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Tetrakis(dimethoxyphenyl)adamantane (TDA) and Its Inclusion Complexes in the Crystalline State: A Versatile Carrier for Small Molecules
Author(s) -
Schwenger Alexander,
Frey Wolfgang,
Richert Clemens
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201406568
Subject(s) - adamantane , molecule , chemistry , crystal structure , nitromethane , crystallography , context (archaeology) , crystal engineering , solid state , polymorphism (computer science) , benzene , stereochemistry , organic chemistry , supramolecular chemistry , paleontology , biochemistry , gene , genotype , biology
Molecular storage solutions for incorporating small molecules in crystalline matrices are of interest in the context of structure elucidation, decontamination, and slow release of active ingredients. Here we report the syntheses of 1,3,5,7‐tetrakis(2,4‐dimethoxyphenyl)adamantane, 1,3,5,7‐tetrakis(4‐methoxyphenyl)adamantane, 1,3,5,7‐tetrakis(4‐methoxy‐2‐methylphenyl)adamantane, and 1,3,5,7‐tetrakis(4‐methoxy‐2‐ethylphenyl)adamantane, together with their X‐ray crystal structures. All four compounds crystallize readily. Only the octaether shows an unusual level of (pseudo)polymorphism in its crystalline state, combined with the ability to include a number of different small molecules in its crystal lattices. A total of 20 different inclusion complexes with guest molecules as different as ethanol or trifluorobenzene were found. For nitromethane and benzene, schemes for uptake and release are presented.