27973-29-1Relevant articles and documents
Synthesis and electro-optical properties of carbazole-substituted pyrene derivatives
Jeong, Seonju,Park, Sung Hwan,Kim, Ki-Soo,Kwon, Younghwan,Ha, Ki-Ryong,Choi, Byeong-Dae,Han, Yoon Soo
, p. 4351 - 4356 (2011)
Mono and dicarbazole-substituted pyrene derivatives, 9H-carbazol-9-ylpyrene (MCzP) and 1,6-di(9H-carbazol-9-yl)pyrene (DCzP), with dual-purpose function as a blue emitting and charge transporting layer in organic light emitting diodes, were synthesized and characterized. These series of molecules consisted of an electron donating (D) carbazole and an electron accepting (A) pyrene in D-A and D-A-D shapes. Non-doped blue electroluminescent devices with the configurations of ITO (150 nm)/α-NPD (30 nm)/DCzP (40 nm)/LiF (1 nm)/Al (150 nm) (D1) and ITO (150 nm)/2-TNATA (15 nm)/α-NPD (20 nm)/DCzP (40 nm)/BCP (15 nm)/Alq3(10 nm)/LiF (1 nm)/Al (120 nm) (D2) were fabricated. D1 and D2 devices showed blue emission at 492 nm and 488 nm, and maximum luminance of 840 and 7560 cd/m2 obtained at 13 V and 15 V, respectively. 2011 American Scientific Publishers Copyright
A neutral state yellow to navy polymer electrochrome with pyrene scaffold
I?i-?zkut, Merve,?zta?, Zahide,Algi, Fatih,Cihaner, Atilla
, p. 1505 - 1511 (2011)
A new pyrene based soluble polymer, namely poly(3,3-didecyl-6-(1-(3,3- didecyl-3,4-dihydro-2H-thieno[3,4-b][1,4]dioxepin-6-yl)pyren-6-yl)-3, 4-dihydro-2H-thieno[3,4-b][1,4]dioxepine), P5, which is synthesized by both chemical and electrochemical methods, is highlighted. The polymer shows both electrochromic and fluorescent properties (the emission of yellow (545 nm) and yellowish green light (524 nm) in solid state and in THF solution, respectively). It is noteworthy that P5 has a specific optical band gap (2.2 eV) to reflect the yellow color in the neutral state. Furthermore, the optical and electrochemical features of the polymer were investigated.
Electrophilic Substitution of Monosubstituted Pyrenes
Minabe, Masahiro,Takeshige, Shouji,Soeda, Yuuji,Kimura,Takao,Tsubota, Motohiro
, p. 172 - 179 (1994)
Bromination and Friedel-Crafts acetylation of monosubstituted pyrenes were examined.Acetylation of 1-acetyl- and 1-ethylpyrene occurred at the 8-, 6-, or 3-position, but the reaction of 1-methoxypyrene afforded only the 8- and 6-acetyl derivatives.By acetylation, 4-acetylpyrene yielded the 1- and 6-acetyl compounds, and 4-ethylpyrene gave the 6- and 8-derivatives.Also 4-bromopyrene afforded the corresponding 8-, 6-, and 1-acetyl derivatives by the same reaction.Bromination of 1-ethyl- and 4-ethylpyrene yielded the 8- and 6-bromides, but the reaction of 1-nitro- and 1-bromopyrene took place at the 6-, 8-, of 3-position.The formation ratio of these regioisomers differs by the substituents.The regioselectivity on the acetylation accords in some degree with the prediction based on the 13C NMR chemical shift of each position.The relative rates of these electrophilic substitutions correlate to the substituent constant, ?+, of the substituent attached to the pyrene.
Pyrene derivatives with two types of substituents at positions 1, 3, 6, and 8-fad or necessity?
Zych, Dawid,Slodek, Aneta
, p. 24015 - 24024 (2019)
1,3,6,8-Tetrasubstituted pyrene derivatives with two types of substituents in an asymmetry or axial symmetry pattern have been prepared and characterized. To the best of our knowledge, these compounds are compared for the first time to their analogs containing the same substituent at all four positions, which explains the need for their synthesis. We present information on the chemistry of pyrenes, which are substituted in the non-K region, to help obtain the most efficient materials. Moreover, theoretical studies were extended to analogs which contain the first type of substituent at positions 1 and 3, whereas the second type of substituent is located at positions 6 and 8, for which the synthesis is nontrivial. The obtained data show which trend these kinds of molecules will follow.
A series of short axially symmetrically 1,3,6,8-tetrasubstituted pyrene-based green and blue emitters with 4-tert-butylphenyl and arylamine attachments
Zhang, Ran,Zhao, Yun,Zhang, Tengfei,Xu, Lu,Ni, Zhonghai
, p. 106 - 115 (2016)
A series of short axially symmetrically 1,3,6,8-tetrasubstituted pyrene-based derivatives (4a-4c) with two 4-tert-butylphenyl segments at 1,8-positions and two hole-transporting arylamine attachments at 3,6-sites of pyrene core were designed and synthesized based on stepwise synthetic strategy. These compounds were structurally characterized and their photoelectric properties were investigated by spectroscopy, electrochemical and theoretical studies. The results show that the incorporation of different arylamine units into pyrene core can tune the electronic structures of the compounds, and polysubstituted configuration of pyrene can effectively suppress the intermolecular π-π interactions and consequently leads to relatively high absolute fluorescence quantum efficiencies. These compounds exhibit high thermal stability and can form morphologically stable amorphous thin films with glass transition temperature in the range of 156-189 °C. Solution-processed non-doped green and blue organic light-emitting diodes with maximum luminance efficiencies 4.14 cd A-1 and 2.41 cd A-1 were achieved for 4b and 4c, respectively.
1,8-Substituted Pyrene Derivatives for High-Performance Organic Field-Effect Transistors
Gong, Xiaojie,Zheng, Chaoyue,Feng, Xingcui,Huan, Yihong,Li, Jiewei,Yi, Mingdong,Fu, Zhenqian,Huang, Wei,Gao, Deqing
, p. 3920 - 3927 (2018)
There have been many reports on the application of pyrene derivatives as organic semiconductors, but 1,8-subsituted pyrene semiconductors are less well-developed. Two p-type 1,8-substituted pyrene derivatives were synthesized that were composed of a pyrene core, thiophene or bithiophene arms, and end-capped octyl chains. These structures were not completely symmetrical and the dihedral angles between the pyrene core and the adjacent thiophene units had a difference of approximately two degrees. The field-effect performance of these materials was tested on a variety of dielectric surfaces. The performance of both materials with a spin-coated polystyrene layer on SiO2 (PS-treated SiO2) was better than that with an octadecyltrichlorosilane self-assembled monolayer on SiO2 (OTS-treated SiO2), which was mainly attributed to the presence of large grains on the low-leakage and high-capacitance PS films. The thiophene-contained compound presented a hole mobility of up to 0.18 cm2 V?1 s?1 on PS-treated SiO2, which was 45 times that of the bithiophene-contained compound, owing to less steric hindrance, high crystallinity, and large grain size.
Novel phenylcarbazole type organic compounds and an organic electroluminescent device comprising the same
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Paragraph 0157-0160, (2021/06/09)
An organic compound represented by chemical formula 1 and an organic light emitting device including the same are provided. Chemical Formula 1.
Electrochromic properties of pyrene conductive polymers modified by chemical polymerization
Chang, Lijing,Hou, Yanjun,Li, Rui,Ma, Yang,Miao, Shoulei,Wang, Cheng,Xu, Haoran,Zhang, Yuhang
, p. 39291 - 39305 (2021/12/27)
Pyrene is composed of four benzene rings and has a unique planar melting ring structure. Pyrene is the smallest condensed polycyclic aromatic hydrocarbon, and its unique structural properties have been extensively studied. Pyrene has excellent properties such as thermal stability, high fluorescence quantum efficiency and high carrier mobility. This paper mainly used thiophene, EDOT and triphenylamine groups to enhance the pyrene based π-conjugated system and control the molecular accumulation of organic semiconductors, and improve their charge transport performances. Five kinds of polymer were synthesized and correspondingly characterized. The five kinds of pyrene conductive polymer had outstanding properties in terms of solubility, fluorescence intensity and thermal stability, good film-forming properties, stable electrochromic properties and high coloring efficiency. The coloration efficiency (CE) of PPYTP was as high as 277 cm2C?1, and the switching response time was short. The coloring time of PPYEDOT was 1.3 s and the bleaching time was 3.2 s. The lower impedance will also provide the possibility of such polymers being incorporated into electrochromic devices in the future. In short, the synthesized new pyrene conductive polymers will have wide application prospects in the field of electrochromic materials.
Electron-Transfer-Induced Self-Assembly of a Molecular Tweezer Platform
Thakur, Khushabu,Wang, Denan,Mirzaei, Saber,Rathore, Rajendra
supporting information, p. 14085 - 14089 (2020/10/12)
The design and synthesis of a new molecular tweezer (T-tmp) with electron-rich pincers are reported. The stable monocationic radicals and self-assembled dimeric radicals of this molecular tweezer platform were prepared by chemical oxidative titration. With the aid of DFT calculations, it was found that the dimeric radicals with syn-syn-syn conformer has the most stable structure, with the hole primarily delocalized between parallel stacked pyrenyl groups.
O-Doped Nanographenes: A Pyrano/Pyrylium Route Towards Semiconducting Cationic Mixed-Valence Complexes
Dor?evi?, Luka,Allain, Magali,Bonifazi, Davide,Coronado, Eugenio,Demitri, Nicola,Folli, Andrea,Mézière, Cécile,Ma?as-Valero, Samuel,Murphy, Damien,Sallé, Marc,Valentini, Cataldo
supporting information, p. 4106 - 4114 (2020/02/05)
Herein we report an efficient synthesis to prepare O-doped nanographenes derived from the π-extension of pyrene. The derivatives are highly fluorescent and feature low oxidation potentials. Using electrooxidation, crystals of cationic mixed-valence (MV) complexes were grown in which the organic salts organize into face-to-face π-stacks, a favorable solid-state arrangement for organic electronics. Variable-temperature electron paramagnetic resonance (EPR) measurements and relaxation studies suggest a strong electron delocalization along the longitudinal axis of the columnar π-stacking architectures. Electric measurements of single crystals of the MV salts show a semiconducting behavior with a remarkably high conductivity at room temperature. These findings support the notion that π-extension of heteroatom-doped polycyclic aromatic hydrocarbons is an attractive approach to fabricate nanographenes with a broad spectrum of semiconducting properties and high charge mobilities.
