Full Characterization and Photoelectrochemical Behavior of Pyrene‐fused Octaazadecacene and Tetraazaoctacene

Abstract

The preparation of large azaacenes is very important because of their great potential in organic electronics. In this report, we successfully synthesized and fully characterized two stable pyrene-fused large azaacenes: octaazadecacene and tetraazaoctacene through employing a relatively moderate aromatic unit pyrene as imbedded species in the backbone of azaacenes to ensure large conjugation and stability. The photoelectrochemical (PEC) studies indicate that both azaacenes display n-type semiconductor behavior.

Nonvolatile Tri‐State Resistive Memory Behavior of a Stable Pyrene‐Fused N‐Heteroacene with Ten Linearly‐Annulated Rings

“…In solution, compound 1 exhibits four absorption bands in the visible region ( λ max ) at 394, 522, 547 and 685 nm, together with one vibronic shoulder peak at 593 nm. Compared with another ten‐ring fused N‐heteroacene (OADA) reported earlier by our group, a new broad absorption band around 685 nm appears, which could attribute to the unique intramolecular charge transfer (ICT) between thiophene units and two linearly annulated acceptors. In film state, compound 1 displays a bathochromic shift for its ICT electronic absorbance.…”

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

“…It is well known that inserting moderating aromatic pyrene units into the frameworks of azaacenes might not only enhance the lengths of the azaacenes, but might also increase their stabilities and solubilities . In 2016 we successfully prepared the pyrene‐containing octazadecacene 46 (Scheme ) by performing a condensation between phenazinediamine 6 and substituted pyrenetetraone 18 . The photoelectrochemical behavior of 46 featured a repeatable anodic photocurrent, suggesting that 46 is an n‐type semiconductor (Figure ).…”

“…The flat‐band potential of 46 is indicated by the intercept of the dashed lines. Reprinted, with permission, from ref . Copyright 2015, WILEY‐VCH.…”

Pyrene-fused Acenes and Azaacenes: Synthesis and Applications

“…Recently, octazaacene with a pyrene unit in the center was synthesized and the as‐prepared compound showed high solubility, making device preparation convenient 49. The longer azaacenes would be easily obtained with longer diamines such as 36 and 37 ; tentazaacenes with pyrene units in the center have been synthesized (Scheme ) and both of them show photoactivity in photoelectrochemical cells50 (Figure ).…”