Abstract
Three novel triazole Schiff-bases derivatives bearing coumarin units have been synthesised from 3,5-diaryl-4-amino-1,2,4-triazole with three kinds of coumarin aldehydes. The UV-Vis absorption and fluorescence emission spectra of (E)-4-((3,5-diphenyl-4H-1,2,4-triazol-4-ylimino)methyl)-7-methoxy-2H-chromen-2-one exhibited blue-shifted absorption and fluorescent enhancement upon chelation to zinc ion as a 2: 1 ligand-to-metal complex with a binding constant of 3.29 × 106 M−1.
References
1.
Wong B.A.
,
Friedle S.
, and
Lippard S.J.
, Inorg. Chem. , 2009 , 48 , 7009 .
2.
Wang W.
,
Jiang X.Y.
,
Zhang Q.
,
Li M.Z.
,
Yu X.L.
,
Wang J.W.
, and
Gao Y.
, J. Chem. Res. , 2013 , 37 , 662 .
3.
Zhao B.
,
Zhou Y.C.
,
Fan M.J.
,
Li Z.Y.
,
Wang L.Y.
, and
Deng Q.G.
, Chin. Chem. Lett. , 2006 , 71 , 4308 .
4.
Pathak R.K.
,
Hinge V.K.
,
Rai A.
,
Panda D.
, and
Rao C.P.
, Inorg. Chem. , 2012 , 51 , 4994 .
5.
Hagimori M.
,
Uto T.
,
Mizuyama N.
,
Temma T.
,
Yamaguchi Y.
,
Tominaga Y.
, and
Saji H.
, Sens. Actuat. B. , 2013 , 181 , 823 .
6.
Xu Z.
,
Kim G.H.
,
Han S.J.
,
Jou M.J.
,
Lee C.
,
Shin I.
, and
Yoon J.
, Tetrahedron , 2009 , 65 , 2307 .
7.
Li K.
, and
Tong A.
Sens. Actuat. B. , 2013 , 184 , 248 .
8.
Kim H.J.
,
Park S.Y.
,
Yoon S.
, and
Kim J.S.
, Tetrahedron , 2008 , 64 , 1294 .
9.
Shellaiah M.
,
Wu Y.H.H.
, and
Lin C.
, Analyst , 2013 , 138 , 2931 .
10.
Bhalla V.
,
Kumar R.
, and
Kumar M.
, Dalton. Trans. , 2013 , 42 , 975 .
11.
Gao C.
,
Jin X.
,
Yan X.
,
An P.
,
Zhang Y.
,
Liu L.
,
Tian H.
,
Liu W.
,
Yao X.
, and
Tang Y.
, Sens. Actuat. B. , 2013 , 176 , 775 .
12.
Yukio I.
,
Naoto H.
, and
Akikazu K.
, Heterocycl. Commun. , 2002 , 8 , 439 .
13.
Bender D.R.
,
Kanne D.
,
Frazier J.D.
, and
Rapoport H.
, J. Org. Chem. , 1983 , 48 , 2709 .