An NHC silver(I) macrometallocycle: synthesis, structure and selective recognition of iodide anions

A bis-benzimidazolium salt with oligoether-linker LH2·(PF6)2 and its 13-membered N-heterocyclic carbene silver(I) crown ether 1 have been synthesized and characterized. The coordination geometry of the silver(I) ion of 1 is nearly linear with a C(7)–Ag(1)–C(23) bond angle of 179.6(1)°. In the crystal packing of 1, a 2D supramolecular layer is formed by π–π stacking interactions from benzimidazole rings. In particular, the selective recognition of I− using 1 as a receptor was studied on the basis of fluorescence and UV/vis spectroscopic titrations.

[1]  M. R. Gonçalves,et al.  Synthesis, characterization, photophysical and electrochemical properties of fac-tricarbonyl(4,7-dichloro-1,10-phenanthroline)rhenium(I) complexes , 2015 .

[2]  Yonghong Hu,et al.  Phenothiazine–aminothiourea–Hg(II) ensemble-based fluorescence turn-on toward iodide in aqueous media and imaging application in live cells , 2015 .

[3]  M. Ocak,et al.  New calix[4]arene based highly selective fluorescent probe for Al3+ and I− , 2015 .

[4]  Katsuhiko Mitachi,et al.  Chemoenzymatic syntheses of water-soluble lipid I fluorescent probes. , 2015, Tetrahedron letters.

[5]  B. Sarrión,et al.  Fluorescence quenching of 1-pyrene-carboxaldehyde by iodide ions in the presence of anionic (SDS) and cationic (CTAC) micelles: a quantitative treatment , 2015 .

[6]  B. Nair,et al.  Bibenzimidazole containing mixed ligand cobalt(III) complex as a selective receptor for iodide , 2014 .

[7]  Qiang Li,et al.  Synthesis of N-heterocyclic carbene silver and palladium complexes bearing bis(pyrazol-1-yl)methyl moieties , 2013 .

[8]  Benjamin D. Ward,et al.  Reactivity of Tetrabutylammonium Iodide with a Heteronuclear 6Copper(II)–4Na(I) Complex: Selective Recognition of Iodide Ion , 2013 .

[9]  Xiaolong Liu,et al.  Dinuclear Copper(I) Complexes of Phenanthrolinyl-Functionalized NHC Ligands , 2013 .

[10]  Xin Li,et al.  Synthesis and structural characterization of N-heterocyclic carbene silver complexes derived from N-ferrocenylmethyl-N′-(pyridylmethyl)imidazolium iodides , 2013 .

[11]  E. Garcı́a-España,et al.  Boehmite Supported Pyrene Polyamine Systems as Probes for Iodide Recognition , 2013 .

[12]  Chirantan Kar,et al.  Benzimidazole functionalized tripodal receptor for selective recognition of iodide , 2012 .

[13]  Neeraj K. Joshi,et al.  Fluorescence characteristics of 5-amino salicylic acid: An iodide recognition study. , 2012, Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy.

[14]  I. Youn,et al.  An imidazolium-based fluorescent cyclophane for the selective recognition of iodide. , 2012, Chemistry, an Asian journal.

[15]  Bahareh Shirinfar,et al.  Fluorescent imidazolium-based cyclophane for detection of guanosine-5'-triphosphate and I(-) in aqueous solution of physiological pH. , 2011, Organic letters.

[16]  Zhaoquan Yao,et al.  Two N-Heterocyclic Carbene Silver(I) Cyclophanes: Synthesis, Structural Studies, and Recognition for p-Phenylenediamine , 2011 .

[17]  Narinder Singh,et al.  Chromogenic and fluorescent recognition of iodide with a benzimidazole-based tripodal receptor. , 2011, Organic letters.

[18]  Shanshan Huang,et al.  Highly sensitive and selective fluorescent chemosensor for Ag+ based on a coumarin-Se2N chelating conjugate. , 2011, Chemical communications.

[19]  H. Fun,et al.  Recognition of carboxylate anions and carboxylic acids by selenium-based new chromogenic fluorescent sensor: a remarkable fluorescence enhancement of hindered carboxylates. , 2009, Organic Letters.

[20]  Wanzhi Chen,et al.  Direct synthesis of iron, cobalt, nickel, and copper complexes of N-heterocyclic carbenes by using commercially available metal powders. , 2009, Angewandte Chemie.

[21]  Y. Qiu,et al.  Palladium(II)−N-Heterocyclic Carbene Metallacrown Ether Complexes: Synthesis, Structure, and Catalytic Activity in the Suzuki−Miyaura Reaction , 2009 .

[22]  J. Sessler,et al.  Selective sensing of anions with calix[4]pyrroles strapped with chromogenic dipyrrolylquinoxalines. , 2009, The Journal of organic chemistry.

[23]  Philip A. Gale,et al.  Anion receptor chemistry: highlights from 2007. , 2009, Chemical Society reviews.

[24]  Nahid Pourreza,et al.  An optical redox chemical sensor for determination of iodide. , 2009, Talanta.

[25]  Narinder Singh,et al.  Cu(II) complex of a flexible tripodal receptor as a highly selective fluorescent probe for iodide , 2009 .

[26]  Cuiping Han,et al.  Synthesis of cadmium selenide quantum dots modified with thiourea type ligands as fluorescent probes for iodide ions , 2008 .

[27]  Zunsheng Cai,et al.  Study on acetate ion recognition and sensing in aqueous media using a novel and simple colorimetric sensor and its analytical application. , 2008, Talanta.

[28]  F. Hahn,et al.  Heterocyclic carbenes: synthesis and coordination chemistry. , 2008, Angewandte Chemie.

[29]  Ashutosh Kumar Singh,et al.  Polymeric membrane sensors based on Cd(II) Schiff base complexes for selective iodide determination in environmental and medicinal samples. , 2008, Talanta.

[30]  E. Akkaya,et al.  A monostyryl-boradiazaindacene (BODIPY) derivative as colorimetric and fluorescent probe for cyanide ions. , 2008, Organic letters.

[31]  Philip A. Gale,et al.  Anion receptors based on organic frameworks: highlights from 2005 and 2006. , 2008, Chemical Society reviews.

[32]  Xudong Yu,et al.  Color responses of novel receptors for AcO− and a test paper for AcO− in pure aqueous solution , 2007 .

[33]  Narinder Singh,et al.  Benzimidazole-based tripodal receptor: highly selective fluorescent chemosensor for iodide in aqueous solution. , 2007, Organic letters.

[34]  Jianzhang Zhao,et al.  Simple bis-thiocarbono-hydrazones as sensitive, selective, colorimetric, and switch-on fluorescent chemosensors for fluoride anions. , 2007, Chemistry.

[35]  I. J. Lin,et al.  Preparation and application of N-heterocyclic carbene complexes of Ag(I) , 2007 .

[36]  F. Hahn,et al.  Synthesis of pincer-type bis(benzimidazolin-2-ylidene) palladium complexes and their application in C-C coupling reactions , 2007 .

[37]  A. Bianchi,et al.  Anion coordination chemistry in aqueous solution of polyammonium receptors , 2006 .

[38]  Md. Alamgir Hossain,et al.  Influence of dimensionality and charge on anion binding in amide-based macrocyclic receptors , 2006 .

[39]  A. P. Davis,et al.  Anion binding and transport by steroid-based receptors , 2006 .

[40]  S. Valiyaveettil,et al.  Carbazole-Containing Conjugated Copolymers as Colorimetric/Fluorimetric Sensor for Iodide Anion , 2006 .

[41]  K. Cavell,et al.  Silver(I) and Palladium(II) Complexes of an Ether-Functionalized Quasi-pincer Bis-carbene Ligand and Its Alkyl Analogue , 2006 .

[42]  Xiangjian Wan,et al.  Effectively selective fluorescent chemosensor for terephthalate , 2006 .

[43]  A. O. Patrocinio,et al.  Light driven trans-to-cis isomerization of stilbene-like ligands in fac-[Re(CO)3(NN)(trans-L)]+ and luminescence of their photoproducts , 2006 .

[44]  Angelo Taglietti,et al.  Some guidelines for the design of anion receptors , 2006 .

[45]  Qing-Shan Li,et al.  Synthetic and Structural Studies of Silver(I)‐ and Gold(I)‐ContainingN‐Heterocyclic Carbene Metallacrown Ethers , 2006 .

[46]  Qiang Feng,et al.  Novel hexadentate imidazolium salts in the rhodium-catalyzed addition of arylboronic acids to aldehydes , 2006 .

[47]  W. Youngs,et al.  Ag(I) N-heterocyclic carbene complexes: synthesis, structure, and application. , 2005, Chemical reviews.

[48]  J. Veciana,et al.  Highly selective chromogenic and redox or fluorescent sensors of Hg2+ in aqueous environment based on 1,4-disubstituted azines. , 2005, Journal of the American Chemical Society.

[49]  Leroy Cronin,et al.  The importance of π–π, π–CH and N–CH interactions in the crystal packing of Schiff-base derivatives of cis,cis- and cis,trans-1,3,5-triaminocyclohexane , 2005 .

[50]  M. Alcarazo,et al.  Imidazo[1,5-a]pyridine: a versatile architecture for stable N-heterocyclic carbenes. , 2005, Journal of the American Chemical Society.

[51]  A. Ajayaghosh,et al.  Selective calcium ion sensing with a bichromophoric squaraine foldamer. , 2005, Journal of the American Chemical Society.

[52]  Meining Wang,et al.  Synthesis, structure, and [60]fullerene complexation properties of azacalix[m]arene[n]pyridines. , 2004, Angewandte Chemie.

[53]  M. Leclerc,et al.  New colorimetric and fluorometric chemosensor based on a cationic polythiophene derivative for iodide-specific detection. , 2003, Journal of the American Chemical Society.

[54]  K. Cavell,et al.  A pyridine bridged dicarbene ligand and its silver(I) and palladium(II) complexes: synthesis, structures, and catalytic applications ☆ , 2002 .

[55]  B. de Benoist,et al.  Iodine deficiency in the world: where do we stand at the turn of the century? , 2001, Thyroid : official journal of the American Thyroid Association.

[56]  J. Dunn Correcting iodine deficiency is more than just spreading around a lot of iodine. , 2001, Thyroid : official journal of the American Thyroid Association.

[57]  Philip A. Gale,et al.  Anion Recognition and Sensing: The State of the Art and Future Perspectives. , 2001, Angewandte Chemie.

[58]  Gutsche,et al.  Complexation of fullerenes with 5,5'-Biscalix , 2000, The Journal of organic chemistry.

[59]  Philip A. Gale Anion coordination and anion-directed assembly: highlights from 1997 and 1998 , 2000 .

[60]  A. Danopoulos,et al.  N-Functionalised heterocyclic carbene complexes of silver , 2000 .

[61]  Fritz Vögtle,et al.  High-Yielding Rotaxane Synthesis with an Anion Template. , 1999, Angewandte Chemie.

[62]  P. Bühlmann,et al.  Carrier-Based Ion-Selective Electrodes and Bulk Optodes. 2. Ionophores for Potentiometric and Optical Sensors. , 1998, Chemical reviews.

[63]  E. Kool Preorganization of DNA: Design Principles for Improving Nucleic Acid Recognition by Synthetic Oligonucleotides. , 1997, Chemical reviews.

[64]  J. Sessler,et al.  Molecular recognition via base-pairing and phosphate chelation. Ditopic and tritopic sapphyrin-based receptors for the recognition and transport of nucleotide monophosphates , 1995 .