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:
-
- Saga Univ., Saga (Japan). Dept. of Applied Chemistry, Faculty of Science and Engineering
- Memorial Univ. of Newfoundland, St. John’s, NL (United States). Dept. of Chemistry
- Guizhou Univ., Guiyang (China). Key Lab. of Macrocyclic and Supramolecular Chemistry of Guizhou Province
- Loughborough Univ., Loughborough (United States). Chemistry Dept.
- Univ. of Hull, Hull, Yorkshire (United States). School of Mathematics and Physical Sciences
- 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)
- 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 = {2018},
month = {2}
}
Web of Science
Figures / Tables:

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