skip to main content
OSTI.GOV title logo U.S. Department of Energy
Office of Scientific and Technical Information

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 C 3-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 C 3-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 C 3-symmetry was retained and higher complexation selectivity for n-BuNH 3 + versus t-BuNH 3 + 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-BuNH 3 + 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 Lab. (LBNL), Berkeley, CA (United States)
Sponsoring Org.:
USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22)
OSTI Identifier:
1434008
Grant/Contract Number:  
AC02-05CH11231
Resource Type:
Journal Article: 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. doi: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. doi: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},
issn = {1420-3049},
number = 2,
volume = 23,
place = {United States},
year = {2018},
month = {2}
}

Journal Article:
Free Publicly Available Full Text
Publisher's Version of Record

Save / Share:

Works referenced in this record:

Generalized Gradient Approximation Made Simple
journal, October 1996

  • Perdew, John P.; Burke, Kieron; Ernzerhof, Matthias
  • Physical Review Letters, Vol. 77, Issue 18, p. 3865-3868
  • DOI: 10.1103/PhysRevLett.77.3865

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

A Stepwise Huisgen Cycloaddition Process: Copper(I)-Catalyzed Regioselective �Ligation� of Azides and Terminal Alkynes
journal, July 2002


Thiacalixarenes
journal, December 2006

  • Morohashi, Naoya; Narumi, Fumitaka; Iki, Nobuhiko
  • Chemical Reviews, Vol. 106, Issue 12, p. 5291-5316
  • DOI: 10.1021/cr050565j