Equilibrating dynamic [2]rotaxanes

Philip C. Haussmann, Saeed I. Khan, J. Fraser Stoddart*

*Corresponding author for this work

Research output: Contribution to journalArticle

45 Scopus citations

Abstract

(Figure Presented) Upon mixing and dehydration, 2,6-diformylpyridine and 2,2′-oxybis(ethylamine) form a dynamic combinatorial library of at least nine members. Through hydrogen bonding and other intermolecular interactions, templating dumbbell molecules select one macrocyclic member of the library, at the expense of all the others, to create [2]rotaxanes. These rotaxanes, however, retain the dynamic character of the library, since a diformylpyridine analogue can exchange with the macrocyclic component in solution. In addition, crystallization of the mixture surprisingly furnishes only the [24]crown-8-like macrocycle on its own - evidence of a kinetic selection process occurring between phase transitions.

Original languageEnglish (US)
Pages (from-to)6708-6713
Number of pages6
JournalJournal of Organic Chemistry
Volume72
Issue number18
DOIs
StatePublished - Aug 31 2007

ASJC Scopus subject areas

  • Organic Chemistry

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