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

Abstract

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.

Authors:
 [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)
Publication Date:
Research Org.:
Lawrence Berkeley National Laboratory (LBNL), Berkeley, CA (United States)
Sponsoring Org.:
USDOE Office of Science (SC), Basic Energy Sciences (BES)
OSTI Identifier:
1434008
Grant/Contract Number:  
AC02-05CH11231
Resource Type:
Accepted Manuscript
Journal Name:
Molecules
Additional Journal Information:
Journal Volume: 23; Journal Issue: 2; Journal ID: ISSN 1420-3049
Publisher:
MDPI
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; hexahomotrioxacalix[3]arene; alkylammonium ions; metal ions; ditopic receptor; allosteric effects

Citation Formats

Jiang, Xue-Kai, Ikejiri, Yusuke, Wu, Chong, Rahman, Shofiur, Georghiou, Paris E., Zeng, Xi, Elsegood, Mark, Redshaw, Carl, Teat, Simon, and Yamato, Takehiko. A Hexahomotrioxacalix[3]arene-Based Ditopic Receptor for Alkylammonium Ions Controlled by Ag+ Ions. United States: N. p., 2018. Web. doi:10.3390/molecules23020467.
Jiang, Xue-Kai, Ikejiri, Yusuke, Wu, Chong, Rahman, Shofiur, Georghiou, Paris E., Zeng, Xi, Elsegood, Mark, Redshaw, Carl, Teat, Simon, & Yamato, Takehiko. A Hexahomotrioxacalix[3]arene-Based Ditopic Receptor for Alkylammonium Ions Controlled by Ag+ Ions. United States. https://doi.org/10.3390/molecules23020467
Jiang, Xue-Kai, Ikejiri, Yusuke, Wu, Chong, Rahman, Shofiur, Georghiou, Paris E., Zeng, Xi, Elsegood, Mark, Redshaw, Carl, Teat, Simon, and Yamato, Takehiko. Wed . "A Hexahomotrioxacalix[3]arene-Based Ditopic Receptor for Alkylammonium Ions Controlled by Ag+ Ions". United States. https://doi.org/10.3390/molecules23020467. https://www.osti.gov/servlets/purl/1434008.
@article{osti_1434008,
title = {A Hexahomotrioxacalix[3]arene-Based Ditopic Receptor for Alkylammonium Ions Controlled by Ag+ Ions},
author = {Jiang, Xue-Kai and Ikejiri, Yusuke and Wu, Chong and Rahman, Shofiur and Georghiou, Paris E. and Zeng, Xi and Elsegood, Mark and Redshaw, Carl and Teat, Simon and Yamato, Takehiko},
abstractNote = {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.},
doi = {10.3390/molecules23020467},
journal = {Molecules},
number = 2,
volume = 23,
place = {United States},
year = {Wed Feb 21 00:00:00 EST 2018},
month = {Wed Feb 21 00:00:00 EST 2018}
}

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Cited by: 2 works
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Figures / Tables:

Scheme 1 Scheme 1: Synthesis of receptor cone-1.

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Works referenced in this record:

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Ion and Molecular Recognition by Lower Rim 1,3-Di-conjugates of Calix[4]arene as Receptors
journal, August 2011

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  • Chemical Reviews, Vol. 111, Issue 8
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journal, May 2001

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Coumarin-Derived Cu 2+ -Selective Fluorescence Sensor: Synthesis, Mechanisms, and Applications in Living Cells
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Inclusion of [60]Fullerene in a Homooxacalix[3]arene-Based Dimeric Capsule Cross-Linked by a Pd II −Pyridine Interaction
journal, May 1999

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Synthesis and ion selectivity of conformers derived from hexahomotrioxacalix[3]arene
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Modification of the Upper Rim of Homooxacalix[3]arenes and Complexation between a Nitrohomooxacalix[3]arene Derivative and n -Hexylamine
journal, November 2002

  • Tsubaki, Kazunori; Otsubo, Tadamune; Morimoto, Tatsuya
  • The Journal of Organic Chemistry, Vol. 67, Issue 23
  • DOI: 10.1021/jo026152p

Optical Chemosensor for Ag + , Fe 3+ , and Cysteine: Information Processing at Molecular Level
journal, February 2011

  • Kumar, Manoj; Kumar, Rajesh; Bhalla, Vandana
  • Organic Letters, Vol. 13, Issue 3
  • DOI: 10.1021/ol102543e

Pyrene-Linked Triazole-Modified Homooxacalix[3]arene: A Unique C 3 Symmetry Ratiometric Fluorescent Chemosensor for Pb 2+
journal, February 2011

  • Ni, Xin-Long; Wang, Shi; Zeng, Xi
  • Organic Letters, Vol. 13, Issue 4
  • DOI: 10.1021/ol102914t

Recognition of 1,2-diazines by a bidentate Lewis acid
journal, January 1998

  • Gabbaï, François P.; Schier, Annette; Riede, Jürgen
  • Chemical Communications, Issue 8
  • DOI: 10.1039/a800413g

Ab initio effective core potentials for molecular calculations. Potentials for the transition metal atoms Sc to Hg
journal, January 1985

  • Hay, P. Jeffrey; Wadt, Willard R.
  • The Journal of Chemical Physics, Vol. 82, Issue 1
  • DOI: 10.1063/1.448799

Ab initio effective core potentials for molecular calculations. Potentials for K to Au including the outermost core orbitals
journal, January 1985

  • Hay, P. Jeffrey; Wadt, Willard R.
  • The Journal of Chemical Physics, Vol. 82, Issue 1, p. 299-310
  • DOI: 10.1063/1.448975

Exploitation of Na + -Selective Electrodes for Protein Solutions from Crown-Bridged Calix[4]quinones
journal, January 1996

  • Yamamoto, Hiromasa; Ueda, Keiko; Suenaga, Hikaru
  • Chemistry Letters, Vol. 25, Issue 1
  • DOI: 10.1246/cl.1996.39

Synthesis and inclusion properties of O-tris(benzyloxy)hexahomotrioxacalix[3]arenes
journal, August 2006

  • Yamato, Takehiko; Rahman, Shofiur; Kitajima, Fumika
  • Journal of Chemical Research, Vol. 2006, Issue 8
  • DOI: 10.3184/030823406778256351

Calixarene-Based Molecules for Cation Recognition
journal, October 2002


Fifty years of oxacalix[3]arenes: A review
journal, January 2012

  • Cottet, Kevin; Marcos, Paula M.; Cragg, Peter J.
  • Beilstein Journal of Organic Chemistry, Vol. 8
  • DOI: 10.3762/bjoc.8.22

Figures/Tables have been extracted from DOE-funded journal article accepted manuscripts.