Dimesitylboryl‐Decorated Azaarene: Synthesis, Enhanced Stability and Optoelectronic Property

Abstract

The instability of large acenes and analogues usually limits their wide potentials in organic devices. Thus, effectively constructing large acenes or heteroacenes and examining their optoelectronic properties are of great interest. We herein describe the synthesis, optoelectronic behaviors and electroluminescent property of dimesitylboryl‐decorated azaarene 5 and its homologue 7. The former emits strong green fluorescence in non‐polar solvents but yellow light in polar solvents. The latter emits a blue light in various organic solvents. Moreover, their electrochemical behavior, photostability and electroluminescent property were further studied in a comparative manner, and the experimental findings suggest that the desired heteroarenes are appealing materials for fabricating electroluminescent devices.

Recent Advances in Heterocyclic Nanographenes and Other Polycyclic Heteroaromatic Compounds

“…The related bent twistacene 172.6a was synthesized from the respective dibromo precursor using a Cu-catalyzed amination reaction. 345 Compound 172.2 displayed blue fluorescence in DCM solution with maxima peaks at 455 and 475 nm and a quantum yield of 0.29, while 172.4 showed the bathochromic shift to 481 and 510 nm, resulting in green emission (Φ f = 0.32). Twistacenes 172.2 and 172.4 were tested as dopants in multilayered OLED devices and exhibited promising electroluminescent performance.…”

“… Reagents and conditions: (a) 344 P(OEt) 3 , o -DCB, 160 °C, 24 h; (b) aniline, Pd(OAc) 2 , PCy 3 , t -BuOK, toluene, reflux, 48 h; (c) 345 NaN 3 , CuI, N , N ′-dimethylethylenediamine, DMSO, 120 °C, 48 h; (d) (1) n -BuLi, THF, −78 °C, 2 h, (2) dimesitylboron fluoride, rt, 24 h. …”

“… The former reaction was regioselective, producing exclusively the angularly fused isomer 172.2 . The related bent twistacene 172.6a was synthesized from the respective dibromo precursor using a Cu-catalyzed amination reaction . Compound 172.2 displayed blue fluorescence in DCM solution with maxima peaks at 455 and 475 nm and a quantum yield of 0.29, while 172.4 showed the bathochromic shift to 481 and 510 nm, resulting in green emission (Φ f = 0.32).…”