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Title: Bipyrrole-Strapped Calix[4]pyrroles: Strong Anion Receptors That Extract the Sulfate Anion

Abstract

Cage-type calix[4]pyrroles 2 and 3 bearing two additional pyrrole groups on the strap have been synthesized. Compared with the parent calix[4]pyrrole (1), they were found to exhibit remarkably enhanced affinities for anions, including the sulfate anion (TBA+ salts), in organic media (CD2Cl2). This increase is ascribed to participation of the bipyrrole units in anion binding. Receptors 2 and 3 extract the hydrophilic sulfate anion (as the methyltrialkyl(C8-10)ammonium (A336+) salt)) from aqueous media into a chloroform phase with significantly improved efficiency (>10-fold relative to calix[4]pyrrole 1). These two receptors also solubilize into chloroform the otherwise insoluble sulfate salt, (TMA)2SO4 (tetramethylammonium sulfate).

Authors:
 [1];  [1];  [2];  [1];  [2];  [2];  [3]
  1. University of Texas at Austin
  2. ORNL
  3. University of Texas
Publication Date:
Research Org.:
Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States)
Sponsoring Org.:
USDOE Office of Science (SC)
OSTI Identifier:
1162081
DOE Contract Number:  
DE-AC05-00OR22725
Resource Type:
Journal Article
Journal Name:
Journal of the American Chemical Society
Additional Journal Information:
Journal Volume: 136; Journal Issue: 42; Journal ID: ISSN 0002--7863
Country of Publication:
United States
Language:
English

Citation Formats

Kim, Sung Kuk, Lee, Juhoon, Williams, Neil J, Lynch, Vincent M., Hay, Benjamin, Moyer, Bruce A, and Sessler, Jonathan L.. Bipyrrole-Strapped Calix[4]pyrroles: Strong Anion Receptors That Extract the Sulfate Anion. United States: N. p., 2014. Web. doi:10.1021/ja5086996.
Kim, Sung Kuk, Lee, Juhoon, Williams, Neil J, Lynch, Vincent M., Hay, Benjamin, Moyer, Bruce A, & Sessler, Jonathan L.. Bipyrrole-Strapped Calix[4]pyrroles: Strong Anion Receptors That Extract the Sulfate Anion. United States. https://doi.org/10.1021/ja5086996
Kim, Sung Kuk, Lee, Juhoon, Williams, Neil J, Lynch, Vincent M., Hay, Benjamin, Moyer, Bruce A, and Sessler, Jonathan L.. Wed . "Bipyrrole-Strapped Calix[4]pyrroles: Strong Anion Receptors That Extract the Sulfate Anion". United States. https://doi.org/10.1021/ja5086996.
@article{osti_1162081,
title = {Bipyrrole-Strapped Calix[4]pyrroles: Strong Anion Receptors That Extract the Sulfate Anion},
author = {Kim, Sung Kuk and Lee, Juhoon and Williams, Neil J and Lynch, Vincent M. and Hay, Benjamin and Moyer, Bruce A and Sessler, Jonathan L.},
abstractNote = {Cage-type calix[4]pyrroles 2 and 3 bearing two additional pyrrole groups on the strap have been synthesized. Compared with the parent calix[4]pyrrole (1), they were found to exhibit remarkably enhanced affinities for anions, including the sulfate anion (TBA+ salts), in organic media (CD2Cl2). This increase is ascribed to participation of the bipyrrole units in anion binding. Receptors 2 and 3 extract the hydrophilic sulfate anion (as the methyltrialkyl(C8-10)ammonium (A336+) salt)) from aqueous media into a chloroform phase with significantly improved efficiency (>10-fold relative to calix[4]pyrrole 1). These two receptors also solubilize into chloroform the otherwise insoluble sulfate salt, (TMA)2SO4 (tetramethylammonium sulfate).},
doi = {10.1021/ja5086996},
url = {https://www.osti.gov/biblio/1162081}, journal = {Journal of the American Chemical Society},
issn = {0002--7863},
number = 42,
volume = 136,
place = {United States},
year = {2014},
month = {1}
}