Size and temperature dependent encapsulation of tetrahedral anions by a protonated cryptand host

The protonated cryptand L shows both size and temperature dependent encapsulation for tetrahedral ClO4− and H2PO4− anions (L = N[(CH2)2NHCH2(C6H4-p)CH2NH(CH2)2]3N). The crystal structures of perchlorate complex [(H6L)(ClO4)][ClO4]5(H2O)7(CH3CN) (1) and phosphate complex [(H8L)(H2O)3][H2PO4]8(H2O)9 (2) showed that the smaller ClO4− can facilely enter into the cavity of H6L6+, while the larger H2PO4− can not be encapsulated inside the cavity of H6L6+ and H8L8+ at room temperature. Upon heating, however, H2PO4− can be encapsulated into the cavity of H8L8+ to generate a complex of [(H8L)(H2PO4)][H2PO4]7(H2O)18 (3), and the encapsulated H2PO4− can be released by increasing the pH value to 2.

[1]  T. Lu,et al.  Anion Dependent Water Clusters Encapsulated Inside a Cryptand Cavity , 2008 .

[2]  Philip A. Gale,et al.  1,3-Diindolylureas: high affinity dihydrogen phosphate receptors. , 2008, Chemical communications.

[3]  E. Suresh,et al.  Molecular Recognition Studies of an Octaaminocryptand upon Different Degree of Protonation , 2008 .

[4]  T. Lu,et al.  Unusual pH value dependent encapsulation and release of water–methanol binary guests by a cryptand host , 2008 .

[5]  P. Gatseva,et al.  Iodine status and goitre prevalence in nitrate-exposed schoolchildren living in rural Bulgaria. , 2008, Public health.

[6]  E. Bakker,et al.  Phosphate-selective fluorescent sensing microspheres based on uranyl salophene ionophores. , 2008, Analytica chimica acta.

[7]  P. Molina,et al.  Cation coordination induced modulation of the anion sensing properties of a ferrocene-imidazophenanthroline dyad: multichannel recognition from phosphate-related to chloride anions. , 2008, The Journal of organic chemistry.

[8]  Qiang Yang,et al.  Preparation of N,N'-bisethoxyethane[12]amideferrocenophane and its application in anion recognition. , 2008, The journal of physical chemistry. B.

[9]  Biao Wu,et al.  Sulfate ion encapsulation in caged supramolecular structures assembled by second-sphere coordination. , 2008, Chemical communications.

[10]  T. Lu,et al.  Anion recognition of chloride and bromide by a rigid dicobalt(II) cryptate. , 2008, Inorganic chemistry.

[11]  S. Singh,et al.  Calix[4]arene based neutral receptor for dihydrogen phosphate anion , 2008 .

[12]  Anjul Kumar,et al.  Anion recognition by 1,2,3-triazolium receptors: application of click chemistry in anion recognition. , 2008, Organic letters.

[13]  Ismail Abbas,et al.  Modified calix[4]pyrrole receptor: solution thermodynamics of anion complexation and a preliminary account on the phosphate extraction ability of its oligomer. , 2007, The journal of physical chemistry. B.

[14]  T. Lu,et al.  CO2 fixation and transformation by a dinuclear copper cryptate under acidic conditions. , 2007, Chemistry, an Asian journal.

[15]  Juyoung Yoon,et al.  A highly selective fluorescent chemosensor for dihydrogen phosphate via unique excimer formation and PET mechanism , 2007 .

[16]  E. Suresh,et al.  Recognition of water-acetonitrile-water cluster in a tetraprotonated picrate salt of octaaminocryptand , 2006 .

[17]  W. Cresko,et al.  Perchlorate induces hermaphroditism in threespine sticklebacks , 2006, Environmental toxicology and chemistry.

[18]  E. Suresh,et al.  A hybrid water-chloride structure with discrete undecameric water moieties self-assembled in a heptaprotonated octaamino cryptand. , 2006, Angewandte Chemie.

[19]  Philip A. Gale,et al.  Structural and molecular recognition studies with acyclic anion receptors. , 2006, Accounts of chemical research.

[20]  Juyoung Yoon,et al.  Imidazolium receptors for the recognition of anions. , 2006, Chemical Society reviews.

[21]  D. Powell,et al.  Anion binding motifs: topicity and charge in amidocryptands. , 2005, Journal of the American Chemical Society.

[22]  P. Ghosh,et al.  Counteranion-controlled water cluster recognition in a protonated octaamino cryptand. , 2005, Inorganic chemistry.

[23]  K. Bowman-James Alfred Werner revisited: the coordination chemistry of anions. , 2005, Accounts of chemical research.

[24]  R. C. Moore,et al.  Accumulation and perchlorate exposure potential of lettuce produced in the Lower Colorado River region. , 2005, Journal of agricultural and food chemistry.

[25]  Md. Alamgir Hossain,et al.  Tritopic (cascade) and ditopic complexes of halides with an azacryptand. , 2005, Inorganic chemistry.

[26]  Md. Alamgir Hossain,et al.  Encapsulated sulfates: insight to binding propensities. , 2005, Chemical communications.

[27]  Philip A. Gale,et al.  Anion binding properties of 5,5'-dicarboxamido-dipyrrolylmethanes. , 2004, Organic & biomolecular chemistry.

[28]  J. Sessler,et al.  Synthesis and study of a new diamidodipyrromethane macrocycle. An anion receptor with a high sulfate-to-nitrate binding selectivity. , 2004, Chemical communications.

[29]  Philip A. Gale,et al.  Metal-organic anion receptors: arranging urea hydrogen-bond donors to encapsulate sulfate ions. , 2004, Journal of the American Chemical Society.

[30]  T. Lu,et al.  C-C bond cleavage of acetonitrile by a dinuclear copper(II) cryptate. , 2004, Journal of the American Chemical Society.

[31]  V. McKee,et al.  Towards promising oxoanion extractants: azacages and open-chain counterparts , 2003 .

[32]  D. Nolting,et al.  A molecular oyster: a neutral anion receptor containing two cyclopeptide subunits with a remarkable sulfate affinity in aqueous solution. , 2002, Journal of the American Chemical Society.

[33]  Md. Alamgir Hossain,et al.  Parallels in cation and anion coordination: a new class of cascade complexes. , 2002, Angewandte Chemie.

[34]  V. McKee,et al.  Selectivity for dinegative versus mononegative oxoanionic guests within a cryptand host , 2001 .

[35]  O. A. Gerasimchuk,et al.  Binding of phosphate with a simple hexaaza polyammonium macrocycle. , 2000, Inorganic chemistry.

[36]  Jong‐In Hong,et al.  Oxoanion recognition by a thiouronium receptor , 1998 .

[37]  M. Licchelli,et al.  Fluorescent sensor of imidazole and histidine , 1997 .

[38]  V. Malashkevich,et al.  The Crystal Structure of a Five-Stranded Coiled Coil in COMP: A Prototype Ion Channel? , 1996, Science.

[39]  P. Beer Anion selective recognition and optical/electrochemical sensing by novel transition-metal receptor systems , 1996 .

[40]  B. Dietrich Design of anion receptors: Applications , 1993 .

[41]  Ronald L. Bruening,et al.  Thermodynamic and kinetic data for macrocycle interactions with cations and anions , 1991 .

[42]  K. B. Mertes,et al.  Polyammonium Macrocycles as Catalysts for Phosphoryl Transfer: The Evolution of an Enzyme Mimic , 1990 .

[43]  Jane Brox,et al.  6 A.M. , 1990 .

[44]  F. Quiocho,et al.  Sulphate sequestered in the sulphate-binding protein of Salmonella typhimurium is bound solely by hydrogen bonds , 1985, Nature.