6533b872fe1ef96bd12d43f0

RESEARCH PRODUCT

Further synthetic and structural investigations of new pre-organized picket porphyrins

Valérie Baveux-chambenoîtAmandine DidierBernard BoitrelPhilippe RichardChristian Ruzié

subject

010405 organic chemistryStereochemistryAromaticityGeneral ChemistryConjugated system010402 general chemistry01 natural sciencesPorphyrin[ CHIM ] Chemical Sciences0104 chemical scienceschemistry.chemical_compoundCrystallographychemistryNucleophile[CHIM] Chemical SciencesPeptide bond[CHIM]Chemical SciencesPicketingComputingMilieux_MISCELLANEOUS

description

The straightforward synthesis of three new picket porphyrins with a restrained conformation is described. These porphyrins have an unusual behavior due to the conjugated but still flexible nature of their pickets. The crystal structure of their common precusor is also reported and confirms the presumed geometry of this type of picket. Indeed, the latter one is formally obtained by the conjugation of two aromatic rings through an amide bond. Although the specific shape of the picket is expected to overcrowd the center of the porphyrin, it is shown that different types of nucleophilic reagents can add easily on these pickets.

https://hal-univ-rennes1.archives-ouvertes.fr/hal-01469262