A dipyrenyl calixazacrown chemosensor for Mg2+

Tetrahedron

Volumn 65, Issue 14, 2009, Pages 2818-2823

  Hamdi, Abdelwaheb ^a   Kim, Sang Hoon ^b   Abidi, Rym ^a   Thuéry, Pierre ^c   Kim, Jong Seung ^b   Vicens, Jacques ^d  

^a University of Carthage   (Tunisia)

^b Korea University   (South Korea)

^c CNRS UMR 3299   (France)

^d CNRS   (France)

Author keywords

Calixarenes; Complexation; Detection; Excimer; Fluorescence; Magnesium

Indexed keywords

AMIDE; CALIX[4]TETRAAZA CROWN 6; HETEROCYCLIC COMPOUND; MAGNESIUM; MONOMER; PYRENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHELATION; CONFORMATIONAL TRANSITION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 61349202333     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.01.079     Document Type: Article

References (68)

1. Czarnik A.W. Chem. Biol. 2 (1995) 423
2. In: Desvergnes J.P., and Czarnik A.W. (Eds). Chemosensors for Ion and Molecule Recognition. NATO ASI Series (1997), Kluwer Academic, Dordrecht
3. de Silva A.P., Gunaratne H.Q.N., Gunnlaugsson T., Huxley A.J.M., McCoy C.P., Rademacher J.T., and Rice T.E. Chem. Rev. 97 (1997) 1515
4. Schmidtchen F.P., and Berger M. Chem. Rev. 97 (1997) 1609
5. Gale P.A. Coord. Chem. Rev. 199 (2000) 181
6. Fabrizzi, L. has edited a special issue on 'Luminescent Sensors':. Coord. Chem. Rev. 205 (2000) 1
7. Bren V.A. Russ. Chem. Rev. 70 (2001) 1017
8. Gale P.A. Coord. Chem. Rev. 213 (2001) 79
9. Valeur B. Molecular Fluorescence (2002), Wiley-VCH, Weinheim
10. Diamond D., and Nolan K. Anal. Chem. 73 (2001) 22A
11. Beer P.D., and Gale P.A. Angew. Chem., Int. Ed. 40 (2001) 486
12. Ludwig R., and Dzung N.T.K. Sensors 2 (2002) 397
13. Martinez-Manez R., and Sancenon F. Chem. Rev. 103 (2003) 4419
14. Callan J.F., de Silva A.P., and Magri D.C. Tetrahedron 61 (2005) 8551
15. Dallali N., Darabi A., and Agrawal Y.K. Rev. Anal. Chem. 24 (2005) 263
16. Amendola V., Fabbrizzi I., Forti F., Pallavicini P., Poggi A., Sacchi D., and Tagleitti A. Coord. Chem. Rev. 250 (2006) 273
17. Kungwandi B., Nuriman, Verboom W., and Reinhoudt D.N. Sensors 6 (2006) 978
18. Mancin F., Rampazzo E., Tecilla P., and Tonallato U. Chem.-Eur. J. 12 (2006) 1844
19. Valeur B., and Leray I. Inorg. Chim. Acta 360 (2007) 765
20. Löhr H.-G., and Vögtle F. Acc. Chem. Res. 18 (1985) 65
21. Yang X.-F., Guo X.-Q., and Zhao Y.-B. Talanta 57 (2002) 883
22. Zhu L., and Anslyn E.V. Angew. Chem., Int. Ed. 45 (2006) 1190
23. Anslyn E.V. J. Org. Chem. 72 (2007) 687
24. Bell T.W., and Hext N.M. Chem. Soc. Rev. 33 (2004) 589
25. Nohta H., Satozono H., Koiso K., Yoshida H., Ishida J., and Yamaguchi M. Anal. Chem. 72 (2000) 4199
26. Okamoto A., Ichiba T., and Saito I. J. Am. Chem. Soc. 126 (2004) 8364
27. Birks J.B. Photophysics of Aromatic Molecules (1970), Wiley-Interscience, London
28. Winnik F.M. Chem. Rev. 93 (1993) 587
29. Kim S.K., Bok J.H., Bartsch R.A., Lee J.Y., and Kim J.S. Org. Lett. 7 (2005) 4839
30. Kim S.K., Lee S.H., Lee J.Y., Lee J.Y., Bartsch R.A., and Kim J.S. J. Am. Chem. Soc. 126 (2004) 16499
31. Kim H.J., Hong J., Hong A., Ham S., Lee J.H., and Kim J.S. Org. Lett. 10 (2008) 1963
32. Choi J.K., Lee A., Kim S., Ham S., No K., and Kim J.S. Org. Lett. 8 (2006) 1601
33. Choi J.K., Kim S.H., Yoon J., Lee K.H., and Kim J.S. J. Org. Chem. 71 (2006) 8015
34. Muthukrishnan R., and Gutsche C.D. J. Org. Chem. 44 (1979) 3962
35. Gutsche C.D., Dhawan B., No K.H., and Muthukrishnan R. J. Am. Chem. Soc. 103 (1981) 3782
36. Gutsche C.D. Calixarenes (1989), The Royal Society of Chemistry, Cambridge
37. Gutsche C.D. Calixarenes Revisited (1998), The Royal Society of Chemistry, Cambridge
38. In: Böhmer V., and Vicens J. (Eds). Calixarenes: A Versatile Class of Macrocyclic Compounds (1991), Kluwer Academic, Dordrecht, The Netherlands
39. In: Asfari Z., Böhmer V., Harrowfield J., and Vicens J. (Eds). Calixarenes 2001 (2001), Kluwer Academic, Dordrecht, The Netherlands
40. In: Asfari Z., Harrowfield J., and Vicens J. (Eds). Calixarenes 50th Anniversary: Commemorative Volume (1994), Kluwer Academic, Dordrecht, The Netherlands
41. In: Harrowfield J., and Vicens J. (Eds). Calixarenes in the Nanoworld (2007), Springer, Dordrecht, The Netherlands
42. See the following reviews:
43. Valeur B., and Leray I. Coord. Chem. Rev. 205 (2000) 3
44. Kim S.H., Kim H.J., Yoon J., and Kim J.S. In: Harrowfield J., and Vicens J. (Eds). Calixarenes in The Nanoworld (2007), Springer, Dordrecht, The Netherlands Chapter 15
45. Kim J.S., and Quang D.T. Chem. Rev. 107 (2007) 3780
46. Broan C.J. Chem. Commun. (1996) 699
47. Park S.Y., Yoon J.H., Hong C.S., Souane R., Kim J.S., Matthews S.E., and Vicens J. J. Org. Chem. 73 (2008) 8212
48. Lee J.Y., Kim S.K., Jung J.H., and Kim J.S. J. Org. Chem. 70 (2005) 1463
49. Lee S.H., Kim S.H., Kim S.K., Jung J.H., and Kim J.S. J. Org. Chem. 70 (2005) 9288
50. 2+ see:
51. Song K.C., Choi M.G., Ryu D.H., Kim K.N., and Chang S.-K. Tetrahedron Lett. 48 (2007) 5397
52. Liu Y., Zhang H.-Y., Yang L.-X., and Jiang W. Org. Lett. 10 (2008) 2873
53. Arunkumar E., Chithra P., and Ayyappanpillai A. J. Am. Chem. Soc. 126 (2004) 6590
54. Farrugia G., Iotti S., Prodi L., Montalti M., Zaccheroni N., Savage P.B., Trapani V., Sale P., and Wolf F.I. J. Am. Chem. Soc. 128 (2006) 344
55. Singh N., Kaur N., Mulrooney R.C., and Callan J.F. Tetrahedron Lett. 49 (2008) 6690
56. Taziaux D., Soumillon J.-Ph., and Jiwan J.-L. J. Photochem. Photobiol., A 162 (2004) 599
57. Prodi L., Bolletta F., Montalti M., Zaccheroni N., Savage B., Bradshaw J.S., and Izatt R.M. Tetrahedron Lett. 39 (1998) 5451
58. Shin E.J. Chem. Lett. (2002) 686
59. Suzuki Y., Komatsu H., Ikeda T., Saito N., Araki S., Citterio D., Hisamoto H., Kitamura Y., Kubota T., Nakagawa J., Oka K., and Suzuki K. Anal. Chem. 74 (2002) 1423
60. Mashraqui S.H., Bhasikuttan S., Bhasikuttan A.C., Kapoor S., and Sapre A.V. Sens. Actuators, B 122 (2007) 347
61. Oueslati I. Tetrahedron 63 (2007) 10840
62. Unob F., Asfari Z., and Vicens J. Tetrahedron Lett. 39 (1998) 2951
63. Oueslati I., Abidi R., Amri H., Thuéry P., Nierlich M., Asfari Z., Harrowfield J., and Vicens J. Tetrahedron Lett. 41 (2000) 8439
64. Van der Veen N.J., Flink S., Deiji M.A., Egberink R.J., van Veggel F.C.J., and Reinhoudt D.N. J. Am. Chem. Soc. 122 (2000) 6112
65. 2+ chelation has been shown by the determination of X-ray structure of a mononuclear calixazacrown-magnesium complex:. Oueslati I., Abidi R., Thuéry P., and Vicens J. J. Inclusion Phenom. Macocyclic Chem. 47 (2003) 173
66. Hooft R.W.W. COLLECT (1998), Nonius BV, Delft, The Netherlands
67. Otwinowski Z., and Minor W. Methods Enzymol. 276 (1997) 307
68. Sheldrick G.M. Acta Crystallogr., Sect. A 64 (2008) 112