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Synthesis of Redox-Active Macrocyclic Diimine Ligands as Flexible Building Blocks
Corresponding Author(s) : Jian-Fei Kong
Asian Journal of Chemistry,
Vol. 25 No. 6 (2013): Vol 25 Issue 6
Abstract
Large macrocyclic compounds have proven themselves as important building blocks in molecular design due to their interesting structures and properties. Application of these compounds to molecular machines and devices has also attracted much attention. A muti-step synthesis was successfully accomplished to obtain the bipyridyl containing macrocyclic ligand with potential redox-activities. The possible controllable binding properties of these compounds will examined later on. Subsequent coordination of the ligands to suitable transition metal centers and examination for the potential communications between these meal centers is also undergoing.
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References
(a) G.W. Gokel, W.M. Leevy and M.E. Weber, Chem. Rev., 104, 2723 (2004); (b) S.E. Gibson and C. Lecci,Angew. Chem. Int. Ed., 45, 1364 (2006).
(a) S.S. Moore, T.L. Tarnowski, M. Newcomb and D.J. Cram, J. Am. Chem. Soc., 99, 6398 (1977); (b) M. Newcomb, J.L. Toner, R.C. Helgeson and D.J. Cram, J. Am. Chem. Soc., 101, 4941 (1979).
(a) I.L. Karle, D. Ranganathan and V. Haridas, J. Am. Chem. Soc., 118, 10916 (1996); (b) D. Ranganathan, V. Haridas, K.P. Madhusudanan, R. Roy, R. Nagaraj and G.B. John, J. Am. Chem. Soc., 119, 11578 (1997).
E.J. de Vries and R.M. Kellogg, J. Chem. Soc. Chem. Commun., 238 (1993).
J. Becerril, M.I. Burguete, B. Escuder, S.V. Luis, J.F. Miravet and M. Querol, Chem. Commun., 738 (2002).
X.X. Zhang, J.S. Bradshaw and R.M. Izatt, Chem. Rev., 97, 3313 (1997).
(a) Y. Cui, S.J. Lee and W. Lin, J. Am. Chem. Soc., 125, 6014 (2003); (b) Y.H. Luo, H.W. Liu, F. Xi, L. Li, X.G. Jin, C.C. Han and C.M. Chan, J. Am. Chem. Soc., 125, 6447 (2003).
Q. Sun, H. Wang, C. Yang and Y. Li, J. Mater. Chem., 13, 800 (2003).
(a) G.M. Dykes, D.K. Smith and G.J. Seeley, Angew. Chem. Int. Ed., 41, 3254 (2002), (b) P.R. Ashton, I. Baxter, M.C.T. Fyfe, F.M. Raymo, N. Spencer, J.F. Stoddart, A.J.P. White and D.J. Williams, J. Am. Chem. Soc., 120, 2297 (1998); (c) R. Nonokawa and E. Yashima, J. Am. Chem. Soc., 125, 1278 (2003).
M.A. Krasnow, A. Stasiak, S.J. Spengler, F. Dean, T. Koller and N.R. Cozzarelli, Nature, 304, 559 (1983).
(a) P.L. Anelli, P.R. Ashton, R. Ballardini, V. Balzani, M. Delgado, M. Gandolfi, T.T. Goodnow, A.E. Kaifer, D. Philip, M. Pietraszkiewicz, L. Prodi, M.V. Reddington, A.M.Z. Slawin, N. Spencer, J.F. Stoddart, C. Vincent and D.J. Williams, J. Am. Chem. Soc., 114, 193 (1992); O.S.M. Nasman, Asian J. Chem., 19, 1231 (2007); (b) D.B. Amabilino,
P.R. Ashton, C.L. Brown, E. Cordova, L.A. Godinez, T.T. Goodnow, A.E. Kaifer, S.P. Newton, M. Pietraszkiewicz, D. Philp, F.M. Raymo, A.S. Reder, M.T. Rutland, A.M.Z. Slawin, N. Spencer, J.F. Stoddart and D.J. Williams, J. Am. Chem. Soc., 117, 1271 (1995); (c) P.D. Beer, A.R. Cowley, J.C. Jeffery, R.L. Paul and W.W.H. Wong, Polyhedron, 22, 795 (2003).
T. Nabeshima, Tetrahedron, 59, 639 (2003).
T. Nabeshima, H. Furusawa and Y. Yano, Angew. Chem. Int. Ed., 33, 1750 (1994).
M. Von Delius, E.M. Geertsema, D.A. Leigh and A.M.Z. Slawin, Org. Biomol. Chem., 8, 4617 (2010).
D.D. Perrin and W.L.F. Armarego, Purification of Laboratory Chemicals, edn. 3 (1996).
F. Tellier, R. Sauvetre and J.-F. Normant, J. Organomet. Chem., 292, 19 (1985).
P.F.H. Schwab, F. Fleischer and J. Michl, J. Org. Chem., 67, 443 (2002).
(a) D. Wenkert and R.B. Woodward, J. Org. Chem., 48, 283 (1983); (b) A.M.D. Egbe, A.M. Amer and E. Klemm, Des. Monomers Polym., 4, 169 (2001).
H.M. Relles and G. Pizzolato, J. Org. Chem., 33, 2249 (1968).
R.N. Young, J.Y. Gauthier and W. Coombs, Tetrahedron Lett., 25, 1753 (1984).