14727-71-0Relevant articles and documents
Conjugated polymers constructed by a novel pyrene-fused polycyclic building block and their applications as organic electronic materials
Wen, Hui,Gong, Xiaohui,Jia, Zhenhong,Han, Pei,Lin, Baoping,Ye, Shanghui,Sun, Ying,Zhang, Xueqin,Yang, Hong
, p. 16 - 23 (2016)
A large fused polycyclic pyrene derivative with five-membered imidazole rings fused onto pyrene core, 5,11-Bis(5-Bromothiophene-2-yl)-4,10-dioctadecyl-4,10-dihydropyreno[4,5-d:9,10- d′]diimidazole (PBTI), was designed as a new building block for the conjugated polymers. Copolymers of this monomer with vinylene (P1) and thiophene (P2) were synthesized and their physical properties and performance in organic thin film transistors were investigated. Both polymers exhibited highly coplanar backbones, similar lowest unoccupied molecular orbital energy levels at -3.7 ev and the uniform delocalized highest occupied molecular orbital with deep-lying energy levels around -5.7 ev. X-ray diffraction and grazing-incident X-ray diffraction measurements demonstrated that P2 adopted a highly ordered structure, thus giving an enhanced hole mobility of 0.015 cm2 V-1 s-1 in organic thin film transistors.
Dicyanopyrazine-containing fused aromatic molecules: Potential n-type materials for use in optoelectronic devices
Li, Qing,Li, Jiuyan,Ren, Huicai,Gao, Zhanxian,Liu, Di
, p. 3325 - 3333 (2011)
Two dicyanopyrazine-containing aromatic compounds, pyrazino[2′, 3′:9,10]phenanthro[4,5-fgh]quinoxaline-5,6,12,13-tetracarbonitrile (PPQD) and pyrazino[2′,3′:9,10]phenanthro[4,5-fgh]quinoxaline-5,6,12,13- tetracarbonitrile,2,9-bis(1,1-dimethylethyl) (PPQB), which have remarkably high electron affinity and ionization potential, were synthesized and qualified as potential n-type materials for use in solar cells and organic light-emitting diodes.
Solution-processable small molecule semiconductors based on pyrene-fused bisimidazole and influence of alkyl side-chain on the charge transport
Wen, Hui,Gong, Xiaohui,Han, Pei,Lin, Baoping,Zhang, Lei,Ye, Shanghui,Sun, Ying,Zhang, Xueqin,Yang, Hong
, p. 69277 - 69281 (2016)
To explore the potential of pyrene-fused biimidazole as a building block for soluble small molecule semiconductors, we designed and synthesized PBI-L-Na and PBI-B-Na. Imidazole rings provided substitution positions for the solubilising groups at the K-region, however, DFT calculations revealed that the repulsive steric hindrance from the neighboring hydrogen atoms on pyrene forced alkyl side chains into a twisted conformation. Thus, side chains on this type of molecule exerted a prominent influence on the molecular packing and affected their optoelectronic properties intensively in the solid state. PBI-L-Na exhibited a more ordered packing of the large conjugated plane with a π-π stacking distance of 0.36 nm and showed a hole mobility up to 0.12 cm2 V-1 s-1. Bulkier branched chains provided better solubility but impeded molecular packing of PBI-B-Na, thus giving a hole mobility of 4.6 × 10-3 cm2 V-1 s-1.
An Environmentally Friendly and Flexible Aqueous Zinc Battery Using an Organic Cathode
Guo, Zhaowei,Ma, Yuanyuan,Dong, Xiaoli,Huang, Jianhang,Wang, Yonggang,Xia, Yongyao
, p. 11737 - 11741 (2018)
Rechargeable batteries have been used to power various electric devices and store energy from renewables, but their toxic components (namely, electrode materials, electrolyte, and separator) generally cause serious environment issues when disused. Such toxicity characteristic makes them difficult to power future wearable electronic devices. Now an environmentally friendly and highly safe rechargeable battery, based on a pyrene-4,5,9,10-tetraone (PTO) cathode and zinc anode in mild aqueous electrolyte is presented. The PTO-cathode shows a high specific capacity (336 mAh g?1) for Zn2+ storage with fast kinetics and high reversibility. Thus, the PTO//Zn full cell exhibits a high energy density (186.7 Wh kg?1), supercapacitor-like power behavior and long-term lifespan (over 1000 cycles). Moreover, a belt-shaped PTO//Zn battery with robust mechanical durability and remarkable flexibility is first fabricated to clarify its potential application in wearable electronic devices.
Confined Spaces in [n]Cyclo-2,7-pyrenylenes
Dumele, Oliver,Grabicki, Niklas,Nguyen, Khoa T. D.,Weidner, Steffen
, p. 14909 - 14914 (2021)
A set of strained aromatic macrocycles based on [n]cyclo-2,7-(4,5,9,10-tetrahydro)pyrenylenes is presented with size-dependent photophysical properties. The K-region of pyrene was functionalized with ethylene glycol groups to decorate the outer rim and thereby confine the space inside the macrocycle. This confined space is especially pronounced for n=5, which leads to an internal binding of up to 8.0×104 m?1 between the ether-decorated [5]cyclo-2,7-pyrenylene and shape-complementary crown ether–cation complexes. Both the ether-decorated [n]cyclo-pyrenylenes as well as one of their host–guest complexes have been structurally characterized by single-crystal X-ray analysis. In combination with computational methods the structural and thermodynamic reasons for the exceptionally strong binding have been elucidated. The presented rim confinement strategy makes cycloparaphenylenes an attractive supramolecular host family with a favorable, size-independent read-out signature and binding capabilities extending beyond fullerene guests.
Relationship Between Molecular Structure, Single crystal Packing and Self-Assembly Behavior: A Case Based on Pyrene Imide Derivatives
Chen, Jiawen,Chen, Wangqiao,Han, Hongjing,Li, Xiaojun,Qiu, Meizhen,Zhang, Qichun,Zhang, Shilong
supporting information, (2021/12/08)
Development of new n-type one-dimensional (1D) self-assembly nanostructure and a clear understanding of the relationship between molecular structure and self-assembly behavior are important prerequisites for further designing and optimizing organic optoelectronic nanodevice. In this article, a series of n-type organic semiconductor materials based on pyrene imide were successfully synthesized through [4+2] cycloaddition reactions and their preliminary optical and electrochemical properties were studied. The simulated HOMO-LUMO bandgaps via DFT tallied with the experimental data well. The self-assembly of these materials showed needle or fiber-like morphologies, indicating that different conjugation degree or alkyl group had significant influence on their self-assembly behaviors. Furthermore, the single-crystal packing for these molecules were analyzed and it was found out that the changes of conjugated backbone and functional group would affect certain crystal lattice parameter significantly, such as the intermolecular packing distance and crystal size etc, which would further result in different self-assembly morphology.
Organic compound, mixture and composition and application thereof
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Paragraph 0147-0150, (2021/06/02)
The invention relates to an organic compound, a mixture and a composition and an application thereof, and in particular, relates to an application in an organic light-emitting diode. The organic compound disclosed by the invention, represented by a general formula (1), has excellent hole transport property and stability, can be used as a hole injection layer material in an organic electroluminescent element, and can also be used as a dopant to be doped in a hole injection layer or a hole transport layer, so that low-voltage driving can be realized, the electroluminescent efficiency can also be improved, and the device life is prolonged.
