A Naphtho-Fused Double [7]Helicene from a Maleate-Bridged Chrysene Trimer
Marli Ferreira1,2, Guillaume Naulet3, Hugo Gallardo2
1Centre de Recherche Paul Pascal, CNRS, 115, av. Schweitzer, 33600, Pessac, France.
Abstract:
Perkin condensation of chrysenyl-6-acetic acid with chrysenylene-6,12-diglyoxylic acid followed by in situ esterification gives a bismaleate, whose conjugated stilbene moieties are efficiently shielded against intermolecular condensations and undergo iodine-catalyzed oxidative photocyclization in toluene without the need for high dilution. The concentration is limited by the low solubility of the flexible bismaleate at room temperature. The so-obtained double [7]helicene crystallizes in a nonchiral meso form. It is notably more soluble than its flexible precursor because it cannot fold to optimize π-π stacking.
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