Recent Progress in the Usage of Phenazinediamine and Its Analogues as Building Blocks to Construct Large N‐Heteroacenes

Abstract

Effectively increasing the length of N‐heteroacenes is highly desirable because such materials could have great potential applications in organic optoelectronics. In this review we summarize the recent progress in the construction of larger N‐heteroacenes based on the use of phenazinediamine and its analogues as building blocks to react with different kinds of ortho‐diketones (or tetraketones) or ortho‐dihalides through condensation or coupling reactions. In addition, the potential applications of the corresponding N‐heteroacenes are also presented.

Recent progress in pyrazinacenes containing nonbenzenoid rings: synthesis, properties and applications

“…1–3 For example, naphthalene-substituted anthracene derivatives have been well developed as suitable emitting materials for full-color organic electroluminescent devices with highly efficient and stable blue emission, 4 while a monocrystalline rubrene derivative displays a hole mobility as high as 40 cm 2 V −1 s −1 . 5 Currently, one of the main issues frustrating preparative chemists and materials scientists is their poor stability in air or under light, especially for those skeletons larger than pentacene, 6,7 which also limits their further applications in devices. Incorporating sp 2 nitrogen atoms into the backbone of acenes leads to so-called azaacenes, and has been reported to be an effective way to stabilize the scaffolds, 8 increase their electron affinity and improve electron transport properties, 9,10 as well as decrease the degree of synthetic difficulty by simple condensation reactions 11–13 or Pd-mediated coupling reactions, 14,15 etc.…”

A Potential Iterative Approach to 1,4‐Dihydro‐N‐Heteroacene Arrays

“…[19] Large N-heteroacenes have been made by various methods. Phenazinediamine and its analogues have been used as building blocks, [20] three-dimensional pyrene-fused N-heteroa-cenes were made by an iterative approach, [21] layered thiadiazoloquinoxaline-containing long pyrene-fused N-heteroacenes, [22] azaacenodibenzosuberones, [23] N-heteroacenes extended through a four-membered ring, [24] N-phenylated Nheteroacenes, [25] and novel types of sulfur-nitrogen-containing N-heteroacenes containing a high proportion of heteroatoms. [26] In the preliminary communication here, we report a synthesis and crystallographic structure for a non-planar mono-Nsubstituted dihydrophenazine and explain its significance.…”

Wavelength selective photoactivated autocatalytic oxidation of 5,12-dihydrobenzo[b]phenazine and its application in metal-free synthesis

“…1 Their utilization in chemical/bio sensing, 2 OLEDs (as the thermally activated delayed uorescence organic light emitters) 3 and the preparation of diradicals 4,5 has also been reported. These molecules can be prepared through the condensation of aromatic o-diamines with aromatic o-dihydroxyarenes or activated o-dihalides, 6 but the direct products of this condensation are dihydro N-heteroacene (H 2 -NHA) derivatives, which normally exhibit good chemical stability and are oen used to produce other H 2 -NHA derivatives. To get NHAs, oxidation of the H 2 -NHA is frequently needed (Scheme 1).…”