Pi‐Extended Diindole‐Fused Azapentacenone: Synthesis, Characterization, and Photophysical and Lithium‐Storage Properties

Abstract

Pi-extended polyaromatics tend to exhibit improved electronic properties with respect to the intrinsic structures. Herein, the rational design of a π-extended diindole-fused diazapentacenone (IP), with a nine-ring-fused core, obtained by applying an intramolecular Friedel-Crafts diacylation synthetic routine, is reported. The chemical structure, physical properties, and morphology of IP were fully characterized. Serving as an organic cathode material for a lithium-ion battery, the as-prepared nanorods of π-extended IP display higher conductivity and superior electrochemical performance than those of the naked diazapentacenone without diindole fusion.

Highly Efficient and Stable Perovskite Solar Cells Enabled by Low‐Cost Industrial Organic Pigment Coating

“…These characteristics afford QA impressive physicochemical properties, including high stabilities against light and heat (sublimation temperature >500 °C) and excellent charge carrier mobility (0.2 cm 2 V −1 s −1 ) in electronic devices [21, 24] . In addition to industrial colorant applications, QA has been explored for use in organic field‐effect transistors, [21] light‐emitting diodes, [25] photovoltaic devices, [26–28] as well as in carbon dioxide and lithium‐ion capture, because of its outstanding electrochemical properties [24, 29] …”

“…[21,24] In addition to industrial colorant applications,Q Ah as been explored for use in organic field-effect transistors, [21] lightemitting diodes, [25] photovoltaic devices, [26][27][28] as well as in carbon dioxide and lithium-ion capture,b ecause of its outstanding electrochemical properties. [24,29] Herein, we report the use of QA for surface passivation of halide perovskite thin films via af acile spin-coating-annealing process to achieve highly efficient and stable PSCs.A soluble derivative of QA, N,N-bis(tert-butyloxycarbonyl)quinacridone (TBOC-QA), was employed to prepare TBOC-QA covered halide perovskite (MAPbI 3 )t hin films by solution processing, which was readily converted to an insoluble QA passivation layer after thermal annealing. Experimental and computational results suggest that QA can effectively passivate the halide perovskite thin films by reducing the defects through Lewis base-acid interactions between the C = Ogroups and antisite Pb sites in MAPbI 3 and PbI 2 .Q Aw as also found to improve the electrical contact between the perovskite and hole-transporting layers.T he cascading high occupied molecular orbital (HOMO) energy levels promote charge extraction and enhance PCEs.M oreover, the insoluble QA coating significantly increased the water contact angle of surface passivated halide perovskite thin films and greatly improved the long-term stability of PSCs.…”

Recent Advances in Heterocyclic Nanographenes and Other Polycyclic Heteroaromatic Compounds

“…In 2016, Huang, Yu, and Xie et al reported the preparation of the diindole-fused azapentacenone 272.3 using an improved procedure ( Scheme 272 ). 511 First, the commercially available 272.1 was subjected to the copper(I)-catalyzed Ullmann-type reaction with carbazole to give 272.2 in 76% yield. Afterward, 272.2 was hydrolyzed and activated by SOCl 2 .…”

Diels–Alder Cycloaddition to the Bay Region of Perylene and Its Derivatives as an Attractive Strategy for PAH Core Expansion: Theoretical and Practical Aspects

“…A great deal of research interest has been shown in PAHs (polycyclic aromatic hydrocarbons), which include compounds such as perylene, benzoperylene, coronenes, ovalenes, naphthoperylene, bisanthene, and other hydrocarbons based on the perylene structure, and various functionalized derivatives of the aforementioned molecules. Compounds of this type are of particular interest in such areas as chemistry and material science and in modern technology [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16][17][18][19][20]. It is worth mentioning that perylene itself has persisted as an important unit in organic material chemistry, especially in dye chemistry, for over a century [21][22][23][24][25].…”