Journal article
Total Syntheses Supramolecular Style: Solid-State Construction of [2.2]Cyclophanes with Modular Control of Stereochemistry
Crystal growth & design, Vol.20(4), pp.2584-2589
04/01/2020
DOI: 10.1021/acs.cgd.9b01712
Abstract
A series of templated solid-state reactions are used to construct the ‘bent’ isomer of the [2.2]cyclophane family of molecules. Small-molecule hydrogen-bond-donor templates based on resorcinol complete the supramolecular construction of ortho-, meta-, and para-[2.2]cyclophanes in the solid state. The family of exo,exo-dicyclobutyl[2.2]cyclophanes forms regiospecifically in up to quantitative yields. The confines of the organic solid state and the modular nature of the template approach allow for the generation of a less stable exo,endo-[2.2]metacyclophane by simply changing the template to enforce a concomitant change in self-assembly. Our results demonstrate the first completed solid-state construction of each member of the family of [2.2]cyclophanes.
Details
- Title: Subtitle
- Total Syntheses Supramolecular Style: Solid-State Construction of [2.2]Cyclophanes with Modular Control of Stereochemistry
- Creators
- Tomislav Friščić - McGill UniversityElizabeth Elacqua - Department of Chemistry and Materials Research InstituteSaikat Dutta - Department of ChemistryShalisa M Oburn - Department of ChemistryLeonard R MacGillivray - Department of Chemistry
- Resource Type
- Journal article
- Publication Details
- Crystal growth & design, Vol.20(4), pp.2584-2589
- Publisher
- American Chemical Society
- DOI
- 10.1021/acs.cgd.9b01712
- ISSN
- 1528-7483
- eISSN
- 1528-7505
- Grant note
- DOI: 10.13039/100000078, name: Division of Materials Research, award: DMR-1708673
- Language
- English
- Date published
- 04/01/2020
- Academic Unit
- Pharmaceutical Sciences and Experimental Therapeutics; Chemistry
- Record Identifier
- 9984216709902771
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