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

Xiaodong Chi | Zendy; Gretchen Marie Peters | Zendy; Forrest Hammel | Zendy; C. J. Brockman | Zendy; Jonathan L. Sessler | Zendy

Open Access

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

Author(s) -

Xiaodong Chi,

Gretchen Marie Peters,

Forrest Hammel,

C. J. Brockman,

Jonathan L. Sessler

Publication year - 2017

Publication title -

journal of the american chemical society

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 7.115

H-Index - 612

eISSN - 1520-5126

pISSN - 0002-7863

DOI - 10.1021/jacs.7b04529

Subject(s) - chemistry , anthracene , micelle , molecular recognition , amphiphile , aqueous solution , pyrrole , ion , extraction (chemistry) , self assembly , aqueous medium , molecule , inorganic chemistry , organic chemistry , copolymer , polymer

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 FeF 2 , receptor 1 self-assembles into multimicelles in aqueous media. This aggregation process is ascribed to a change in polarity from nonpolar 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 FeF 2 ion pairs from bulk aqueous solutions. The present work helps illustrate how molecular recognition and self-assembly may be used to control the chemistry of extractants at interfaces.

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