An efficient synthetic route to 5,6,11,12-tetrakis(arylethynyl)tetracenes, new π-extended rubrene derivatives, was developed by means of [2+4] cycloaddition of dialkynylnaphthalyne and dialkynylisobenzofuran. Importantly, two alkynyl groups introduced into the aryne exerts a significant effect in lowering the LUMO energy, allowing practical access to sterically overcrowded polycyclic structures through an efficient HOMO-LUMO interaction. Study on the potential reactivity inherent in the peri-ethynyl-substituted tetracenes revealed several interesting reactivities. X-ray analysis of these new π-extended derivatives showed distorted structures to reduce steric repulsion due to the existence of the substituents at the peri-positions.
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