A Naphtho-Fused Double [7]Helicene from a Maleate-Bridged Chrysene Trimer
Dr. Marli Ferreira
Centre de Recherche Paul Pascal, CNRS, 115, av. Schweitzer, 33600 Pessac, France
Departamento de Química, Universidade Federal de Santa Catarina, CEP, 88040-900 Florianópolis, Santa Catarina, Brazil
Search for more papers by this authorGuillaume Naulet
Centre de Recherche Paul Pascal, Université de Bordeaux, 115, av. Schweitzer, 33600 Pessac, France
Search for more papers by this authorProf. Hugo Gallardo
Departamento de Química, Universidade Federal de Santa Catarina, CEP, 88040-900 Florianópolis, Santa Catarina, Brazil
Search for more papers by this authorDr. Pierre Dechambenoit
Centre de Recherche Paul Pascal, Université de Bordeaux, 115, av. Schweitzer, 33600 Pessac, France
Search for more papers by this authorCorresponding Author
Dr. Harald Bock
Centre de Recherche Paul Pascal, CNRS, 115, av. Schweitzer, 33600 Pessac, France
Search for more papers by this authorCorresponding Author
Dr. Fabien Durola
Centre de Recherche Paul Pascal, CNRS, 115, av. Schweitzer, 33600 Pessac, France
Search for more papers by this authorDr. Marli Ferreira
Centre de Recherche Paul Pascal, CNRS, 115, av. Schweitzer, 33600 Pessac, France
Departamento de Química, Universidade Federal de Santa Catarina, CEP, 88040-900 Florianópolis, Santa Catarina, Brazil
Search for more papers by this authorGuillaume Naulet
Centre de Recherche Paul Pascal, Université de Bordeaux, 115, av. Schweitzer, 33600 Pessac, France
Search for more papers by this authorProf. Hugo Gallardo
Departamento de Química, Universidade Federal de Santa Catarina, CEP, 88040-900 Florianópolis, Santa Catarina, Brazil
Search for more papers by this authorDr. Pierre Dechambenoit
Centre de Recherche Paul Pascal, Université de Bordeaux, 115, av. Schweitzer, 33600 Pessac, France
Search for more papers by this authorCorresponding Author
Dr. Harald Bock
Centre de Recherche Paul Pascal, CNRS, 115, av. Schweitzer, 33600 Pessac, France
Search for more papers by this authorCorresponding Author
Dr. Fabien Durola
Centre de Recherche Paul Pascal, CNRS, 115, av. Schweitzer, 33600 Pessac, France
Search for more papers by this authorGraphical Abstract
It takes only five consecutive steps from unsubstituted chrysene to obtain an all-kata-annulated arene tetracarboxylate, in which two heptahelicene segments are joined together. The bishelicene is formed in the achiral meso configuration, with the two helices having opposite pitches.
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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