A 'clicked' macrocyclic probe incorporating Binol as the signalling unit for the chiroptical sensing of anions

Tetrahedron

Volumn 68, Issue 38, 2012, Pages 7861-7866

  Caricato, Marco ^a   Olmo, Alessandro ^a   Gargiulli, Claudia ^b   Gattuso, Giuseppe ^b   Pasini, Dario ^a  

^a UNIVERSITY OF PAVIA   (Italy)

^b UNIVERSITY OF MESSINA   (Italy)

Author keywords

Anion binding; Circular dichroism; Click chemistry; Macrocycles; Sensors

Indexed keywords

2,2' DIHYDROXY 1,1' BINAPHTHYL; ANION; CARBOXYLIC ACID; CHLOROFORM; HALIDE; HYDROGEN; MACROCYCLIC COMPOUND;

ARTICLE; CHEMICAL BINDING; CONTROLLED STUDY; CYCLIZATION; HYDROGEN BOND; MOLECULAR PROBE; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; SENSOR; SIGNAL TRANSDUCTION; SYNTHESIS;

EID: 84864589648     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2012.07.038     Document Type: Article

References (43)

1. A.P. de Silva, H.Q.N. Gunaratne, T. Gunnlaugsson, A.J.M. Huxley, C.P. McCoy, J.T. Rademacher, and T.E. Rice Chem. Rev. 97 1997 1515 1566
2. N. Berova, L. Di Bari, and G. Pescitelli Chem. Soc. Rev. 36 2007 914 931
3. G.A. Hembury, V.V. Borovkov, and Y. Inoue Chem. Rev. 108 2008 1 73
4. J.W. Canary, S. Mortezaei, and J. Liang Coord. Chem. Rev. 254 2010 2249 2266 See also
5. A. Moletti, C. Coluccini, D. Pasini, and A. Taglietti Dalton Trans. 16 2007 1588 1592
6. D.P. Iwaniuk, and C. Wolf J. Am. Chem. Soc. 133 2011 2414 2417
7. W.-S. Li, D.J. Jiang, Y. Suna, and T. Aida J. Am. Chem. Soc. 127 2005 7700 7702
8. J. Aimi, K. Oya, A. Tsuda, and T. Aida Angew. Chem., Int. Ed. 46 2007 2031 2035
9. G. Fukuhara, and Y. Inoue Chem. - Eur. J. 16 2010 7859 7864
10. G. Fukuhara, and Y. Inoue J. Am. Chem. Soc. 133 2011 768 770
11. A. D'Urso, A. Mammana, M. Balaz, A. Holmes, N. Berova, R. Lauceri, and R. Purrello J. Am. Chem. Soc. 131 2009 2046 2047
12. T. Kurtan, N. Nesnas, Y.-Q. Li, X. Huang, K. Nakanishi, and N. Berova J. Am. Chem. Soc. 123 2001 5962 5973
13. Y.R. Hua, and A.H. Flood Chem. Soc. Rev. 39 2010 1262 1271 For foldamers CD responsive to anions, see
14. R.M. Meudtner, and S. Hecht Angew. Chem., Int. Ed. 47 2008 4926 4930
15. J.-m. Suk, V.R. Naidu, X. Liu, M.S. Lah, and K.-S. Jeong J. Am. Chem. Soc. 133 2011 13938 13941
16. L. Pu Chem. Rev. 98 1998 2405 2494
17. J.M. Brunel Chem. Rev. 105 2005 857 898 For selected recent examples, see
18. B. Olenyuk, J.A. Whiteford, and P.J. Stang J. Am. Chem. Soc. 118 1996 8221 8230
19. Y. Zhu, N. Gergel, N. Majumdar, L.R. Harriott, J.C. Bean, and L. Pu Org. Lett. 8 2006 355 358
20. P. Yan, A.C. Millard, M. Wei, and L.M. Loew J. Am. Chem. Soc. 128 2006 11030 11031
21. L. Ma, D.J. Mihalcik, and W. Lin J. Am. Chem. Soc. 131 2009 4610 4612
22. D. Cornelis, E. Franz, I. Asselberghs, K. Clays, T. Verbiest, and G. Koeckelberghs J. Am. Chem. Soc. 133 2011 1317 1327
23. C. Coluccini, A. Castelluccio, and D. Pasini J. Org. Chem. 73 2008 4237 4240
24. S. Colombo, C. Coluccini, M. Caricato, C. Gargiulli, G. Gattuso, and D. Pasini Tetrahedron 66 2010 4206 4211
25. C. Coluccini, A. Mazzanti, and D. Pasini Org. Biomol. Chem. 8 2010 1807 1815
26. C. Coluccini, D. Dondi, M. Caricato, A. Taglietti, M. Boiocchi, and D. Pasini Org. Biomol. Chem. 8 2010 1640 1649
27. A.S. Droz, U. Neidlein, S. Anderson, P. Seiler, and F. Diederich Helv. Chim. Acta 84 2001 2243 2289
28. T. Kawase, T. Nakamura, K. Utsumi, K. Matsumoto, H. Kurata, and M. Oda Chem. - Asian J. 3 2008 573 577
29. D.J. Cram Angew. Chem., Int. Ed. Engl. 27 1988 1009 1020
30. M. Caricato, C. Coluccini, D. Dondi, D.A. Vander Griend, and D. Pasini Org. Biomol. Chem. 8 2010 3272 3280
31. C. Rosini, S. Superchi, H.W.I. Peerlings, and E.W. Meijer Eur. J. Org. Chem. 2000 61 71
32. V.V. Rostovtsev, L.G. Green, V.V. Fokin, and K.B. Sharpless Angew. Chem., Int. Ed. 41 2002 2596 2599
33. Y. Li, and A.H. Flood Angew. Chem., Int. Ed. 47 2008 2649 2652 This methodology promotes the formation of a copper-acetylide complex, which then undergoes stepwise click reactions, to afford macrocyclic ring closure and product formation
34. W. Zhang, and J.S. Moore Angew. Chem., Int. Ed. 45 2006 4416 4439
35. Such small changes in chemical shift upon binding have been previously and extensively used for the determination of association constants. For a recent example, see: M. Cametti, K. Raatikainen, P. Metrangolo, T. Pilati, G. Terraneo, and G. Resnati Org. Biomol. Chem. 10 2012 1329 1333
36. Attempts to fit the CD binding isotherms with the equation for a 1:1 binding (see: G. Garlaschelli, I. Messina, D. Pasini, and P.P. Righetti Eur. J. Org. Chem. 2002 3385 3392 were unsuccessful
37. R.E. Dawson, A. Hennig, D.P. Weimann, D. Emery, S. Gabutti, J. Montenegro, V. Ravikumar, M. Mayor, J. Mareda, C.A. Schalley, and S. Matile Nat. Chem. 2 2010 533 538 and references therein
38. H.T. Stock, and R.M. Kellogg J. Org. Chem. 61 1996 3093 3105
39. R. Mornet, N.J. Leonard, J.B. Theiler, and M. Doree J. Chem. Soc., Perkin Trans. 1 1984 879 885
40. P.S. Branco, A.M.M. Antunes, M.M. Marques, M.P. Chiarelli, A.M. Lobo, and S. Prabhakar Chem. Res. Toxicol. 12 1999 1223 1233
41. R.M. Meudtner, M. Ostermeier, R. Goddard, C. Limberg, and S. Hecht Chem. - Eur. J. 13 2007 9834 9840
42. M.J. Hynes J. Chem. Soc., Dalton Trans. 1993 311 312
43. Spartan'10, Wavefunction, Inc., Irvine, CA. See: Y. Shao, L.F. Molnar, Y. Jung, J. Kussmann, C. Ochsenfeld, S.T. Brown, A.T.B. Gilbert, L.V. Slipchenko, S.V. Levchenko, D.P. O'Neill, R.A. DiStasio Jr., R.C. Lochan, T. Wang, G.J.O. Beran, N.A. Besley, J.M. Herbert, C.Y. Lin, T. Van Voorhis, S.H. Chien, A. Sodt, R.P. Steele, V.A. Rassolov, P.E. Maslen, P.P. Korambath, R.D. Adamson, B. Austin, J. Baker, E.F.C. Byrd, H. Dachsel, R.J. Doerksen, A. Dreuw, B.D. Dunietz, A.D. Dutoi, T.R. Furlani, S.R. Gwaltney, A. Heyden, S. Hirata, C.P. Hsu, G. Kedziora, R.Z. Khalliulin, P. Klunzinger, A.M. Lee, M.S. Lee, W.Z. Liang, I. Lotan, N. Nair, B. Peters, E.I. Proynov, P.A. Pieniazek, Y.M. Rhee, J. Ritchie, E. Rosta, C.D. Sherrill, A.C. Simmonett, J.E. Subotnik, H.L. Woodcock III, W. Zhang, A.T. Bell, A.K. Chakraborty, D.M. Chipman, F.J. Keil, A. Warshel, W.J. Hehre, H.F. Schaefer III, J. Kong, A.I. Krylov, P.M.W. Gilla, and M. Head-Gordon Phys. Chem. Chem. Phys. 8 2006 3172 3191