Trapping of bulky guests inside dimeric molecular capsules formed by a deep-cavity cavitand

Yanhua Qiu, Song Yi, Angel E. Kaifer

Research output: Contribution to journalArticle

7 Scopus citations

Abstract

The inclusion of three bulky guests, adamantyl(ferrocenylmethyl)amine (2), adamantylferrocenecarboxylamide (3), and 1,1′-bis(adamantylaminomethyl) ferrocene (4), inside dimeric molecular capsules formed by an octaacid deep-cavity cavitand (1) was investigated using 1H NMR spectroscopy and voltammetric techniques. Guests 2 and 3 were encapsulated inside 1 2 assemblies, as evidenced by 1H NMR spectroscopic data. Although both guests are electroactive, the supramolecular complexes 2@1 2 and 3@1 2 showed no voltammetric current responses in the potential window corresponding to the electrochemical oxidation of their ferrocenyl groups. In contrast, each of the adamantyl ends of compound 4 is bound by the cavitand 1, but the central ferrocene residue was not fully encapsulated in this supramolecular assembly and the voltammetric behavior of 4•1 2 was clearly detected. In marked contrast with the experimental results obtained with guests 2 and 3, we could not obtain any evidence for the simultaneous encapsulation of free ferrocene and adamantane inside the 1 2 capsular assembly.

Original languageEnglish (US)
Pages (from-to)4622-4627
Number of pages6
JournalJournal of Organic Chemistry
Volume77
Issue number10
DOIs
StatePublished - May 18 2012

ASJC Scopus subject areas

  • Organic Chemistry

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