Synthetic study demonstrates stabilization of diazaheptacene derivatives using bulky silylethynyl groups, indicating a strategy to prevent Diels-Alder dimerization.
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.
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Engelhart et al. (2014) studied this question.
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