Synthesis, structure, and computational studies of soluble conjugated multidentate macrocycles

Amanda J. Gallant, Joseph K.H. Hui, Federico E. Zahariev, Yan Alexander Wang, Mark J. MacLachlan

Research output: Contribution to journalArticlepeer-review

82 Citations (Scopus)

Abstract

Conjugated, shape-persistent macrocycles based on [3 + 3] Schiff-base condensation are of interest for supramolecular materials. In an effort to develop new discotic liquid crystals based on these compounds, a series of macrocycles with peripheral alkoxy groups of varying length have been prepared. The synthesis and mechanism of formation have been probed by isolation of oligomeric intermediates. A single-crystal X-ray diffraction study of one macrocycle revealed a nonplanar, strongly hydrogen-bonded structure. To our surprise, even with very long substituents, the macrocycles were not liquid crystalline. This has been rationalized by ab initio calculations that indicate the macrocycles are undergoing rotation of the dihydroxydiiminobenzene rings that may not allow a stable discotic liquid crystalline phase. These results provide new insight into the formation and properties of these large macrocycles and may provide guidance to developing stable liquid crystalline materials in the future.

Original languageEnglish
Pages (from-to)7936-7946
Number of pages11
JournalJournal of Organic Chemistry
Volume70
Issue number20
DOIs
Publication statusPublished - Sep 20 2005
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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