Tetrakis(phenylethynyl)tetracene: A New π-Extended Rubrene Derivative.

Chemistry

Department of Applied Chemistry for Environment, Kwansei Gakuin University, 2-1 Gakuen, Sanda, 669-1337, Japan.

Published: September 2018

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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http://dx.doi.org/10.1002/chem.201803294DOI Listing

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