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

TitleSynthesis, structure, and computational studies of soluble conjugated multidentate macrocycles
Publication TypeJournal Article
Year of Publication2005
AuthorsGallant, AJ, Hui, JK-H, Zahariev, FE, Wang*, YA, MacLachlan*, MJ
JournalJ. Org. Chem.
Volume70
Pagination7936-7946
Date PublishedSep
Type of ArticleArticle
ISBN Number0022-3263
KeywordsCHEMISTRY, CRYSTAL-STRUCTURE, cyclodextrin, LIGANDS, LIQUID-CRYSTAL, METAL-COMPLEXES, porphyrins, RECEPTORS, SCHIFF-BASE MACROCYCLES, SHAPE-PERSISTENT MACROCYCLES, supramolecular
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 dibydroxydiiminobenzene 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.

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