Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 19, Issue 45, Pages 15120-15132Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201302452
Keywords
cross-conjugation; cross-coupling; macrocycles; radialenes; strained molecules
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Funding
- NSERC
- University of Erlangen-Nuremberg
- Deutsche Forschungsgemeinschaft [DFG SFB 953]
- Interdisciplinary Center for Molecular Materials (ICMM)
- Excellence Initiative
- US NSF [DMR-1205302, CHE-1124075]
- Robert A. Welch Foundation [AH-0033]
- Direct For Mathematical & Physical Scien
- Division Of Materials Research [1205302] Funding Source: National Science Foundation
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [1110967] Funding Source: National Science Foundation
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Versatile, iterative synthetic protocols to form expanded [n]radialenes have been developed (n=3 and 4), which allow for a variety of groups to be placed around the periphery of the macrocyclic framework. The successful use of the Sonogashira cross-coupling reaction to complete the final ring closure demonstrates the ability of this reaction to tolerate significant ring strain while producing moderate to excellent product yields. The resulting radialenes show good stability under normal laboratory conditions in spite of their strained, cyclic structures. The physical and electronic characteristics of the macrocycles have been documented by UV-visible spectroscopy, electrochemical methods, and X-ray crystallography (four derivatives), and these studies provide insight into the properties of these compounds as a function of pendent substitution in terms of conjugation and donor/acceptor functionalization.
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