11,16‐Di‐tert‐butyl‐9,18‐diphenylbenzo[kl]benzo[8,9]triphenyleno [2,3‐b]xanthene: Synthesis, Photophysics, Self‐Assembly and Electroluminescent Properties

Abstract

A highly thermally stable twistarene, namely 11, 16di-tert-butyl-9,18-diphenylbenzo[kl]benzo [8,9]triphenyleno [2,3-b]xanthene (BTX), has been synthesized via a simple reaction, and its structure was unambiguously determined by single crystal X-ray analysis with a twisted angle of 37.9°b etween plane C1-C2-C4 and plane C16-C17-C24. More interestingly, molecule BTX could self-assembly into nano-wires and nanospheres via simple reprecipitation, which were characterized by scanning electron microscope (SEM), UV-vis absorption and emission spectra. The fabricated electroluminescent devices based on BTX as active ingredient presented a maximum brightness of 4355 cd m À 2 (bias voltage at 9.0 V) with CIE coordinate of (0.14, 0.53). Scheme 1. Chemical structures of compounds TBH and BTX.substrate was put into the ultraviolet ozone instrument for surface treatment. After 30 min, the prepared PEDOT : PSS solution was rotated evenly on the surface of the substrate through spinning process, which was dried in an oven at 130°C for 15 min. BTX predissolved in chlorobenzene solution with various concentration (8 mg/mL, 10 mg/mL, 12 mg/mL, 14 mg/mL) were spin-coated on the substrate in nitrogen glove box, and then fade at 100°C for 10 min. Then, TPBi, LiF and Al were evaporated on the substrate in 6 × 10 À 4 Pa. The device performances (EL spectra, JÀ V curves, EQE values, and CIE coordinates) were recorded with a spectrophotometer (FLAM-ETVIS-NIR-ES of ocean optics) and a computer controlled Keithley 2400 Sourcemeter (America Photo Research), respectively.

Recent Advances in Heterocyclic Nanographenes and Other Polycyclic Heteroaromatic Compounds

“… Reagents and conditions: (a) 348 1-naphthol, PPh 3 , Cs 2 CO 3 , Pd(OAc) 2 , DMF, 140 °C, 24 h; (b) 349 catechol, NaH, NMP, 205 °C, 12 h; (c) 2-aminophenol, NaH, NMP, 205 °C, 12 h; (d) 350 K 2 CO 3 , DMF, 110 °C. …”

“…A pyran-containing system 174.2 was synthesized in 42% yield via a one-step Pd-catalyzed annulation between 174.1 and 1-naphthol (Scheme ). Under controlled conditions, 174.2 assembled into various morphologies (nanowires or nanospheres), as evidenced by SEM, UV–vis absorption, and emission data. The fabricated electroluminescent devices based on 174.2 had a maximum brightness of 4355 cd m –2 (bias voltage at 9.0 V) with CIE coordinates of (0.14, 0.53).…”

Repercussions of multi-electron uptake by a twistacene: a reduction-induced double dehydrogenative annulation

“…50,51 Twistacenes provide a sterically crowded π-scaffold where dehydrogenation and C-C bond formation can also occur. 42,43 While there are some reports on the electrochemical behaviour of twistacenes, 20,[52][53][54][55][56][57][58][59][60][61][62] the outcomes of chemical reduction of twistacenes have remained unexplored. To the best of our knowledge, no X-ray diffraction studies revealing structural consequences of electron addition to twistacenes or alkalimetal ion binding patterns to the twistacene anions have been reported.…”