Bisthiocarbohydrazones as Colorimetric and "Turn on" Fluorescent Chemosensors for Selective Recognition of Fluoride

被引：33

作者：

Kumar, Saravana Loganathan Ashok ^{[1
]}

Tamilarasan, Ramalingam ^{[1
]}

Kumar, Moorthy Saravana ^{[1
]}

Sreekanth, Anandram ^{[1
]}

机构：

[1] Natl Inst Technol, Dept Chem, Tiruchirappalli 620015, Tamil Nadu, India

来源：

INDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH | 2011年 / 50卷 / 22期

关键词：

ANIONS;

D O I：

10.1021/ie2013696

中图分类号：

TQ [化学工业];

学科分类号：

0817 ;

摘要：

Bisthiocarbohydrazone derivatives of two heterocyclic ketones Were designed and synthesized to selectively sense, fluoride ion from a biologically competing solvent dimethylsulfoxide(DMSO). The selective recognition of fluoride IS clearly visible to the naked eye with a distinct color change. The recognition mechanism has been investigated by UV-visible, fluorescence spectroscopy, and H-1 NMR titration experiments. From the Benesi-Hidebrand equation and Job's plot, it Was inferred that both compounds bind to fluoride With a 1:1 stoichiometry. H-1 NMR titration data indicates deprotonation of the NH protons by fluoride as a prominent step in the recognition.

引用

页码：12379 / 12383

页数：5

共 17 条

[1] pH as a trigger of peptide β-sheet self-assembly and reversible switching between nematic and isotropic phases [J].

Aggeli, A ;

Bell, M ;

Carrick, LM ;

Fishwick, CWG ;

Harding, R ;

Mawer, PJ ;

Radford, SE ;

Strong, AE ;

Boden, N .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (32) :9619-9628

[2] What anions do to N-H-containing receptors [J].

Amendola, Valeria ;

Esteban-Gomez, David ;

Fabbrizzi, Luigi ;

Licchelli, Maurizio .

ACCOUNTS OF CHEMICAL RESEARCH, 2006, 39 (05) :343-353

[3] Antimicrobial and mutagenic activity of some carbono-and thiocarbonohydrazone ligands and their copper(II), iron(II) and zinc(II) complexes [J].

Bacchi, A ;

Carcelli, M ;

Pelagatti, P ;

Pelizzi, C ;

Pelizzi, G ;

Zani, F .

JOURNAL OF INORGANIC BIOCHEMISTRY, 1999, 75 (02) :123-133

[4] Highly selective optical fluoride ion sensor with submicromolar detection limit based on aluminum(III) octaethylporphyrin in thin polymeric film [J].

Badr, IHA ;

Meyerhoff, ME .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (15) :5318-5319

[5] Nature of urea-fluoride interaction:: Incipient and definitive proton transfer [J].

Boiocchi, M ;

Del Boca, L ;

Gómez, DE ;

Fabbrizzi, L ;

Licchelli, M ;

Monzani, E .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (50) :16507-16514

[6] (Benzylideneamino)thioureas - Chromogenic interactions with anions and N-H deprotonation [J].

Bonizzoni, Marco ;

Fabbrizzi, Luigi ;

Taglietti, Angelo ;

Tiengo, Federico .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (16) :3567-3574

[7] Why, on interaction of urea-based receptors with fluoride, beautiful colors develop [J].

Esteban-Gómez, D ;

Fabbrizzi, L ;

Licchelli, M .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (14) :5717-5720

[8] Colorimetric and fluorescence sensing of anions using thiourea based coumarin receptors [J].

Ghosh, Kumaresh ;

Adhikari, Surnan .

TETRAHEDRON LETTERS, 2006, 47 (46) :8165-8169

[9] Simple bisthiocarbonohydrazones as sensitive, selective, colorimetric, and switch-on fluorescent chemosensors for fluoride anions [J].

Han, Feng ;

Bao, Yuhui ;

Yang, Zhigang ;

Fyles, Thomas M. ;

Zhao, Jianzhang ;

Peng, Xiaojun ;

Fan, Jiangli ;

Wu, Yunkou ;

Sun, Shiguo .

CHEMISTRY-A EUROPEAN JOURNAL, 2007, 13 (10) :2880-2892

[10] Fluorescence "turn-on" sensing of carboxylate anions with oligothiophene-based o-(carboxamido)trifluoroacetophenones [J].

Kim, Dae-Sik ;

Ahn, Kyo Han .

JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (17) :6831-6834

← 1 2 →