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Issue 84, 2017
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Non-planar oligoarylene macrocycles from biphenyl

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Saddle- and propeller-shaped macrocycles are obtained by fourfold Perkin condensations in transient high dilution of 4,4′-bis(phenylglyoxylic acid) with either 4,4′-bis(phenylacetic acid) or p-phenylenediacetic acid, followed by four-fold oxidative photocyclizations. In the saddle-shaped tetraphenanthrylene, the angle between opposite phenanthrene planes is close to the value of 90° of an ideal saddle. In the two helicene fragments of the propeller-shaped double [5]helicene, the geometry of unsubstituted [5]helicene is preserved without major macrocycle-induced distortions.

Graphical abstract: Non-planar oligoarylene macrocycles from biphenyl

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The article was received on 30 Aug 2017, accepted on 21 Sep 2017 and first published on 21 Sep 2017

Article type: Communication
DOI: 10.1039/C7CC06798D
Chem. Commun., 2017,53, 11540-11543

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    Non-planar oligoarylene macrocycles from biphenyl

    A. Robert, P. Dechambenoit, E. A. Hillard, H. Bock and F. Durola, Chem. Commun., 2017, 53, 11540
    DOI: 10.1039/C7CC06798D

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