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Title: Molecular Recognition Under Interfacial Conditions: Calix[4]pyrrole-Based Cross-linkable Micelles for Ion Pair Extraction

Abstract

An anthracene-functionalized, long-tailed calix[4]pyrrole 1, containing both an anion-recognition site and cation-recognition functionality, has been synthesized and fully characterized. Upon ion-pair complexation with FeF2, receptor 1 self-assembles into multi-micelles in aqueous media. This aggregation process is ascribed to a change in polarity from non-polar to amphiphilic induced upon concurrent anion and cation complexation and permits molecular recognition-based control over chemical morphology under interfacial conditions. Photoirradiation of the micelles serves to cross-link the anthracene units thus stabilizing the aggregates. The combination of ion pair recognition, micelle formation, and cross-linking can be used to extract FeF2 ion pairs from bulk aqueous solutions. In conclusion, the present work helps illustrate how molecular recognition and self-assembly may be used to control the chemistry of extractants at interfaces.

Authors:
 [1];  [1];  [1];  [1]; ORCiD logo [2]
  1. Univ. of Texas, Austin, TX (United States)
  2. Univ. of Texas, Austin, TX (United States); Shanghai Univ. (China)
Publication Date:
Research Org.:
Univ. of Texas, Austin, TX (United States)
Sponsoring Org.:
USDOE Office of Science (SC), Basic Energy Sciences (BES)
OSTI Identifier:
1735616
Grant/Contract Number:  
FG02-01ER15186
Resource Type:
Accepted Manuscript
Journal Name:
Journal of the American Chemical Society
Additional Journal Information:
Journal Volume: 139; Journal Issue: 27; Journal ID: ISSN 0002-7863
Publisher:
American Chemical Society (ACS)
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; Anions; Complexation; Receptors; Ions; Micelles

Citation Formats

Chi, Xiaodong, Peters, Gretchen Marie, Hammel, Forrest, Brockman, Chandler, and Sessler, Jonathan L. Molecular Recognition Under Interfacial Conditions: Calix[4]pyrrole-Based Cross-linkable Micelles for Ion Pair Extraction. United States: N. p., 2017. Web. doi:10.1021/jacs.7b04529.
Chi, Xiaodong, Peters, Gretchen Marie, Hammel, Forrest, Brockman, Chandler, & Sessler, Jonathan L. Molecular Recognition Under Interfacial Conditions: Calix[4]pyrrole-Based Cross-linkable Micelles for Ion Pair Extraction. United States. https://doi.org/10.1021/jacs.7b04529
Chi, Xiaodong, Peters, Gretchen Marie, Hammel, Forrest, Brockman, Chandler, and Sessler, Jonathan L. Thu . "Molecular Recognition Under Interfacial Conditions: Calix[4]pyrrole-Based Cross-linkable Micelles for Ion Pair Extraction". United States. https://doi.org/10.1021/jacs.7b04529. https://www.osti.gov/servlets/purl/1735616.
@article{osti_1735616,
title = {Molecular Recognition Under Interfacial Conditions: Calix[4]pyrrole-Based Cross-linkable Micelles for Ion Pair Extraction},
author = {Chi, Xiaodong and Peters, Gretchen Marie and Hammel, Forrest and Brockman, Chandler and Sessler, Jonathan L.},
abstractNote = {An anthracene-functionalized, long-tailed calix[4]pyrrole 1, containing both an anion-recognition site and cation-recognition functionality, has been synthesized and fully characterized. Upon ion-pair complexation with FeF2, receptor 1 self-assembles into multi-micelles in aqueous media. This aggregation process is ascribed to a change in polarity from non-polar to amphiphilic induced upon concurrent anion and cation complexation and permits molecular recognition-based control over chemical morphology under interfacial conditions. Photoirradiation of the micelles serves to cross-link the anthracene units thus stabilizing the aggregates. The combination of ion pair recognition, micelle formation, and cross-linking can be used to extract FeF2 ion pairs from bulk aqueous solutions. In conclusion, the present work helps illustrate how molecular recognition and self-assembly may be used to control the chemistry of extractants at interfaces.},
doi = {10.1021/jacs.7b04529},
journal = {Journal of the American Chemical Society},
number = 27,
volume = 139,
place = {United States},
year = {Thu Jun 22 00:00:00 EDT 2017},
month = {Thu Jun 22 00:00:00 EDT 2017}
}

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