Abstract
Three new 5-ferrocenylisophthalicdiacyl hydrazones derivatives (molecular tweezers), have been prepared by condensation reactions of 5-ferrocenylisophthalic dihydrazide with the corresponding aromatic aldehyde. The compounds were fully characterised by spectroscopic techniques, mass spectrometry, cyclic voltammetry and an X-ray crystal structure of one example. Electrochemical investigations have demonstrated that addition of H2PO4- resulted in large shifts of respective Fc/Fc+ redox coupled to more negative potentials, indicating that these compounds have a good ability to recognise H2PO4-.
Keywords
References
1.
Schmidtchen F.P.
, and
Berger M.
, Chem. Rev. , 1997 , 97 , 1609 .
2.
Beer P.D.
, and
Gale P.A.
, Angew. Chem. Int. Ed. , 2001 , 40 , 486 .
3.
Martínez-Máñez R.
, and
Sancenón F.
, Chem. Rev. , 2003 , 103 , 4419 .
4.
Kuo L.J.
,
Liao J.H.
,
Chen C.T.
,
Huang C.H.
,
Chen C.S.
, and
Fang J.M.
, Org. Lett. , 2003 , 5 , 1821 .
5.
Westwood J.
,
Coles S.J.
,
Collinson S.R.
, et al., Organometallics , 2004 , 23 , 946 .
6.
Evans A.J.
,
Matthews S.E.
,
Cowley A.R.
, and
Beer P.D.
, Dalton Trans. , 2003 , 4644 .
7.
Moriuchi T.
,
Yoshida K.
, and
Hirao T.
, Org. Lett. , 2003 , 5 , 4285 .
8.
Sutcliffe O.B.
,
Chesney A.
, and
Bryce M.R.
, J. Organomet. Chem. , 2001 , 637–639 , 134 .
9.
Sessler J.L.
,
Zimmerman R.S.
,
Kirkovits G.J.
,
Gebauer A.
, and
Scherer M.
, J. Organomet. Chem. , 2001 , 637–639 , 343 .
10.
Saweczko P.
,
Enright G.D.
, and
Kraatz H.B.
, Inorg. Chem. , 2001 , 40 , 4409 .
11.
Balzani V.
,
Bandmann H.
,
Ceroni P.
, et al., J. Am. Chem. Soc. , 2006 , 128 , 637 .
12.
Lee D.H.
,
Lee H.Y.
,
Lee K.H.
, and
Hong J.I.
, Chem. Comm. , 2001 , 13 , 1188 .
13.
Collado D.
,
Perez-Inestrosa E.
,
Suau R.
,
Desvergne J.P.
, and
Bouas-Laurent H.
, Org. Lett. , 2002 , 4 , 855 .
14.
Hutchings M.G.
,
Grossel M.C.
,
Merckel D.A.S.
, et al., Crystal Growth Des. , 2001 , 1 , 339 .
15.
Collinson S.R.
,
Tucker J.H.R.
,
Gelbrich T.
, and
Hursthouse M.B.
, Chem. Commun. , 2001 , 6 , 555 .
16.
Butler I.R.
,
Woldt B.
,
Oh M.Z.
, and
Williams D.J.
, Inorg. Chem. Comm. , 2006 , 9 , 1255 .
17.
Koridze A.A.
,
Kuklin S.A.
,
Sheloumov A.M.
, et al., Organometallics , 2004 , 23 , 4585 .
18.
Kasasahara A.
,
Izumi T.
, and
Yoshida Y.
, Bull. Chem., Soc. Jpn , 1982 , 55 , 1901 .
19.
Beer P.D.
,
Gale P.A.
, and
Chen G.Z.
, J. Chem. Soc., Dalton Trans. , 1999 , 1897 .
20.
Beer P.D.
,
Gale P.A.
, and
Chen G.Z.
, Coord. Chem. Rev. , 1999 , 185–186 , 3 .
21.
Beer P.D.
, and
Hayes E.J.
, Coord. Chem. Rev. , 2003 , 240 , 167 .
22.
Lankshear M.D.
, and
Beer P.D.
, Coord. Chem. Rev. , 2006 , 250 , 3142 .
23.
Beer P.D.
, and
Gale P.A.
, Angew. Chem. Int. Ed. , 2001 , 40 , 486 .
24.
Liu W.
,
Zheng H.J.
,
Chen B.Y.
,
Du L.Z.
, and
Song M.P.
, Z. Anorg. Allg. Chem. , 2010 , 636 , 236 .
25.
Savage D.
,
Gallagher J.F.
,
Ida Y.
, and
Kenny P.T.M.
, Inorg. Chem. Commun. , 2002 , 5 , 1034 .
26.
Sheldrick G.M.
, SHELX-97: Program for Crystal Structure Analysis: Crystal Structure Determination (SHELXS) , University of Göttingen , Germany , 1997 .
27.
Sheldrick G.M.
, SHELX-97: Program for Crystal Structure Analysis: Structure Refinement (SHELXL) , University of Göttingen , Germany , 1997 .
28.
Ye B.X.
,
Xu Y.
,
Wang F.
,
Fu Y.
, and
Song M.P.
, Inorg. Chem. Commun. , 2005 , 8 , 44 .
29.
Goel A.
,
Brennan N.
,
Brady N.
, and
Kenny P.T.M.
, Biosens. Bioelectro. , 2007 , 22 , 2047 .
30.
Reynes O.
,
Maillard F.
,
Moutet J.C.
, et al., J. Organomet. Chem. , 2001 , 637–639 , 356 .
31.
Stone D.L.
, and
Smith D.K.
, Polyhedron , 2003 , 22 , 763 .
32.
Chen Z.
,
Graydon A.R.
, and
Beer P.D.
, J. Chem. Soc., Faraday Trans. , 1996 , 92 , 97 .
33.
Otón F.
,
Tarraga A.
,
Espinosa A.
,
Velasco M.D.
, and
Molina P.
, J. Org. Chem. , 2006 , 71 , 4590 .
34.
Serr B.R.
,
Andersen K.A.
,
Elliot C.M.
, and
Anderson O.P.
, Inorg. Chem. , 1988 , 27 , 4499 .
35.
Richardson D.E.
, and
Taube H.
, Inorg. Chem. , 1981 , 20 , 1278 .
