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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)
+ Show Author Affiliations

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: 3 works
Citation information provided by
Web of Science

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Novel Cavity Design Using Calix[ n ]arene Skeletons:  Toward Molecular Recognition and Metal Binding journal August 1997
Interlocked Macromolecules journal July 1999
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
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
Coumarin-Derived Cu 2+ -Selective Fluorescence Sensor: Synthesis, Mechanisms, and Applications in Living Cells journal February 2009
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 ion selectivity of conformers derived from hexahomotrioxacalix[3]arene journal October 1993
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
Pyrene-Linked Triazole-Modified Homooxacalix[3]arene: A Unique C 3 Symmetry Ratiometric Fluorescent Chemosensor for Pb 2+ journal February 2011
Recognition of 1,2-diazines by a bidentate Lewis acid journal January 1998
Ab initio effective core potentials for molecular calculations. Potentials for the transition metal atoms Sc to Hg journal January 1985
Ab initio effective core potentials for molecular calculations. Potentials for K to Au including the outermost core orbitals journal January 1985
Exploitation of Na + -Selective Electrodes for Protein Solutions from Crown-Bridged Calix[4]quinones journal January 1996
Synthesis and inclusion properties of O-tris(benzyloxy)hexahomotrioxacalix[3]arenes journal August 2006
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Linked Research (2)

Figures / Tables (9)

Scheme 1(p. 4)figure Scheme 1
Figure 1(p. 5)figure Figure 1
Figure 2(p. 6)figure Figure 2
Figure 3(p. 7)figure Figure 3
Table 1(p. 7)table Table 1
Table 2(p. 7)table Table 2
Figure 4(p. 8)figure Figure 4
Figure 5(p. 9)figure Figure 5
Figure 6(p. 9)figure Figure 6

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