A persistent diazaheptacene derivative

J Am Chem Soc. 2014 Oct 29;136(43):15166-9. doi: 10.1021/ja509723q. Epub 2014 Oct 15.

Abstract

We describe the synthesis of characterizable diazaheptacene derivatives. Diazaheptacenes need four silylethynyl protecting groups to be isolable. TIPS-ethynyl groups are not bulky enough to allow stabilization. Four Si(sec-Bu)3-ethynyl groups symmetrically attached to the acene core sufficiently protect the formed diazaheptacene from dimerization through Diels-Alder reaction. It was characterized by NMR and UV-vis spectroscopies and cyclic voltammetry.