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Title: A Hexahomotrioxacalix[3]arene-Based Ditopic Receptor for Alkylammonium Ions Controlled by Ag+ Ions

Journal Article · · Molecules
 [1];  [1];  [1];  [2];  [2];  [3];  [4];  [5];  [6];  [1]
  1. Saga Univ., Saga (Japan). Dept. of Applied Chemistry, Faculty of Science and Engineering
  2. Memorial Univ. of Newfoundland, St. John’s, NL (United States). Dept. of Chemistry
  3. Guizhou Univ., Guiyang (China). Key Lab. of Macrocyclic and Supramolecular Chemistry of Guizhou Province
  4. Loughborough Univ., Loughborough (United States). Chemistry Dept.
  5. Univ. of Hull, Hull, Yorkshire (United States). School of Mathematics and Physical Sciences
  6. Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States). Advanced Light Source (ALS)
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A receptor cone-1 based on a hexahomotrioxacalix[3]arene bearing three pyridyl groups was successfully synthesized, which has a C3-symmetric conformation and is capable of binding alkylammonium and metal ions simultaneously in a cooperative fashion. It can bind alkylammonium ions through the π-cavity formed by three aryl rings. This behaviour is consistent with the cone-in/cone-out conformational rearrangement needed to reorganize the cavity for endo-complexation. As a C3-symmetrical pyridyl-substituted calixarene, receptor cone-1 can also bind an Ag + ion, and the nitrogen atoms are turned towards the inside of the cavity and interact with Ag+. After complexation of tris(2-pyridylamide) derivative receptor cone-1 with Ag+, the original C3-symmetry was retained and higher complexation selectivity for n-BuNH3+ versus t-BuNH3+ was observed. Thus, it is believed that this receptor will have a role to play in the sensing, detection, and recognition of Ag+ and n-BuNH3+ ions.

Research Organization:
Lawrence Berkeley National Laboratory (LBNL), Berkeley, CA (United States)
Sponsoring Organization:
USDOE Office of Science (SC), Basic Energy Sciences (BES)
Grant/Contract Number:
AC02-05CH11231
OSTI ID:
1434008
Journal Information:
Molecules, Vol. 23, Issue 2; ISSN 1420-3049
Publisher:
MDPICopyright Statement
Country of Publication:
United States
Language:
English
Citation Metrics:
Cited by: 2 works
Citation information provided by
Web of Science

References (44)

Generalized Gradient Approximation Made Simple journal October 1996
Calixarenes: from biomimetic receptors to multivalent ligands for biomolecular recognition journal January 2010
Interlocked Macromolecules journal July 1999
Inclusion of [60]Fullerene in a Homooxacalix[3]arene-Based Dimeric Capsule Cross-Linked by a Pd II −Pyridine Interaction journal May 1999
Synthesis and Inclusion Properties ofC3-Symmetrically Capped Hexahomotrioxacalix[3]arenes with Ester Groups on the Lower Rim journal March 2001
A pyrene-functionalized triazole-linked hexahomotrioxacalix[3]arene as a fluorescent chemosensor for Zn2+ ions journal June 2016
Ab initio effective core potentials for molecular calculations. Potentials for K to Au including the outermost core orbitals journal January 1985
Synthesis, Complexation, and Membrane Transport Studies of 1,3-Alternate Calix[4]arene-crown-6 Conformers: A New Class of Cesium Selective Ionophores journal March 1995
Synthesis and evaluation of a novel pyrenyl-appended triazole-based thiacalix[4]arene as a fluorescent sensor for Ag+ ion journal May 2011
Alkyl Ammonium Ion Selectivity of Hexahomotrioxacalix[3]arene Triamide Derivative having the Intramolecular Hydrogen-Bonding Group journal November 2005
Modification of the Upper Rim of Homooxacalix[3]arenes and Complexation between a Nitrohomooxacalix[3]arene Derivative and n -Hexylamine † journal November 2002
Optical Chemosensor for Ag + , Fe 3+ , and Cysteine: Information Processing at Molecular Level journal February 2011
A Stepwise Huisgen Cycloaddition Process: Copper(I)-Catalyzed Regioselective “Ligation” of Azides and Terminal Alkynes journal July 2002
Recognition of 1,2-diazines by a bidentate Lewis acid journal January 1998
Efficient Photocurrent Generation in Novel Self-Assembled Multilayers Comprised of [60]Fullerene−Cationic Homooxacalix[3]arene Inclusion Complex and Anionic Porphyrin Polymer journal May 2001
Thiacalixarenes journal December 2006
Synthesis and ion selectivity of conformers derived from hexahomotrioxacalix[3]arene journal October 1993
BYPASS: an effective method for the refinement of crystal structures containing disordered solvent regions journal March 1990
Calixarene-Derived Fluorescent Probes journal September 2007
Synthesis of Mono- O -alkylated Homooxacalix[3]arene and a Protection–Deprotection Strategy for Homooxacalix[3]arene journal December 2016
Novel Cavity Design Using Calix[ n ]arene Skeletons:  Toward Molecular Recognition and Metal Binding journal August 1997
Pyrene-Linked Triazole-Modified Homooxacalix[3]arene: A Unique C 3 Symmetry Ratiometric Fluorescent Chemosensor for Pb 2+ journal February 2011
Novel Fluorometric Sensing of Ammonium Ions by Pyrene Functionalized Homotrioxacalix[3]arenes journal January 1994
Generalized Gradient Approximation Made Simple [Phys. Rev. Lett. 77, 3865 (1996)] journal February 1997
Synthesis and inclusion properties of O-tris(benzyloxy)hexahomotrioxacalix[3]arenes journal August 2006
A Self-Assembled Homooxacalix[3]arene-based Dimeric Capsule Constructed by a Pd II −Pyridine Interaction Which Shows a Novel Chiral Twisting Motion in Response to Guest Inclusion journal May 2001
Quantum Mechanical Calculations of Conformationally Relevant1H and13C NMR Chemical Shifts of N-, O-, and S-Substituted Calixarene Systems journal August 2007
Exploitation of Na + -Selective Electrodes for Protein Solutions from Crown-Bridged Calix[4]quinones journal January 1996
Click synthesis of a quinoline-functionalized hexahomotrioxacalix[3]arene: A turn-on fluorescence chemosensor for Fe3+ journal January 2018
Ab initio effective core potentials for molecular calculations. Potentials for the transition metal atoms Sc to Hg journal January 1985
Synthesis and evaluation of a novel fluorescent sensor based on hexahomotrioxacalix[3]arene for Zn 2+ and Cd 2+ journal August 2016
Artificial Organic Host Molecules for Anions journal August 1997
Ion and Molecular Recognition by Lower Rim 1,3-Di-conjugates of Calix[4]arene as Receptors journal August 2011
Synthesis, structure and inclusion properties of cone-tris{[(5′-methyl-2,2′-bipyridyl)-5-yl]oxycarbonylmethoxy}hexahomotrioxacalix[3]arene journal March 2011
Fifty years of oxacalix[3]arenes: A review journal January 2012
Complete asymmetric induction of supramolecular chirality in a hydrogen-bonded assembly journal April 1999
Heteroditopic receptors tris(2-pyridylamide) derivatives derived from hexahomotrioxacalix[3]arene triacetic acid journal September 2010
Ab initio effective core potentials for molecular calculations. Potentials for main group elements Na to Bi journal January 1985
Coumarin-Derived Cu 2+ -Selective Fluorescence Sensor: Synthesis, Mechanisms, and Applications in Living Cells journal February 2009
Anion Recognition and Sensing: The State of the Art and Future Perspectives journal January 2001
Calixarene-Based Molecules for Cation Recognition journal October 2002
Control of Structural Isomerism in Noncovalent Hydrogen-Bonded Assemblies Using Peripheral Chiral Information journal April 2000
Calixarene-Derived Fluorescent Probes journal December 2007
Recognition and binding of paraquat dichloride by cyclodextrin/calix[6]pyrrole binary host systems journal November 2002

Linked Research (2)

Figures / Tables (9)

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Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
hexahomotrioxacalix[3]arene
alkylammonium ions
metal ions
ditopic receptor
allosteric effects