Synthesis and Properties of anti/syn-Regioisomeric Mixtures of Alkyl-Substituted Tetracenes

Abstract

We prepared anti/syn-regioisomeric mixtures of alkyl-substituted tetracenes via Diels-Alder reaction between asymmetric furans and 2,6-naphthodiyne synthon.The solid-state color of the mixtures changed before and after recrystallization from Et 2 O, suggesting a difference in the molecular arrangements dependent on the different alkyl substituents as well as the change in the distribution of the anti/syn regioisomers after recrystallization.Slow evaporation of the recrystallized mixtures produced single crystals suitable for X-ray analysis, which revealed that the anti regioisomer was isolated.