Engineering solid-state morphologies in carbazole-ethynylene macrocycles

Aaron D. Finke, Dustin E. Gross, Amy Han, Jeffrey S. Moore

Research output: Contribution to journalArticlepeer-review

Abstract

We present a crystallographic study that systematically investigates the effects of the n-alkyl side-chain length on the crystal packing in shape-persistent macrocycles. The solid-state packing of carbazole-ethynylene- containing macrocycles is sensitive to the alkyl-chain length. In macrocycles containing n-alkyl side chains up to nine carbons in length, face-on aromatic π interactions predominate, while the addition of one carbon leads to a completely different packing arrangement. Macrocycles with C10 or C11 chains exhibit a novel packing motif wherein the alkyl chains intercalate between macrocycles, leading in one case to continuous solvent-filled channels. When crystals of the C10 macrocycle are bathed in solvent, the included molecules exchange with the external solvent, and the alkyl chain disorder changes in response to changes in the guest volume in order to retain crystallinity. Powder X-ray diffraction data indicate that alkyl-macrocycle interactions in the longer chains "emulate" the distances typical of face-to-face π interactions, leading to deceptive indicators of π stacking.

Original languageEnglish (US)
Pages (from-to)14063-14070
Number of pages8
JournalJournal of the American Chemical Society
Volume133
Issue number35
DOIs
StatePublished - Sep 7 2011

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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