SCHEDULED MAINTENANCE
Coronenes with push–pull geometries from macrocycle-forming Perkin condensations†
Abstract
Although the Perkin reaction has been successful in producing ester-substituted conjugated macrocycles with four or six building blocks, macrocycles composed of only two elements remained elusive until now. Through the development of a building block derived from phenanthrene with two glyoxylic acid substituents in a pincer-like arrangement, formation of a two-block macrocycle was induced when paired with a complementary phenylenediacetic acid unit. The addition of ether functions to the phenanthrene building block not only improved the yields, but led to macrocycles with push–pull geometries. Photocyclisation of the resulting cyclophanes efficiently yield tetra- and hexasubstituted coronenes.
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