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Encapsulation and Stabilization of Reactive Aromatic Diazonium Ions and the Tropylium Ion Within a Supramolecular Host
Author(s) -
Brumaghim Julia L.,
Michels Martin,
Pagliero Daniela,
Raymond Kenneth N.
Publication year - 2004
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200400533
Subject(s) - chemistry , supramolecular chemistry , reactivity (psychology) , molecule , ion , host–guest chemistry , polymer chemistry , encapsulation (networking) , supramolecular assembly , photochemistry , combinatorial chemistry , organic chemistry , computer network , computer science , medicine , alternative medicine , pathology
Supramolecular assemblies with internal cavities are being developed as nanoscale reaction vessels to protect or modify the reactivity of guest species through encapsulation. Diazonium cations and the tropylium cation were examined for their ability to encapsulate in the tetrahedral [Ga 4 L 6 ] 12− supramolecular assembly. The 4‐(diethylamino)benzenediazonium cation 1 readily formed a 1:1 host−guest complex with this assembly, and this encapsulation prevented 1 from reacting with 2,4‐pentanedione in D 2 O. The tropylium cation also formed a 1:1 host−guest complex with the [Ga 4 L 6 ] 12− assembly, greatly slowing its decomposition in D 2 O. Encapsulation in the protected environment of this host cavity alters the reactivity of these guest molecules, giving them greater stability. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)