Synthesis of Hexaazatruxenes by Consecutive N−H/C−H Coupling Using a Hypervalent Iodine Reagent and Evaluation of Their Photophysical Properties

Abstract

Truxene is a C 3 -symmetric compound with characteristic photophysical properties, and it has great potential as a light-emitting material and building block. In this study, we demonstrate the synthesis of hexaazatruxenes using a two-step protocol. First, the hexaazatruxene precursors were prepared through the Buchwald-Hartwig amination of 1,3,5-tribromobenzene with commercially available or easily prepared amino-pyridine derivatives. Then, hexaazatruxenes were synthesized through consecutive NÀ H/CÀ H coupling using a hypervalent iodine reagent. To the best of our knowledge, this is the first report on the synthesis of truxenes containing more than three heteroatoms in the main skeleton.

An alternative approach to triazatruxene synthesis and derivatization to a boron difluoride complex

“…9 A recent example is hexaazatruxene, which is synthesized by the consecutive N-H/C-H coupling using iodobenzene diacetate as an oxidant. 10 Thus, with an appropriate precursor in hand, it is feasible to access 5,10,15-triazatruxene via the intramolecular cyclization strategy.…”