- Synthesis and electro-optical properties of carbazole-substituted pyrene derivatives
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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
- Jeong, Seonju,Park, Sung Hwan,Kim, Ki-Soo,Kwon, Younghwan,Ha, Ki-Ryong,Choi, Byeong-Dae,Han, Yoon Soo
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- A neutral state yellow to navy polymer electrochrome with pyrene scaffold
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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.
- I?i-?zkut, Merve,?zta?, Zahide,Algi, Fatih,Cihaner, Atilla
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- Electrophilic Substitution of Monosubstituted Pyrenes
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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.
- Minabe, Masahiro,Takeshige, Shouji,Soeda, Yuuji,Kimura,Takao,Tsubota, Motohiro
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- Pyrene derivatives with two types of substituents at positions 1, 3, 6, and 8-fad or necessity?
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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.
- Zych, Dawid,Slodek, Aneta
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- A series of short axially symmetrically 1,3,6,8-tetrasubstituted pyrene-based green and blue emitters with 4-tert-butylphenyl and arylamine attachments
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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.
- Zhang, Ran,Zhao, Yun,Zhang, Tengfei,Xu, Lu,Ni, Zhonghai
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- 1,8-Substituted Pyrene Derivatives for High-Performance Organic Field-Effect Transistors
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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.
- Gong, Xiaojie,Zheng, Chaoyue,Feng, Xingcui,Huan, Yihong,Li, Jiewei,Yi, Mingdong,Fu, Zhenqian,Huang, Wei,Gao, Deqing
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- Novel phenylcarbazole type organic compounds and an organic electroluminescent device comprising the same
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An organic compound represented by chemical formula 1 and an organic light emitting device including the same are provided. Chemical Formula 1.
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Paragraph 0157-0160
(2021/06/09)
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- Electrochromic properties of pyrene conductive polymers modified by chemical polymerization
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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.
- Chang, Lijing,Hou, Yanjun,Li, Rui,Ma, Yang,Miao, Shoulei,Wang, Cheng,Xu, Haoran,Zhang, Yuhang
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p. 39291 - 39305
(2021/12/27)
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- O-Doped Nanographenes: A Pyrano/Pyrylium Route Towards Semiconducting Cationic Mixed-Valence Complexes
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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.
- 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
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supporting information
p. 4106 - 4114
(2020/02/05)
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- Electron-Transfer-Induced Self-Assembly of a Molecular Tweezer Platform
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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.
- Thakur, Khushabu,Wang, Denan,Mirzaei, Saber,Rathore, Rajendra
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supporting information
p. 14085 - 14089
(2020/10/12)
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- Templating Porphyrin Anisotropy via Magnetically Aligned Carbon Nanotubes
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The preparation and characterisation of a novel three-dimensional organic material consisting of porphyrin arrays on carbon nanotubes embedded in an organogel is reported. Firstly, the porphyrin array was prepared through metal-ligand coordination of a ditopic ligand (1,2-bis(4-pyridyl)ethane) and two bis-Zn(II) porphyrins, linked through a pyrene core, and was studied through UV-Vis, NMR and diffusion spectroscopies. Secondly, the porphyrin supramolecular architecture was adsorbed on pristine carbon nanotubes, greatly improving the dispersibility of the latter in organic solvents. The hybrid material was characterised by means of UV-Vis spectroscopy, microscopic techniques and thermogravimetric analysis. Finally, by exploiting the anisotropic magnetic susceptibility of carbon nanotubes, the hybrid material was aligned under a magnetic field, the organisation of which could be maintained by in situ gelation. The resultant hybrid organogel exhibited notable optical anisotropy, suggesting an anisotropic arrangement of the porphyrin-CNTs architectures in the macroscopic material.
- ?or?evi?, Luka,Marangoni, Tomas,Liu, Mingjie,De Zorzi, Rita,Geremia, Silvano,Minoia, Andrea,Lazzaroni, Roberto,Ishida, Yasuhiro,Bonifazi, Davide
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p. 1270 - 1278
(2019/02/27)
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- Biphenyl type compound and application thereof to preparation of 1,6-dibromo pyrene
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The invention discloses a biphenyl type compound and application thereof to preparation of 1,6-dibromo pyrene.
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- Highly efficient pyrene blue emitters for OLEDs based on substitution position effect
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To investigate the effect of substitution position of the side group on a pyrene core, three derivatives having a triphenylbenzene group as a bulky side group at the 1,6-position, 4,9-position, and 1,8-position were successfully synthesized: 1,6-bis(5′-phenyl-[1,1':3′,1″-terphenyl]-4-yl)pyrene (1,6-DTBP), 4,9-bis(5′-phenyl-[1,1':3′,1″-terphenyl]-4-yl)pyrene (4,9-DTBP), and 1,8-bis(5′-phenyl-[1,1':3′,1″-terphenyl]-4-yl)pyrene (1,8-DTBP). The three synthesized materials showed excellent thermal stability with a high Tg of >140 °C and a high Td of >500 °C. Due to the highly twisted structure of 1,8-DTBP in the film state, the absolute photoluminescence quantum yield value was improved. Of the three synthesized materials used as an emitter in a non-doped organic light-emitting diode device, 1,8-DTBP showed highly efficient electroluminescence performance, with a luminance efficiency of 6.89 cd/A, power efficiency of 3.03 lm/W, and external quantum efficiency of 7.10% at 10 mA/cm2. In addition, 4,9-DTBP showed a deep-blue emission of CIE x, y (0.158, 0.063) suitable for HD-TV.
- Jung, Mina,Lee, Jaehyun,Jung, Hyocheol,Kang, Seokwoo,Wakamiya, Atsushi,Park, Jongwook
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- Preparation of a hyperbranched porous polymer and its sensing performance for nitroaromatics
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A hyperbranched porous polymer P based on adamantane and pyrene was synthesized through the Sonogashira coupling reaction. The three-dimensional rigid molecular skeleton of adamantane makes polymer P porous. Compound M, which acts as the block moiety between two adamantane groups in polymer P, was also synthesized for the control experiment. Compared with M, the characteristics of P changed remarkably with it exhibiting different emission behaviors and performances for the detection of DNT. In saturated DNT vapor, the quenching efficiency (ηEP) of film P (82%) was remarkably superior compared with that of film M (22%). In addition, a series of films with different thicknesses and different amounts of polymer P were prepared. Results showed that the quenching efficiencies did not change with an increase in the film thickness.
- Wu, Hongtao,Xu, He,Tao, Furong,Su, Xi,Yu, William W.,Li, Tianduo,Cui, Yuezhi
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p. 12802 - 12810
(2018/08/04)
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- Organic compound, and application thereof in electroluminescent device
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The invention provides an organic compound, which is shown in the formula I. The invention further provides application of the organic compound in an electroluminescent device. The organic compound can effectively improve the performance of the electroluminescent device.
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Paragraph 0056; 0057; 0058; 0059
(2017/06/02)
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- Chemical synthesis and application research of cyanogroup containing functional material for modifying perovskite layer in perovskite solar cell
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The invention aims at designing and synthesizing a cyanogroup compound and modifying a perovskite layer in a perovskite solar cell structure. According to an implementation method, a layer of modification material is arranged on the surface of perovskite in a spin coating manner, cyanogroups in material molecules and I in the perovskite structure interact, surface charges of the modification material are dispersed, meanwhile, I migration is reduced, and therefore the stability of the perovskite layer is improved; and benzene ring and alkyl chain components in the molecular structure can achieve the functions of improving interfacial compatibility and reducing the surface defects, and finally the aim of improving the performance of a perovskite solar cell is achieved. Ar in a chemical formula (1) (please see the specification) is a following aromatic compound (please see the specification). Ar in a chemical formula (2) (please see the specification) is a following aromatic compound (please see the specification). R1 is -CN or a chemical formula (please see the specification), and R2 is 1-16 alkyl chains.
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Paragraph 0022; 0029; 0030
(2017/05/23)
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- A new series of short axially symmetrically and asymmetrically 1,3,6,8-tetrasubstituted pyrenes with two types of substituents: Syntheses, structures, photophysical properties and electroluminescence
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A new series of short axially symmetrically (4a and 4b) and asymmetrically (4c and 4d) 1,3,6,8-tetrasubstituted pyrene-based compounds with two phenyl moieties and two diphenylamine units on the 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 structures of 4a and 4b were determined by single-crystal X-ray diffraction analysis, indicating that the compounds are twisted by the peripheral substituents and the intermolecular π-π interactions have been efficiently interrupted. The four compounds exhibit high absolute fluorescence quantum yields (ФF) in dichloromethane (83.31–88.45%) and moderate ФFs in film states (20.78–38.68%). In addition, compounds 4a and 4b display relatively higher absolute ФFs than those of 4c and 4d in film states. All the compounds exhibit high thermal stability with decomposition temperatures above 358?°C and the values of 4c and 4d are higher than 4a and 4b. Compounds 4a and 4b can form morphologically stable amorphous thin films with Tg values of 146?°C and 149?°C, respectively. However, there are no obvious Tg observed in compounds 4c and 4d. Electroluminescent devices using 4a and 4b as doped emission layer show promising device performance with low turn-on voltage (3.0?V), maximum brightness around 15100?cd/m2 and 16100?cd/m2, maximum luminance efficiency of 12.4?cd/A and 13.6?cd/A and maximum external quantum efficiency of 5.34% and 5.63%, respectively.
- Zhang, Ran,Zhang, Tengfei,Xu, Lu,Han, Fangfang,Zhao, Yun,Ni, Zhonghai
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p. 237 - 246
(2016/08/04)
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- Pyrene compound comprising the compound and organic light emitting diode device
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A pyrene compound and an organic light emitting diode device including the same are disclosed. The organic light emitting diode device includes at least two stacks provided between a first electrode and a second electrode, and a charge generation layer provided between the stacks and including an N type charge generation layer and a P type charge generation layer, wherein the N type charge generation layer is made of the pyrene compound.
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Paragraph 0068-0072
(2016/10/08)
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- COMPOUNDS FOR ORGANIC OPTOELECTRONIC DEVICE AND ORGANIC OPTOELECTRONIC DEVICE INCLUDING THE SAME
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Provided are a compound for an organic optoelectronic device represented by chemical formula 1, and an organic optoelectronic device comprising the same. In chemical formula 1, each of Ar^1 and Ar^2 is independently a substituted or unsubstituted C6 to C20 aryl group, or Ar^1 and Ar^2 are linked to form an N-containing heterocycle. Each of Ar^3 and Ar^4 is independently a substituted or unsubstituted C6 to C20 aryl group, and R is a C6 to C30 arylene group or a C6 to C30 arylene group substituted by a C1 to C10 alkyl group.COPYRIGHT KIPO 2016
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Paragraph 0112-0116
(2017/01/05)
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- Contorted aromatics: Via a palladium-catalyzed cyclopentannulation strategy
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We show that a new class of contorted polycyclic aromatic hydrocarbons (PAHs) containing five-membered rings can be prepared via a palladium-catalyzed cyclopentannulation followed by Scholl cyclodehydrogenation. The annulation chemistry can be accomplished between a di-arylethynylene and an appropriate aryl-dibromide to form 1,2,6,7-tetraarylcyclopenta[hi]aceanthrylenes and 1,2,6,7-tetraaryldicyclopenta[cd,jk]pyrenes. Scholl cyclodehydrogenation to close the externally fused aryl groups was accomplished only with properly arranged alkoxy substitutions and provides access to the pi-extended 2,7,13,18-tetraalkoxytetrabenzo[f,h,r,t]rubicenes and 2,7,13,18-tetraalkoxydibenzo[4,5:6,7]indeno[1,2,3-cd]dibenzo[4,5:6,7]indeno[1,2,3-jk]pyrenes. The final compounds each possess apparent [4]helicene-like arrangements with fused five-membered rings; however, only the 2,7,13,18-tetraalkoxytetrabenzo[f,h,r,t]rubicenes contort out of planarity owing to an additional [5]helicene like arrangement. Single crystal analysis of the contorted aromatic shows the PAHs stack in a lock-and-key like arrangement and pi-stack in a columnar arrangement. Solution-phase aggregation, as well as liquid crystalline mesophases, were found for derivatives with suitably attached solubilizing chains.
- Bheemireddy, Sambasiva R.,Ubaldo, Pamela C.,Finke, Aaron D.,Wang, Lichang,Plunkett, Kyle N.
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supporting information
p. 3963 - 3969
(2016/06/15)
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- Synthesis and physical properties of new pyrene derivative with bulky side groups for blue emission
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Organic light-emitting diodes (OLEDs) have attracted much attention from academia and industry field because of their various applications such as large area flat-panel displays and lightings. We designed and synthesized new pyrene derivative with 1,6-bis(3',5'-diphenylbiphenyl-4-yl)pyrene (1,6-DTBP) which has bulky side group for intra-twisted structure and blue emission. In solution state, 1,6-DTBP exhibited absorption maximum value of 365 nm and photoluminescence (PL) maximum value of 425 nm. In film state, 1,6-DTBP exhibited absorption maximum value of 373 nm and PL maximum value of 461 nm without excimer band. 1,6-DTBP can be applicable to OLED emitter as a blue emission.
- Jung, Mina,Lee, Jaehyun,Jung, Hyocheol,Park, Jongwook
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p. 8796 - 8799
(2016/07/27)
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- Novel 1,8-bis(diarylamino)pyrenes as OLED materials
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New soluble electroluminescent pyrene derivatives, namely, 1,8-bis(diarylamino)pyrenes, have been synthesized by the Buchwald–Hartwing cross-coupling. Light-emitting devices based on these derivatives have been prepared.
- Kaplunov, Mikhail G.,Yakushchenko, Igor K.,Krasnikova, Svetlana S.,Echmaev, Sergei B.
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p. 437 - 439
(2016/10/05)
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- Two Symmetrically Bis-substituted Pyrene Derivatives: Synthesis, Photoluminescence, and Electroluminescence
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Two kinds of cyanophenyl terminated pyrene derivatives for organic light-emitting diodes were synthesized and characterized by UV/Vis, fluorescence (FL), 1H NMR, MALDI-TOF, CV and TGA. Both compounds exhibited blue photoluminescence and high fluorescent quantum yield of 85% and 75% in solutions. Due to the presence of acetylene spacer, the compound distinguishes itself by high coplanarity, high thermal stability, little Stokes' shift and clear excimer formation in the solid state from the acetylene-free compound. In order to suppress the molecular aggregation, the electroluminescent properties were studied by doing the materials in PVK. The result proved that energy transfer happened from the host PVK to the materials. Two kinds of cyanophenyl terminated pyrene derivatives for OLEDs were synthesized and characterized. Both compounds exhibited blue photoluminescence and high fluorescent quantum yield of 85% and 75% in solutions. The result proved that energy transfer happened from the host PVK to the materials.
- Gong, Xiaojie,Xie, Xiang,Chen, Naiwu,Zheng, Chaoyue,Zhu, Jie,Chen, Runfeng,Huang, Wei,Gao, Deqing
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p. 967 - 973
(2015/09/01)
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- The optical properties and quantum chemical calculations of thienyl and furyl derivatives of pyrene
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A detailed electrochemical, photophysical and theoretical study is presented for various new thienyl and furyl derivatives of pyrene. Their optical properties are described based on UV-VIS absorption and both steady-state and time-resolved fluorescence spectroscopy. DFT and TDDFT calculations are also presented to support experimental data. The calculations results show that HOMO-LUMO orbitals are delocalized uniformly between aromatic core and aryl substituents. Good electrochemical stability of thienyl and furyl hybrids of pyrene confirm their potential application for light emitting electrochemical cells or spintronics mainly due to their beneficial optical and charge transport properties in electrochromic devices. In order to demonstrate this potential, an OLED device is presented. Synthesized compounds included in this OLED device both facilitate electron transport and act as a light emitting layer.
- Idzik, Krzysztof R.,Cywiński, Piotr J.,Kuznik, Wojciech,Frydel, Jaroslaw,Licha, Tobias,Ratajczyk, Tomasz
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p. 22758 - 22769
(2015/09/07)
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- POLYMERS CONTAINING 2,7-PYRENE STRUCTURAL UNITS
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The present invention relates to polymers containing 2,7-pyrene structural units, to a process for the preparation thereof, and to blends and formulations comprising these polymers. The present invention furthermore relates to the use of the polymers or blends according to the invention in electronic devices and to electronic devices, in particular OLEDs, comprising the polymers or blends according to the invention.
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- Synthesis and electroluminescence properties of highly efficient dual core chromophores with side groups for blue emission
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Highly efficient blue emitting materials consisting of dual core derivatives with phenyl and/or naphthyl side groups and asymmetric or symmetric structures were designed and synthesized. The asymmetric structures 1-naphthalen-1-yl-6-(10-phenyl-anthracen-9-yl)-pyrene (Ph-AP-Na) and 1-(10-naphthalen-1-yl-anthracen-9-yl)-6-phenyl-pyrene (Na-AP-Ph), and the symmetric structures 1-phenyl-6-(10-phenyl-anthracen-9-yl)-pyrene (Ph-AP-Ph) and 1-naphthalen-1-yl-6-(10-naphthalen-1-yl-anthracen-9-yl)-pyrene (Na-AP-Na) were synthesized. Of the synthesized compounds, Na-AP-Na was found to exhibit the highest EL device efficiency of 5.46 cd A-1. Ph-AP-Na, Na-AP-Ph, Ph-AP-Ph, and Na-AP-Na exhibit EL maximum values of real blue color in the range 455 nm to 463 nm. The y values of their color coordinates are within the range 0.125 to 0.142, so these compounds exhibit good blue color coordinates for displays. The lifetime of the Na-AP-Na device was more than three times longer than that of the AP dual core (1-anthracen-9-yl-pyrene) device. This journal is the Partner Organisations 2014.
- Lee, Hayoon,Kim, Beomjin,Kim, Seungho,Kim, Joonghan,Lee, Jaehyun,Shin, Hwangyu,Lee, Ji-Hoon,Park, Jongwook
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p. 4737 - 4747
(2014/06/23)
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- Furyl derivatives of pyrene: Efficient synthesis and relevant optical properties
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A series of various furyl derivatives of pyrene were synthesized by Stille cross-coupling procedure. Their structures were characterized by nuclear magnetic resonance, and elemental analysis. Optical properties of the synthesized materials as well as their energy levels were investigated by ultraviolet-visible absorption supported by fluorescence spectra. All of the studied compounds exhibit fluorescence with energy peaks dependent on the number of furyl substituents. Furthermore, quantum mechanical modeling method of obtained materials are studied. Experimental data are focused on quantum chemical calculations. Highest occupied molecular and lowest unoccupied molecular orbitals are delocalized uniformly on both pyrene core and furyl substituents. Furanyl-pyrene hybrids are potentially good materials for optical applications mainly due to their optical and charge transport properties, which are also desired for electronic applications.
- Idzik, Krzysztof R.,Ledwon, Przemyslaw,Licha, Tobias,Kuznik, Wojciech,Lapkowski, Mieczyslaw,Frydel, Jaroslaw
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- Synthesis and optical properties of various thienyl derivatives of pyrene
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A series of various thienyl derivatives of pyrene were synthesized by Stille cross-coupling procedure. Their structures were characterized by 1H NMR, 13C NMR and elemental analysis. The spectroscopic characteristics were investigated by UV-vis absorption and fluorescence spectra. Based on quantum chemical calculations, the energy levels of investigated molecules with respect to the pyrene molecule were also discussed.
- Idzik, Krzysztof R.,Licha, Tobias,Lukes, Vladimir,Rapta, Peter,Frydel, Jaroslaw,Schaffer, Mario,Taeuscher, Eric,Beckert, Rainer,Dunsch, Lothar
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p. 153 - 160
(2014/03/21)
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- A novel pyrene-containing fluorescent organogel derived from a quinoline-based fluorescent porbe: Synthesis, sensing properties, and its aggregation behavior
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A new family of pyrene-containing compounds 2-4 derived from aminoquinoline-containing fluorescent probe 1 were successfully synthesized and well characterized. The investigation of the absorption and emission spectra of these compounds revealed that the photophysical properties were significantly affected by the substitution of pyrene. Moreover, these compounds exhibited selective fluorescence behaviour towards Zn2+ in aqueous solution. The gelation properties of these compounds were investigated by the "stable to inversion of a test tube" method. Interestingly, 1,8-bis-substituted compound 4 displayed stable gel-formation properties in acetone, dioxane, tetrahydrofuran, ethyl acetate, chloroform, and dichloromethane. The morphologies of the xerogels were investigated by scanning electron microscopy (SEM) and laser scanning confocal microscopy (LSCM). The concentration- and temperature-dependent emission properties, and concentration- and temperature-variable 1H NMR spectroscopy of compound 4 were investigated, which suggested that both π-π stacking interaction and hydrogen bonding were the driving forces for the process of self-aggregation and the gel formation. In addition, studies on the luminescence properties indicated that 4 had the ability to form a fluorescent organogel with interesting fluorescence behaviour. More importantly, it was found that compound 4 could form a stimuli-responsive gel that had a sensitive gel-to-sol transition response to heating or adding Zn2+. the Partner Organisations 2014.
- Huang, Chang-Bo,Chen, Li-Jun,Huang, Junhai,Xu, Lin
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p. 19538 - 19549
(2014/05/20)
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- Effect of alkoxy terminal chain length on mesomorphism of 1,6-disubstituted pyrene-based hexacatenar liquid crystals: Columnar phase control
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Synthesis and mesophase-transition behaviors of six 1,6-disubstituted pyrene-based hexacatenar liquid crystals 1n (n=8-18) are reported here. They were synthesized by the Sonogashira coupling between 1,6-diethynylpyrene and 2-bromothiophene bearing a trialkoxybenzoyl group. The phase-transition behavior was studied by differential scanning calorimetry and polarized optical microscopy; a few mesophase progressions, I-Col/I-X-Col and Col-Sm, were observed, where X was an optically isotropic but unidentified phase. The structures of Colr, Colh, and Sm phases were analyzed by the X-ray crystallography, and the effect of the terminal alkoxy chain length on the mesomorphism was evaluated.
- Hirose, Takuji,Takai, Hiroaki,Watabe, Mizuki,Minamikawa, Hiroyuki,Tachikawa, Tatsuya,Kodama, Koichi,Yasutake, Mikio
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p. 5100 - 5108
(2014/07/08)
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- Effect of alkoxy terminal chain length on mesomorphism of 1,6-disubstituted pyrene-based hexacatenar liquid crystals: Columnar phase control
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Synthesis and mesophase-transition behaviors of six 1,6-disubstituted pyrene-based hexacatenar liquid crystals 1n(n=8-18) are reported here. They were synthesized by the Sonogashira coupling between 1,6-diethynylpyrene and 2-bromothiophene bearing a trialkoxybenzoyl group. The phase-transition behavior was studied by differential scanning calorimetry and polarized optical microscopy; a few mesophase progressions, I-Col/I-X-Col and Col-Sm, were observed, where X was an optically isotropic but unidentified phase. The structures of Colr, Colh, and Sm phases were analyzed by the X-ray crystallography, and the effect of the terminal alkoxy chain length on the mesomorphism was evaluated.
- Hirose, Takuji,Takai, Hiroaki,Watabe, Mizuki,Minamikawa, Hiroyuki,Tachikawa, Tatsuya,Kodama, Koichi,Yasutake, Mikio
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p. 5100 - 5108
(2014/12/10)
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- Synthesis, structural and spectral properties of diarylamino-functionalized pyrene derivatives via Buchwald-Hartwig amination reaction
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A new series of diarylamino-functionalized pyrene derivatives, namely, 1-(N,N-diarylamino)-substituted pyrenes (7), isomer of 1,6-bis- and 1,8-bis(N,N-diarylamino)-substituted pyrenes (8/9) and 1,3,6,8-tetrakis(N,N- diarylamino)-substituted pyrenes (10) have been synthesized. The structures of these synthesized compounds were determined on the basis of spectral data and elemental analysis. All compounds 7-10 have bright fluorescent emissions from sky-blue to green in solution condition (λmax = 464-500 nm in CH2Cl2) and high emission efficiency (Φf = 0.84-0.96 in dichloromethane). All compounds have high thermal stability and good solubility in common organic solvents. The electronic properties of these compounds were determined by spectroscopic methods such as UV-vis absorption spectroscopy and fluorescence emission spectroscopy. Clear evidences were obtained that the longest wavelength bands of these compounds are bathochromically red-shifted as the number of the diarylamino-substituent increased.
- Hu, Jian-Yong,Feng, Xing,Seto, Nobuyuki,Do, Jung-Hee,Zeng, Xi,Tao, Zhu,Yamato, Takehiko
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- COMPOUNDS FOR ELECTRONIC DEVICES
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The present invention relates to organic electroluminescent devices comprising compounds of the formula (1), in particular as blue singlet emitting materials in an electroluminescent layer.
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Page/Page column 24
(2014/01/08)
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- Photovoltaic devices using semiconducting polymers containing head-to-tail-structured bithiophene, pyrene, and benzothiadiazole derivatives
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An alternating copolymer composed of heal-to-tail-structured 3,4'-dihexyl-2,2'-bithiophene (DHBT) and pyrene units [poly(DHBT-alt-PYR)] was synthesized using a Stille coupling reaction for use in photovoltaic devices as a p-type donor. For the reduction of the bandgap energy of poly(DHBT-alt-PYR), 4,7-bis(3'-hexyl-2,2'-bithiophen-5-yl)benzo[c][1,2,5]thiadiazole (BHBTBT) units were introduced into the polymer. Poly(DHBT-co-PYR-co-BHBTBT)s were synthesized using the same polymerization reaction. The synthesized polymers were soluble in common organic solvents and formed smooth thin films after spin casting. The optical bandgap energies of the polymers were obtained from the onset absorption wavelengths. The measured optical bandgap energy of poly(DHBT-alt-PYR) was 2.47 eV. As the BHBTBT content in the ter-polymers increased, the optical bandgap energies of the resulting polymers decreased. The bandgap energies of poly(50DHBT-co-40PYR-co-10BHBTBT) and poly(50DHBT-co-20PYR-co-30BHBTBT) were 1.84 and 1.73 eV, respectively. Photovoltaic devices were fabricated with a typical sandwich structure of ITO/PEDOT:PSS/active layer/LiF/Al using the polymers as electron donors and [6,6]-phenyl C71-butyric acid methyl ester as the electron acceptor. The device using poly(50DHBT-co-20PYR-co- 30BHBTBT) showed the best performance among the fabricated devices, with an open-circuit voltage, short-circuit current, fill factor, and maximum power conversion efficiency of 0.68 V, 5.54 mA/cm2, 0.35, and 1.31%, respectively.
- Kim, Ji-Hoon,Lee, Sunyoung,Kang, In-Nam,Park, Moo-Jin,Hwang, Do-Hoon
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experimental part
p. 3415 - 3424
(2012/08/29)
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- Incorporation of pyrene units to improve hole mobility in conjugated polymers for organic solar cells
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Solution-processable semiconducting copolymers, poly[N-9′- heptadecanyl-2,7-carbazole-alt-5,5′-(4′,7′-di-2-thienyl- 2′,1′,3′-benzothiadiazole)] (PCDTBT) and poly[4,8-bis(2- ethylhexyl-2-thenyl)-benzo[1,2-b:4,5-b′]dithiophene-alt-5, 5′-(4′,7′-di-2-thienyl-2′,1′,3′- benzothiadiazole)] (PBDTDTBT), and their pyrene-containing terpolymers were synthesized using Suzuki or Stille coupling. Pyrene units were introduced to improve the charge-transporting abilities of the polymers. The resulting polymers were found to be soluble in common organic solvents and formed smooth and uniform spin-coated thin films. They also exhibited good thermal stability and lost 71BM/Ca/Al configuration fabricated using the pyrene-containing polymers had higher power conversion efficiencies than those using the corresponding parent polymers.
- Kim, Ji-Hoon,Kim, Hee Un,Kang, In-Nam,Lee, Sang Kyu,Moon, Sang-Jin,Shin, Won Suk,Hwang, Do-Hoon
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p. 8628 - 8638
(2013/01/15)
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- Design and preparation of platinum-acetylide organogelators containing ethynyl-pyrene moieties as the main skeleton
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A series of new platinum-acetylide complexes containing ethynyl-pyrene moieties as the main skeleton were synthesized and characterized. The investigation of the absorption and emission spectra of these complexes revealed that the extension of the molecular size with the introduction of different numbered platinum-acetylide fragments can efficiently tune the absorption and emission bands from the UV to the longer wavelength region. Moreover, the gelation properties of these complexes were investigated by the "stable-to-inversion-of-a-test-tube" method. Most newly designed platinum-acetylide compounds presented a stable gel-formation property in some of the tested solvents. The morphology of the xerogels was investigated by scanning electron microscopy (SEM). Furthermore, the concentration- and temperature-dependent absorption and emission properties of these complexes were investigated, which support the formation of J-type assemblies during the aggregation process. More importantly, it was found that the complexes 4 a-C6, 4 a, and 4 a-C18 with four platinum-acetylide fragments presented potential applications as luminescent organometallic gels.
- Xu, Xing-Dong,Zhang, Jing,Yu, Xudong,Chen, Li-Jun,Wang, De-Xian,Yi, Tao,Li, Fuyou,Yang, Hai-Bo
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p. 16000 - 16013
(2013/02/23)
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- Synthesis of unsymmetrically substituted pyrene derivatives through (6-bromo-3,8-dibutylpyren-1-yl)trimethylsilane
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A straightforward route to unsymmetrically functionalized pyrene derivatives is described involving the synthesis of key precursor (6-bromo-3,8-dibutylpyren-1-yl)trimethylsilane 1. In a first step bromide 1 was successful in Suzuki-Miyaura, Sonogashira, and Buchwald-Hartwig cross-coupling reactions. Subsequent transformation of the trimethylsilyl group to bromide enabled the introduction of a second variable functional group onto the pyrene skeleton.
- Sato, Akihiro H.,Maeda, Mine,Mihara, Shigenori,Iwasawa, Tetsuo
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supporting information; scheme or table
p. 6284 - 6287
(2011/12/14)
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- Mild persubstitution of di- and tetrabrominated arenes with arylthiolate nucleophiles
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A mild selective protocol was used to prepare tetrakis(2-chlorophenylthio) anthracene from tetrabromoanthracene and sodium 2-chlorobenzenethiolate avoiding the thiolate self-attack. The uncatalyzed nucleophilic substitution of a series of mono-, di-, and tetrabrominated arenes by arylthiolate ions was attempted in mild conditions to investigate the scope of the substitution reaction regarding the size of the aromatic system as well as the number of bromine atoms. Successful reactions afforded only the persubstituted products in good purity and yield after a simple workup and chemoselectivity of Br versus Cl substituents was achieved for the tetrabromide.
- Del Rosso, Pablo G.,Almassio, Marcela F.,Bruno, Mattia,Garay, Raúl O.
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supporting information; body text
p. 6730 - 6733
(2011/02/25)
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- Synthesis and fluorescence emission properties of 1,3,6,8-tetrakis(9H- fluoren-2-yl)pyrene derivative
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A novel pyrene-based highly pure blue fluorescent and stable molecule, 1,3,6,8-tetrakis[9,9-bis(3-methylbutyl)-9Hfluoren- 2-yl]pyrene, was successfully synthesised via a Pd-catalysed Suzuki coupling reaction of 1,3,6,8- tetrabromopyrene with 2-[9,9-bis(3-methylbutyl)-9H-fluoren-2-yl]-4,4,5,5- tetramethyl[1,3,2]dioxaborolane. The photoproperties of this pyrene were examined in detail and these data indicated its potential application as blue-emitting materials in organic light-emitting diodes.
- Hu, Jian-Yong,Hiyoshi, Hidetaka,Do, Jung-Hee,Yamato, Takehiko
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experimental part
p. 278 - 282
(2010/10/19)
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- Photoinitiated charge transport through π-stacked electron conduits in supramolecular ordered assemblies of donor-acceptor triads
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Photochemical electron donor-acceptor triads having an aminopyrene primary donor (APy) and a p-diaminobenzene secondary donor (DAB) attached to either one or both imide nitrogen atoms of a perylene-3,4:9,10-bis(dicarboximide) (PDI) electron acceptor were
- Bullock, Joseph E.,Carmieli, Raanan,Mickley, Sarah M.,Vura-Weis, Josh,Wasielewski, Michael R.
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supporting information; scheme or table
p. 11919 - 11929
(2009/12/08)
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- Reversible photoinduced change in molecular ordering of diarylethene derivatives at a solution-HOPG interface
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A diarylethene-pyrene diad and a diarylethene-pyrene-diarylethene triad were synthesized to investigate the photoinduced two-dimensional ordering change at a solution-HOPG interface. The molecular arrangements were detected by STM. The different photochromic isomers showed different orderings reflecting the differences in their molecular structures. For the diarylethene-pyrene- diarylethene triad, a new ordering appeared upon irradiation with UV light and returned to the original ordering upon subsequent irradiation with visible light. The new arrangement was assigned to the ordering of the closed-closed isomers based on the images of the isolated open- and closed-isomers. The relationship between the nature of the two-dimensional ordering and the molecular structure is discussed.
- Arai, Ryota,Uemura, Shinobu,Irie, Masahiro,Matsuda, Kenji
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supporting information; experimental part
p. 9371 - 9379
(2009/02/02)
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- Dialkynylpyrenes: Strongly fluorescent, environment-sensitive DNA building blocks
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Two isomeric dialkynylpyrene phosphoramidites and their incorporation into oligonucleotides are described. The pyrene units closely resemble the well-known perylene bisimide dye PDI with regard to the ability to self-organize within a DNA duplex. In addition, dialkynylpyrenes exhibit significant monomer and remarkably strong excimer fluorescence. The dialkynylpyrene building blocks are promising candidates for applications in diagnostic tools, such as excimer-based molecular beacons, as well as for novel DNA-based materials with special optical properties. Copyright
- Bittermann, Holger,Siegemund, Doreen,Malinovskii, Vladimir L.,Haener, Robert
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supporting information; experimental part
p. 15285 - 15287
(2009/03/11)
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- Reaction of polycyclic aromatic hydrocarbons adsorbed on silica in aqueous chlorine
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The reaction of polycyclic aromatic hydrocarbons (PAHs) previously adsorbed on silica gel or diatomaceous earth with sodium hypochlorite was carried out to elucidate their reactivity to aqueous chlorine. It was demonstrated that the PAHs adsorbed on silica reacted more rapidly than the PAHs themselves in water, leading to the formation of many chlorinated and oxidized derivatives. A similar reaction in the presence of potassium bromide was found to preferentially produce corresponding brominated derivatives. These reactions seem to proceed through PAHs adsorbed on the silica surface and halogenating agents, the electrophilicity of which may be raised by the catalytic effect of the silanol group of the silica surface. These findings from the environmental viewpoint suggest that the reaction of hydrophobic compounds adsorbed on sediment cannot be neglected.
- Nakamura, Hideyuki,Tomonaga, Yuzo,Miyata, Kana,Uchida, Mitsuo,Terao, Yoshiyasu
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p. 2190 - 2195
(2007/10/03)
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- COMPOUND HAVING SPIRO BOND, MATERIAL FOR LUMINESCENT COATING FORMATION AND ORGANIC ELECTROLUMINESCENCE ELEMENT INCLUDING THE SAME
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A novel compound having a spiro bond with a specific structure, a material for forming a luminous coated film comprising the compound having the spiro bond with the specific structure, and an organic electroluminescence device which comprises at least one organic thin film layer sandwiched between a pair of electrode consisting of an anode and a cathode, wherein the organic thin film layer comprises the compound having the spiro bond. The organic EL device employing either the compound having a spiro bond or the material for forming luminous coated film in accordance with the present invention is superior in heat resistance, has stability of the thin film composing the device, emits uniform blue light, and exhibits an excellent luminance, current efficiency even under a low driving voltage.
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Page/Page column 37
(2010/11/08)
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- Pyrene-fused porphyrins: Annulation reactions of meso-pyrenylporphyrins
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We prepared novel pyrene-fused porphyrins via the oxidative intramolecular ring closure reactions of meso-pyrenylporphyrin. The excitation energies and the oxidation potentials of the isolated dark-colored pyrene-fused porphyrins were significantly low compared with those of the corresponding precursors.
- Yamane, Osamu,Sugiura, Ken-Ichi,Miyasaka, Hitoshi,Nakamura, Kazuya,Fujimoto, Tatsuhiko,Nakamura, Kazuki,Kaneda, Takahiro,Sakata, Yoshiteru,Yamashita, Masahiro
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- Pyrenylboronic acids as a novel entry for photochemical DNA cleavage: diradical-forming pyrene-1,6-diyldiboronic acid mimics the cleavage mechanism of enediyne antitumor antibiotics
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Pyren-1-ylboronic acid 4 and pyrene-1,6-diyldiboronic acid 5 are bound to supercoiled double-strand circular DNA plasmid ColE1 (colDNA) and effect its efficient photocleavage under visible light irradiation.Mechanistic studies show that the cleavage occurs according to the radical mechanism.The cleavage activity of monoacid 4 could be suppressed by the addition of D-fructose because of boronic acid-saccharide complexation.Diacid 5 is bound to colDNA more strongly than is monoacid 4 and effects its efficient photocleavage to yield Form III.The results show that diradical-forming diacid 5 is able to cleave DNA at two reaction sites, mimicking the cleavage mechanism of enediyne antitumor antibiotics.
- Suenaga, Hikaru,Nakashima, Kazuaki,Mizuno, Toshihisa,Takeuschi, Masayuki,Hamachi, Itaru,Shinkai, Seiji
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p. 1263 - 1268
(2007/10/03)
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