Novel electroluminescent donor–acceptors based on dibenzo[a,c]phenazine as hole-transporting materials for organic electronics

2017 ◽  
Vol 41 (2) ◽  
pp. 628-638 ◽  
Author(s):  
Azam M. Shaikh ◽  
Bharat K. Sharma ◽  
Sajeev Chacko ◽  
Rajesh M. Kamble
Keyword(s):  
Organic Electronics ◽  
Amination Reaction ◽  
Hole Transporting ◽  
Palladium Catalyzed ◽  
Green Fluorescent ◽  
Hole Transporting Materials

Novel yellow-green fluorescent 3,6,11-trisubstitued-dibenzo[a,c]phenazine derivatives were synthesized via a Buchwald–Hartwig palladium-catalyzed C–N amination reaction for the hole-transporting materials.

Effects of meso-diarylamino group of porphyrins on optical and electrochemical properties

2020 ◽  
Vol 24 (01n03) ◽  
pp. 67-74 ◽  
Author(s):  
Tomohiro Higashino ◽  
Yamato Fujimori ◽  
Issei Nishimura ◽  
Hiroshi Imahori
Keyword(s):  
Functional Materials ◽  
Oxidation Potential ◽  
Electron Donors ◽  
Charge Transfer Complexes ◽  
Oxidative Amination ◽  
Amination Reaction ◽  
Hole Transporting ◽  
Porphyrin Core ◽  
Electron Donating Groups ◽  
Hole Transporting Materials

Introduction of an electron-donating meso-diarylamino group into a porphyrin core affords its broadened and red-shifted absorption and raises the HOMO level of the porphyrin. In this regard, porphyrins with multiple meso-diarylamino groups are expected to show unique optical and electrochemcial properties depending on the number of the meso-diarylamino groups. Herein, we report a series of porphyrins with a different number of the meso-diarylamino groups. They were prepared by the iodine(III)-mediated oxidative amination reaction of the corresponding meso-free porphyrins. With increasing the number of the meso-diarylamino groups, both red shifts and broadening in the absorption and negative shifts in the oxidation potential were observed. Notably, the oxidation potential of the porphyrin with four meso-diarylamino groups is comparable to that of tetrathiafulvalene, which is one of representative electron donors, suggesting the potential utility of multiply meso-aminated porphyrins as hole-transporting materials and as electron donors forming charge-transfer complexes with electron acceptors. We believe that this study sheds light on porphyrins with multiple electron-donating groups as organic functional materials.

The larger N-heteroacenes

2010 ◽  
Vol 82 (4) ◽  
pp. 953-968 ◽  
Author(s):  
Uwe H. F. Bunz
Keyword(s):  
Organic Chemistry ◽  
Optical Properties ◽  
Solid State ◽  
Organic Electronics ◽  
Literature Overview ◽  
Hole Transporting ◽  
Nitrogen Ring ◽  
Hole Transporting Materials ◽  
Molecular Skeleton

The history and development of pyrazine- and pyridine-type heteroacenes and their use in solid-state organic electronics are discussed and reviewed. The larger N-heteroacenes are potential electron- or hole-transporting materials and should therefore complement acenes in organic electronics. As they feature electronegative nitrogen ring atoms in their molecular skeleton, issues with oxidation should be less problematic when comparing them to the larger acenes such as pentacene. This paper covers the synthesis and the solid-state packing of larger (tetracene/pentacene-based) N,N-heterocylic acenes as well as the question of the interplay of aromaticity and antiaromaticity in the known larger N-heteroacenes and their N,N-dihydro-derivatives; also illuminated are their optical properties. A literature overview is provided. Keywords: acenes; alkynes; heterocycles; organic chemistry; organic electronics.

Anodic Oxidation of Novel Hole-Transporting Materials Derived from Tetraarylbenzidines. Electrochemical and Spectroscopic Characterization

2000 ◽  
Vol 65 (9) ◽  
pp. 1403-1418 ◽  
Author(s):  
René Fáber ◽  
G. Felix Mielke ◽  
Peter Rapta ◽  
Andrej Staško ◽  
Oskar Nuyken
Keyword(s):  
Anodic Oxidation ◽  
Molecular Design ◽  
Spectroscopic Characterization ◽  
Complex Compounds ◽  
Consecutive Reactions ◽  
Hole Transporting ◽  
Palladium Catalyzed ◽  
Model Substances ◽  
Hole Transporting Materials

Fluorenylidene-linked triarylamines, potential hole-transporting materials, have been prepared by the palladium-catalyzed Hartwig-Buchwald amination. Their redox and spectral properties were investigated in solution, applying cyclic voltammetry, UV-VIS and EPR spectroscopy, and in situ spectroelectrochemical measurements. N,N,N',N'-Tetraphenylbenzidine (1), N,N'-di(1-naphthyl)-N,N'-diphenylbenzidine (2), and triphenylamine (3) served as model substances in the study of the synthesized complex compounds 4 and 5. In structure 4, two triphenylamine centres are linked with a non-conjugated fluorene bridge; in structure 5, two tetraarylbenzidine skeletons with two nitrogens are linked with a conjugated biphenyl-bridge system. In addition, structure 5 contains a non-conjugated fluorene bridge. The presence of the fluorene moiety in the molecular design has a significant influence on the investigated properties of the new materials. In the anodic oxidation of the tetraarylbenzidine-type compounds (1, 2, and 5), two well-defined reversible oxidation peaks were observed. However, the oxidation of the triphenylamine-type structures (3 and 4) is more complex, due to fast consecutive reactions. The dimer-like structures (4 and 5) are characterized by two independent oxidation centres that are simultaneously oxidized at approximately the same potentials. This was confirmed by quantitative cyclovoltammetric as well as UV-VIS investigations.

scholarly journals Functional Pyrene–Pyridine-Integrated Hole-Transporting Materials for Solution-Processed OLEDs with Reduced Efficiency Roll-Off

ACS Omega ◽  
2021 ◽  
Author(s):  
Krishan Kumar ◽  
Kiran Kishore Kesavan ◽  
Diksha Thakur ◽  
Subrata Banik ◽  
Jayachandran Jayakumar ◽  
...  
Keyword(s):  
Solution Processed ◽  
Hole Transporting ◽  
Hole Transporting Materials

[2.2]Paracyclophane-based hole-transporting materials for perovskite solar cells

2021 ◽  
Vol 491 ◽  
pp. 229543
Author(s):  
Yin-Sheng Lin ◽  
Hsin Li ◽  
Wen-Sheng Yu ◽  
Szu-Tan Wang ◽  
Yi-Min Chang ◽  
...  
Keyword(s):  
Solar Cells ◽  
Perovskite Solar Cells ◽  
Hole Transporting ◽  
Hole Transporting Materials

Stable Perovskite Solar Cells Using Molecularly Engineered Functionalized Oligothiophenes as Low‐Cost Hole‐Transporting Materials

Small ◽  
2021 ◽  
pp. 2100783
Author(s):  
Vellaichamy Joseph ◽  
Albertus Adrian Sutanto ◽  
Cansu Igci ◽  
Olga A. Syzgantseva ◽  
Vygintas Jankauskas ◽  
...  
Keyword(s):  
Solar Cells ◽  
Low Cost ◽  
Perovskite Solar Cells ◽  
Hole Transporting ◽  
Hole Transporting Materials
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