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Dicarboxylic Acid Separation by Dynamic and Size‐Matched Recognition in Solution and in the Solid State
Author(s) -
Kumar Vijith,
Pilati Tullio,
Terraneo Giancarlo,
Ciancaleoni Gianluca,
Macchioni Alceo,
Resnati Giuseppe,
Metrangolo Pierangelo
Publication year - 2018
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201711822
Subject(s) - dication , hydrogen bond , chemistry , intermolecular force , solubility , alkyl , salt (chemistry) , molecular recognition , carboxylic acid , polymer chemistry , ion , organic chemistry , molecule
Bis(trimethylammonium) alkane diiodides dynamically encapsulate dicarboxylic acids through intermolecular hydrogen bonds between the I − anions of the hosts and the carboxylic OH groups of the guests. A selective recognition is realized when the size of the I − ⋅⋅⋅HOOC(CH 2 /CF 2 ) n COOH⋅⋅⋅I − superanion matches the dication alkyl chain length. Dynamic recognition is also demonstrated in solution, where the presence of the size‐matching organic salt boosts the acid solubility profile, thus allowing efficient mixture separation.