Synthesis and Characterization of Electroactive Ferrocene Derivatives: Ferrocenylimidazoquinazoline as a Multichannel Chemosensor Selectively for Hg2+ and Pb2+ Ions in an Aqueous Environment

被引：91

作者：

Pandey, Rampal ^{[1
]}

Gupta, Rakesh Kumar ^{[1
]}

Shahid, Mohammad ^{[1
]}

Maiti, Biswajit ^{[1
]}

Misra, Arvind ^{[1
]}

Pandey, Daya Shankar ^{[1
]}

机构：

[1] Banaras Hindu Univ, Fac Sci, Dept Chem, Varanasi 221005, Uttar Pradesh, India

来源：

INORGANIC CHEMISTRY | 2012年 / 51卷 / 01期

关键词：

EFFECTIVE CORE POTENTIALS; NUCLEOPHILIC AROMATIC-SUBSTITUTION; ASYMMETRIC AUTOCATALYSIS; MOLECULAR CALCULATIONS; BIOORGANOMETALLIC CHEMISTRY; FLUORESCENCE; METAL; MERCURY; LEAD; RECOGNITION;

D O I：

10.1021/ic201663m

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The synthesis and characterization of ferrocene (Fc) derivatives 4[2,5-diferrocenyl-4-(4-pyridyl)imidazolidin-1-yl-methyl]pyridine (1), ferrocenylmethylenepyridin-3-ylmethylamine (2), N,N'-bis(ferrocenylmethylene)-2,4,6-trimethylbenzene-1,3-diamine (3), and 6-ferrocenyl-5,6-dihydro[4,5]imidazo[1,2-c]quinazoline (4) have been described. Structures of 1, 2, and 4 have been determined by single-crystal X-ray diffraction analyses. At 25 degrees C, 1-3 are nonfluorescent, while 4 displays moderate fluorescence and chromogenic, fluorogenic, and electrochemical sensing selectively toward Hg2+ and Pb2+ ions. Association constants (K-a) for Hg2+ and Pb2+ have been determined by the Benesi-Hildebrand method. Job's plot analysis supported 1:1 and 1:2 stoichiometries for Hg2+ and Pb2+ ions. Cyclic voltammograms of 1-4 exhibited reversible waves corresponding to a ferrocene/ferrocenium couple. The wave associated with 4 (+0.0263 V) exhibited positive (Delta E-pa = 0.136 V) and negative (Delta E-pa = 0.025 V) shifts in the presence of Hg2+ and Pb2+ ions, respectively. The mode of interaction between metal ions and 4 has been supported by H-1 NMR spectroscopy and mass spectrometry studies and verified by theoretical studies. It presents the first report dealing with ferrocene-substituted quinazoline as a multichannel chemosensor for Hg2+/Pb2+ ions.

引用

页码：298 / 311

页数：14

共 121 条

[1] Thiomethoxychalcone-Functionalized Ferrocene Ligands as Selective Chemodosimeters for Mercury(II): Single-Crystal X-ray Structural Signature of the [Hg8(μ8-S)(SCH3)12]2+ Cluster [J].