Journal article
Effect of remote substituents on solid state packing interactions in macrocyclic crownophanes derived from 1,3,5-triaroylbenzenes
Journal of Inclusion Phenomena and Macrocyclic Chemistry, Vol.62(1-2), pp.105-110
04/22/2008
DOI: 10.1007/s10847-008-9444-2
Abstract
A series of four structurally related crownophanes has been prepared and characterized by X-ray crystallography. The crownophanes are based upon a 1,3,5-triaroylbenzene framework and were synthesized via enaminone/alkyne cyclotrimerization. The crownophanes differ in the identity of a peripheral substituent attached to a remote arene ring that is not part of the cyclophane macrocycle. Solid state structural characterization reveals that crownophanes with remote phenyl and phenol substituents self-assemble to form centrosymmetric dimers. Incorporation of remote alkoxy groups (methoxy or ethoxy) disrupts dimerization and leads to catameric networks. Each crownophane crystallized as an inclusion complex or a hydrate and, in one instance, water was found to occupy the macrocyclic cavity.
Details
- Title: Subtitle
- Effect of remote substituents on solid state packing interactions in macrocyclic crownophanes derived from 1,3,5-triaroylbenzenes
- Creators
- F. Christopher Pigge - Department of Chemistry and Biochemistry, University of Missouri – St. Louis, Department of Chemistry, University of IowaAngela V Schmitt - Department of Chemistry and Biochemistry, University of Missouri – St. LouisNigam P Rath - Department of Chemistry and Biochemistry, University of Missouri – St. Louis
- Resource Type
- Journal article
- Publication Details
- Journal of Inclusion Phenomena and Macrocyclic Chemistry, Vol.62(1-2), pp.105-110
- Publisher
- Springer Netherlands
- DOI
- 10.1007/s10847-008-9444-2
- ISSN
- 0923-0750
- eISSN
- 1573-1111
- Language
- English
- Date published
- 04/22/2008
- Academic Unit
- Radiology; Chemistry
- Record Identifier
- 9984216608202771
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