.1007/s10847-010-9798-0     Document Type: Article
Times cited : (18)

References (46)
  • 1
    • 38149103276 scopus 로고    scopus 로고
    • Anion receptors based on organic frameworks: highlights from 2005 and 2006
    • Reviews
    • Gale, P. A., García-Garrido, S. E., Garric, J.: Anion receptors based on organic frameworks: highlights from 2005 and 2006. Chem. Soc. Rev. 37, 151-190 (2008). Reviews.
    • (2008) Chem. Soc. Rev. , vol.37 , pp. 151-190
    • Gale, P.A.1    García-Garrido, S.E.2    Garric, J.3
  • 2
    • 45249097171 scopus 로고    scopus 로고
    • An introduction to anion receptors based on organic frameworks
    • Bates, G. W., Gale, P. A.: An introduction to anion receptors based on organic frameworks. Struct. Bond 129, 1-44 (2008).
    • (2008) Struct. Bond , vol.129 , pp. 1-44
    • Bates, G.W.1    Gale, P.A.2
  • 3
    • 33745215609 scopus 로고    scopus 로고
    • A modular approach to anion binding podands: adaptability in design and synthesis leads to adaptability in properties
    • Steed, J. W.: A modular approach to anion binding podands: adaptability in design and synthesis leads to adaptability in properties. Chem. Commun. 2637-2649 (2006).
    • (2006) Chem. Commun , pp. 2637-2649
    • Steed, J.W.1
  • 7
    • 38749134838 scopus 로고    scopus 로고
    • Effect of spacer geometry on oxoanion binding by bis- and tetrakis-thiourea hosts
    • Leung, A. N., Degenhardt, D. A., Bühlmann, P.: Effect of spacer geometry on oxoanion binding by bis- and tetrakis-thiourea hosts. Tetrahedron 64, 2530-2536 (2008).
    • (2008) Tetrahedron , vol.64 , pp. 2530-2536
    • Leung, A.N.1    Degenhardt, D.A.2    Bühlmann, P.3
  • 8
    • 34247585495 scopus 로고    scopus 로고
    • Steric and electronic factors influencing recognition by a simple, charge neutral norbornene based anion receptor
    • Lowe, A. J., Dyson, G. A., Pfeffer, F. M.: Steric and electronic factors influencing recognition by a simple, charge neutral norbornene based anion receptor. Org. Biomol. Chem. 5, 1343-1346 (2007).
    • (2007) Org. Biomol. Chem. , vol.5 , pp. 1343-1346
    • Lowe, A.J.1    Dyson, G.A.2    Pfeffer, F.M.3
  • 9
    • 33750601661 scopus 로고    scopus 로고
    • Pyridyl thioureas as switchable anion receptors
    • Rashdan, S., Light, M. E., Kilburn, J. D.: Pyridyl thioureas as switchable anion receptors. Chem. Commun. 4578-4580 (2006).
    • (2006) Chem. Commun , pp. 4578-4580
    • Rashdan, S.1    Light, M.E.2    Kilburn, J.D.3
  • 11
    • 33644532827 scopus 로고    scopus 로고
    • A conformationally flexible, urea-based tripodal anion receptor: solid-state, solution, and theoretical studies
    • Turner, D. R., Paterson, M. J., Steed, J. W.: A conformationally flexible, urea-based tripodal anion receptor: solid-state, solution, and theoretical studies. J. Org. Chem. 71, 1598-1608 (2006).
    • (2006) J. Org. Chem. , vol.71 , pp. 1598-1608
    • Turner, D.R.1    Paterson, M.J.2    Steed, J.W.3
  • 12
    • 33751158907 scopus 로고
    • Urea-derivatized p-tert-butylcalix[4]arenes: neutral ligands for selective anion complexation
    • Scheerder, J., Fochi, M., Engbersen, J. F. J., Reinhoudt, D. N.: Urea-derivatized p-tert-butylcalix[4]arenes: neutral ligands for selective anion complexation. J. Org. Chem. 59, 7815-7820 (1994).
    • (1994) J. Org. Chem. , vol.59 , pp. 7815-7820
    • Scheerder, J.1    Fochi, M.2    Engbersen, J.F.J.3    Reinhoudt, D.N.4
  • 13
    • 33746144048 scopus 로고    scopus 로고
    • Anion receptors based on calixarenes
    • Lhoták, P.: Anion receptors based on calixarenes. Top. Curr. Chem. 255, 65 (2005).
    • (2005) Top. Curr. Chem. , vol.255 , pp. 65
    • Lhoták, P.1
  • 14
    • 33745700242 scopus 로고    scopus 로고
    • Chloride selective calix[4]arene optical sensor combining urea functionality with pyrene excimer transduction
    • Schazmann, B., Alhashimy, N., Diamond, D. J.: Chloride selective calix[4]arene optical sensor combining urea functionality with pyrene excimer transduction. Am. Chem. Soc. 128, 8607-8614 (2006).
    • (2006) Am. Chem. Soc. , vol.128 , pp. 8607-8614
    • Schazmann, B.1    Alhashimy, N.2    Diamond, D.J.3
  • 15
    • 17644365726 scopus 로고    scopus 로고
    • Stepwise and dramatic enhancement of anion recognition with a triple-site receptor based on the calix[4]arene framework using two different cationic effectors
    • Nabeshima, T., Saiki, T., Iwabuchi, J., Akine, S. J.: Stepwise and dramatic enhancement of anion recognition with a triple-site receptor based on the calix[4]arene framework using two different cationic effectors. Am. Chem. Soc. 127, 5507-5511 (2005).
    • (2005) Am. Chem. Soc. , vol.127 , pp. 5507-5511
    • Nabeshima, T.1    Saiki, T.2    Iwabuchi, J.3    Akine, S.J.4
  • 16
  • 17
    • 61849099478 scopus 로고    scopus 로고
    • Anion recognition by diureido-calix[4]arenes in the 1,3-alternate conformation
    • Curinova, P., Stibor, I., Budka, J., Sykora, J., Lang, K., Lhotak, P.: Anion recognition by diureido-calix[4]arenes in the 1, 3-alternate conformation. New J. Chem. 33, 612-619 (2009).
    • (2009) New J. Chem. , vol.33 , pp. 612-619
    • Curinova, P.1    Stibor, I.2    Budka, J.3    Sykora, J.4    Lang, K.5    Lhotak, P.6
  • 18
    • 0345850147 scopus 로고    scopus 로고
    • Synthesis and anion-selective complexation of cyclophane-based cyclic thioureas
    • Sasaki, S., Mizuno, M., Naemura, K., Tobe, Y. J.: Synthesis and anion-selective complexation of cyclophane-based cyclic thioureas. Org. Chem. 65, 275-283 (2000).
    • (2000) Org. Chem. , vol.65 , pp. 275-283
    • Sasaki, S.1    Mizuno, M.2    Naemura, K.3    Tobe, Y.J.4
  • 19
    • 0141433488 scopus 로고    scopus 로고
    • Synthesis and dual binding character of novel macrocyclic thiourea derivatives
    • Okumura, Y., Murakami, S., Maeda, H., Matsumura, N., Mizuno, K.: Synthesis and dual binding character of novel macrocyclic thiourea derivatives. Tetrahedron Lett. 44, 8183-8185 (2003).
    • (2003) Tetrahedron Lett. , vol.44 , pp. 8183-8185
    • Okumura, Y.1    Murakami, S.2    Maeda, H.3    Matsumura, N.4    Mizuno, K.5
  • 21
    • 29744439744 scopus 로고    scopus 로고
    • Anion receptors based on ureido-thiacalix[4]arenes
    • Lhoták, P., Svoboda, J., Stibor, I.: Anion receptors based on ureido-thiacalix[4]arenes. Tetrahedron 62, 1253-1257 (2006).
    • (2006) Tetrahedron , vol.62 , pp. 1253-1257
    • Lhoták, P.1    Svoboda, J.2    Stibor, I.3
  • 22
    • 8644273283 scopus 로고    scopus 로고
    • Novel anion receptors based on thiacalix[4]arene derivatives
    • Zlatušková, P., Stibor, I., Tkadlecová, M., Lhoták, P.: Novel anion receptors based on thiacalix[4]arene derivatives. Tetrahedron 60, 11383-11390 (2004).
    • (2004) Tetrahedron , vol.60 , pp. 11383-11390
    • Zlatušková, P.1    Stibor, I.2    Tkadlecová, M.3    Lhoták, P.4
  • 23
    • 50849107650 scopus 로고    scopus 로고
    • Anion receptors based on ureido-substituted thiacalix[4]arenes and calix[4]arenes
    • Kroupa, J., Stibor, I., Pojarova, M., Tkadlecova, M., Lhotak, P.: Anion receptors based on ureido-substituted thiacalix[4]arenes and calix[4]arenes. Tetrahedron 64, 10075-10079 (2008).
    • (2008) Tetrahedron , vol.64 , pp. 10075-10079
    • Kroupa, J.1    Stibor, I.2    Pojarova, M.3    Tkadlecova, M.4    Lhotak, P.5
  • 25
    • 4444241208 scopus 로고    scopus 로고
    • Chemistry of thiacalixarenes
    • Lhotak, P.: Chemistry of thiacalixarenes. Eur. J. Org. Chem. 1675-1692 (2004).
    • (2004) Eur. J. Org. Chem , pp. 1675-1692
    • Lhotak, P.1
  • 26
    • 60849123938 scopus 로고    scopus 로고
    • Non-covalent strategy for activating separation and detection functionality by use of the multifunctional host molecule thiacalixarene
    • Iki, N.: Non-covalent strategy for activating separation and detection functionality by use of the multifunctional host molecule thiacalixarene. J. Incl. Phenom. Macrocycl. Chem. 64, 1-13 (2009).
    • (2009) J. Incl. Phenom. Macrocycl. Chem. , vol.64 , pp. 1-13
    • Iki, N.1
  • 27
    • 33745019621 scopus 로고    scopus 로고
    • Synthesis and inclusion properties of a novel thiacalix[4]arene-based hard-soft receptor with 1,3-alternate conformation
    • Yamato, T., Perez-Casas, C., Elsegood, M. R. J., Dale, S. H., Redshaw, C.: Synthesis and inclusion properties of a novel thiacalix[4]arene-based hard-soft receptor with 1, 3-alternate conformation. J. Incl. Phenom. Macrocycl. Chem. 55, 31-36 (2006).
    • (2006) J. Incl. Phenom. Macrocycl. Chem. , vol.55 , pp. 31-36
    • Yamato, T.1    Perez-Casas, C.2    Elsegood, M.R.J.3    Dale, S.H.4    Redshaw, C.5
  • 28
    • 77952288215 scopus 로고    scopus 로고
    • Syntheses, reactions and crystal structures of 1, 3-alternate p-tert-butylthiacalix[4]arene esters and amides
    • doi: 10. 1007/s10847-009-9652-4
    • Liu, L., Huang, K., Yan, C. G.: Syntheses, reactions and crystal structures of 1, 3-alternate p-tert-butylthiacalix[4]arene esters and amides. J. Incl. Phenom. Macrocycl. Chem. (2009) doi: 10. 1007/s10847-009-9652-4.
    • (2009) J. Incl. Phenom. Macrocycl. Chem
    • Liu, L.1    Huang, K.2    Yan, C.G.3
  • 29
    • 38149032895 scopus 로고    scopus 로고
    • Selectivity in supramolecular host-guest complexes
    • Schneider, H.-J., Yatsimirsky, A. K.: Selectivity in supramolecular host-guest complexes. Chem. Soc. Rev. 37, 263-277 (2008).
    • (2008) Chem. Soc. Rev. , vol.37 , pp. 263-277
    • Schneider, H.-J.1    Yatsimirsky, A.K.2
  • 30
    • 0030908399 scopus 로고    scopus 로고
    • Facile synthesis of p-tert-butylthiacalix[4]arene by the reaction of p-tert-butylphenol with elemental sulfur in the presence of a base
    • Kumagi, H., Hasegawa, M., Miyanari, S., Sugawa, Y., Sato, Y., Hori, T., Udea, S., Kamiyama, H., Miyano, S.: Facile synthesis of p-tert-butylthiacalix[4]arene by the reaction of p-tert-butylphenol with elemental sulfur in the presence of a base. Tetrahedron Lett. 38, 3971-3972 (1997).
    • (1997) Tetrahedron Lett. , vol.38 , pp. 3971-3972
    • Kumagi, H.1    Hasegawa, M.2    Miyanari, S.3    Sugawa, Y.4    Sato, Y.5    Hori, T.6    Udea, S.7    Kamiyama, H.8    Miyano, S.9
  • 31
    • 28944440724 scopus 로고    scopus 로고
    • Regioselective synthesis of distal-bisalkoxytetrathiacalix[4]arenes by a protection-deprotection method using benzyl groups
    • Pérez-Casas, C., Yamamoto, H., Yamato, T.: Regioselective synthesis of distal-bisalkoxytetrathiacalix[4]arenes by a protection-deprotection method using benzyl groups. J. Chem. Res. 694-696 (2005).
    • (2005) J. Chem. Res , pp. 694-696
    • Pérez-Casas, C.1    Yamamoto, H.2    Yamato, T.3
  • 32
    • 38049024696 scopus 로고    scopus 로고
    • Design, synthesis and recognition properties of urea-type anion receptors in low polar media
    • Pescatori, L., Arduini, A., Pochini, A., Ugozzoli, F., Secchi, A.: Design, synthesis and recognition properties of urea-type anion receptors in low polar media. Eur. J. Org. Chem. 109-120 (2008).
    • (2008) Eur. J. Org. Chem , pp. 109-120
    • Pescatori, L.1    Arduini, A.2    Pochini, A.3    Ugozzoli, F.4    Secchi, A.5
  • 33
    • 52449122329 scopus 로고    scopus 로고
    • Calix[6]tris(thio)ureas: heteroditopic receptors for the cooperative binding of organic ion pairs
    • Hamon, M., Ménand, M., Le Gac, S., Luhmer, M., Dalla, V., Jabin, I. J.: Calix[6]tris(thio)ureas: heteroditopic receptors for the cooperative binding of organic ion pairs. Org. Chem. 73, 7067-7071 (2008).
    • (2008) Org. Chem. , vol.73 , pp. 7067-7071
    • Hamon, M.1    Ménand, M.2    Le Gac, S.3    Luhmer, M.4    Dalla, V.5    Jabin, I.J.6
  • 34
    • 41849114198 scopus 로고    scopus 로고
    • Detailing hydrogen bonding and deprotonation equilibria between anions and urea/thiourea derivatives
    • Pérez-Casas, C., Yatsimirsky, A. K.: Detailing hydrogen bonding and deprotonation equilibria between anions and urea/thiourea derivatives. J. Org. Chem. 73, 2275-2284 (2008).
    • (2008) J. Org. Chem. , vol.73 , pp. 2275-2284
    • Pérez-Casas, C.1    Yatsimirsky, A.K.2
  • 38
    • 22144435917 scopus 로고    scopus 로고
    • Why, on interaction of urea-based receptors with fluoride, beautiful colors develop
    • Esteban-Gómez, D., Fabbrizzi, L., Licchelli, M.: Why, on interaction of urea-based receptors with fluoride, beautiful colors develop. J. Org. Chem. 70, 5717-5720 (2005).
    • (2005) J. Org. Chem. , vol.70 , pp. 5717-5720
    • Esteban-Gómez, D.1    Fabbrizzi, L.2    Licchelli, M.3
  • 39
    • 0344887064 scopus 로고
    • Equilibrium acidities in dimethyl sulfoxide solution
    • Bordwell, F. G.: Equilibrium acidities in dimethyl sulfoxide solution. Acc. Chem. Res. 21, 456-463 (1988).
    • (1988) Acc. Chem. Res. , vol.21 , pp. 456-463
    • Bordwell, F.G.1
  • 41
    • 4744356299 scopus 로고    scopus 로고
    • Crystal synthesis of hybrid organometallic-inorganic hydrogen bonded salts of acid oxoanions
    • Braga, D., Curzi, M., Maini, L., Polito, M., Grepioni, F.: Crystal synthesis of hybrid organometallic-inorganic hydrogen bonded salts of acid oxoanions. Dalton Trans. 2432-2437 (2004).
    • (2004) Dalton Trans , pp. 2432-2437
    • Braga, D.1    Curzi, M.2    Maini, L.3    Polito, M.4    Grepioni, F.5
  • 42
    • 46749146511 scopus 로고    scopus 로고
    • New branched macrocyclic ligand and its side-arm, two urea-based receptors for anions: synthesis, binding studies and crystal structure
    • Formica, M., Fusi, V., Macedi, E., Paoli, P., Piersanti, G., Rossi, P., Zappiac, G., Orlando, P.: New branched macrocyclic ligand and its side-arm, two urea-based receptors for anions: synthesis, binding studies and crystal structure. New J. Chem. 32, 1204-1214 (2008).
    • (2008) New J. Chem. , vol.32 , pp. 1204-1214
    • Formica, M.1    Fusi, V.2    Macedi, E.3    Paoli, P.4    Piersanti, G.5    Rossi, P.6    Zappiac, G.7    Orlando, P.8
  • 44
    • 11144331697 scopus 로고    scopus 로고
    • Bruker Analytical X-ray Systems
    • Bruker Analytical X-ray Systems, SAINT + NT, Versions 6. 01 and 6. 04, (1999) and (2001).
    • (1999) SAINT + NT, Versions 6.01 and 6.04
  • 46
    • 78649325313 scopus 로고    scopus 로고
    • Bruker Analytical X-ray Systems, SHELXTL-NT Versions 5. 10 and 6. 10, (1999) and (2000).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.