36809-26-4Relevant articles and documents
Comparison of two strategies to improve organic ternary memory performance: 3-Hexylthiophene linkage and fluorine substitution
Bao, Qing,Li, Hua,Li, Yang,He, Jinghui,Xu, Qingfeng,Li, Najun,Chen, Dongyun,Wang, Lihua,Lu, Jianmei
, p. 306 - 313 (2016)
In this paper, two acceptor-donor-acceptor (A-D-A) type organic small molecules, 4,4'-(5,5'-(benzo[c] [1,2,5]thiadiazole-4,7-diyl)bis(3-hexylthiophene-5,2-diyl))bis(N-(4-nitrophenyl)-N-phenylaniline) (NTPA2TBT) and 4,4'-(5,6-difluorobenzo[c] [1,2,5]thiadiazole-4,7-diyl)bis(N-(4-nitrophenyl)-N-phenylaniline) (NTPA2BTF2), were synthesized and fabricated into resistive random access memory devices. Compared with our previously reported molecule NTPA2BT, NTPA2TBT has 3-hexylthiophene linkages bridging its donor and acceptor, while there are two additional fluorine atoms in the benzothiadiazole moiety for NTPA2BTF2. Both the fabricated memory devices based on these two new molecules perform nonvolatile ternary memory characteristics with lower threshold voltages, higher reproducibility and better stability. The addition of 3-hexylthiophene bridges significantly promotes the planarity of the conjugation backbone and facilitates the molecular stacking, while the substitution hydrogen by fluorine improves the intermolecular interaction, and thus also induces an ordered molecular stacking. The insertion of 3-hexylthiophene bridges or fluorine atoms could be an effective strategy of tailoring organic molecules to improve data storage performance with lower power consumption.
Unexpected De-arylation of a pentaaryl fullerene
Clavaguera, Simon,Khan, Saeed I.,Rubin, Yves
, p. 1389 - 1391 (2009)
A triphenylamine-derived pentaaryl fullerene undergoes an unusual oxidative dearylation under basic conditions to give tetraarylated epoxy fullerene in high yield. The structure of the product was confirmed by single crystal X-ray diffraction. A mechanism is proposed to account for the loss of the addend and the subsequent formation of the epoxide group.
13C NMR Study of ortho-, meta- and para-Substituted Phenylhiphenylamines: Substituent Effect Correlations
Grimley, Eugene,Collum, David H.,Alley, Earl G.,Layton, Bobby
, p. 296 - 302 (1981)
The 13C chemical shifts of 11 substituted triphenylamines have been determined and the assignment of these resonances made using intensities, 1H and 19F couplings and predictions from bond additivity relationships. 13C chemical shifts at carbons bearing the substituent and at carbons ortho to the substituent correlated reasonably well with the Q parameter.A multiple regression analysis of chemical shifts with the field and resonance parameters of Swain and Lupton and the Q parameter produced significantly better correlations than those obtained when Q was omitted for these positions. 13C chemical shift correlations for carbons meta and para to the substituent were not significantly better than when Q was omitted.Significant correlations were obtained between field and resonance parameters and 13C chemical shifts of C-o and C-p, and C-i, C-o, C-m and C-p of the non-substituent bearing phenyl rings in ortho- and para-substituted phenyldiphenylamines, respectively.
The improvement of photovoltaic performance of quinoline-based dye-sensitized solar cells by modification of the auxiliary acceptors
?i?man, ?lkay,Arkan, Burcu,Arslan, Bar?? Se?kin,Avc?, Davut,Derin, Yavuz,Gezgin, Merve,Nebio?lu, Mehmet,Tutar, Ahmet
, (2020/10/07)
Three new dyes containing diphenylamine as electron donor, benzene (BIM1), benzothiadiazole (BTD) (BIM2) and N-ethylhexylbenzotriazole (BTZ) (BIM3) as auxiliary electron acceptors, quinoline as π-bridge and cyanoacrylic acid as anchoring group were synthesized in D-A-π-A structure for use in dye-sensitized solar cells (DSSCs). The optical, electrochemical, theoretical and photovoltaic methods were performed to understand the auxiliary acceptor influence on the performance of these dyes. Compared to the other dyes, the DSSC with dye BIM3 slightly increases the open circuit voltage (Voc) owing to the retardation of charge recombination by BTZ. However, replacement of benzene or BTZ by BTD unit causes a large red shift of the absorption spectra, leading BIM2 cell to produce the highest short circuit current density (Jsc). Thus, among the three D-A-π-A dyes, BIM2 is determined to be the most efficient dye, which reached a Voc of 0.627 V and Jsc of 11.53 mA cm–2, corresponding to an overall power conversion efficiency of 5.21 % in the presence of chenodeoxycholic acid (CDCA) as the coadsorbent. These results suggest that the insertion of benzothiadiazole as auxiliary acceptor into quinoline-based D-A-π-A dyes can effectively improve photovoltaic performance of DSSCs.
Multi-fold Sonogashira coupling: A new and convenient approach to obtain tetraalkynyl anthracenes with tunable photophysical properties
Islam, Khadimul,Narjinari, Himani,Bisarya, Akshara,Kumar, Akshai
, p. 9692 - 9704 (2021/11/30)
For the first time, a direct single-step one-pot route to access nine new symmetric tetraalkynylated anthracenes via Pd(CH3CN)2Cl2/cataCXiumA catalyzed tetra-fold Sonogashira coupling is reported. Five of these tetraalkynylated anthracenes have been crystallographically characterized, with two of them exhibiting multiple interactions that significantly shorten the inter-planar distances in the solid-state structure. The rich photophysical properties exhibited by these molecules hold immense promise for future applications in sensors and optoelectronic devices. Two of the considered tetraalkynylated anthracenes comprising a D-π-A-π-D motif demonstrate solvatochromism and halochromism, with one of them showing a low bandgap of 1.79 eV. The remaining compounds demonstrate bandgaps in the range of 1.79-2.04 eV.
Metallated Graphynes as a New Class of Photofunctional 2D Organometallic Nanosheets
Huang, Bolong,Li, Jiahua,Sun, Jibin,Sun, Mingzi,Tang, Tianhong,Wang, Zhengping,Wong, Wai-Yeung,Xie, Zheng,Xu, Linli,Zhang, Hongyang,Zhang, Jianqi
supporting information, p. 11326 - 11334 (2021/04/09)
Two-dimensional (2D) nanomaterials are attracting much attention due to their excellent electronic and optical properties. Here, we report the first experimental preparation of two free-standing mercurated graphyne nanosheets via the interface-assisted bottom-up method, which integrates both the advantages of metal center and graphyne. The continuous large-area nanosheets derived from the chemical growth show the layered molecular structural arrangement, controllable thickness and enhanced π-conjugation, which result in their stable and outstanding broadband nonlinear saturable absorption (SA) properties (at both 532 and 1064 nm). The passively Q-switched (PQS) performances of these two nanosheets as the saturable absorbers are comparable to or higher than those of the state-of-the-art 2D nanomaterials (such as graphene, black phosphorus, MoS2, γ-graphyne, etc.). Our results illustrate that the two metallated graphynes could act not only as a new class of 2D carbon-rich materials, but also as inexpensive and easily available optoelectronic materials for device fabrication.
Optical and electrochemical effects of triarylamine inclusion to alkoxy BODIPY-based derivatives
Insuasty, Alberto,Madrid-Usuga, Duvalier,Mora-León, Ana G.,Ortiz, Alejandro,Rocha-Ortiz, Juan S.
, p. 18114 - 18123 (2021/10/12)
Three new triphenylamine-BODIPY dyadsBDPT1-3have been designed and synthesized. Their optoelectronic properties were investigated, which revealed strong electronic interactions between the donor and acceptor moieties, together with high sensitivity to the inclusion of alkoxy groups. The properties of the dyads were compared with those of reference compoundsAandBDP1, which exhibit broader absorption in the visible region as a result of the inclusion of donor groups and extended conjugation of the BODIPY core. Fluorescence quenching was also observed, which was attributed to the photoinduced electron transfer, evidenced from solvatochromic measurements, quantum yields and theoretical calculations. The oxidation potentials of new compounds were found to be lower when compared with those of other BODIPY analogues with donor groups attached. The redox, computational, absorbance and emission data suggest that compoundsBDPT1-3exhibit promising properties for their application in organic photovoltaic or light emitting (optoelectronic) devices.
ORGANIC ELECTROLUMINESCENCE ELEMENT AND MATERIAL
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Paragraph 0329-0330; 0364-0365, (2020/05/16)
PROBLEM TO BE SOLVED: To provide a phosphorescent metal complex emitting blue light, which shows a low drive voltage, high emission efficiency, high color purity of emission and a long emission life when used for an element, and to provide an organic electroluminescence element containing the above metal complex. SOLUTION: The present invention provides a compound represented by general formula (I): ML1mL2n, and an organic electroluminescence element containing the above compound. SELECTED DRAWING: Figure 1 COPYRIGHT: (C)2020,JPOandINPIT
Styryl-based compound and organic light emitting diode comprising the same
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Paragraph 0292; 0296-0298; 0445; 0449-0451, (2020/06/30)
A styryl-based compound represented by Formula 1 below is disclosed. An organic light-emitting diode including the styryl-based compound is also disclosed.
D-A type excited state proton transfer high-efficiency fluorescent material, and preparation method and application thereof
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Paragraph 0026-0032, (2020/05/05)
The invention belongs to the technical field of organic fluorescent materials, and discloses a D-A type excited state proton transfer high-efficiency fluorescent material, and a preparation method andan application thereof. The specific structure of the D-A type excited state proton transfer high-efficiency fluorescent material is shown in the specification. The method comprises the following steps: carrying out a Suzuki coupling reaction on triphenylamine-4-boronic acid pinacol ester and 4-bromo-2-((N-phenyl)-9,10-phenanthroimidazole)phenol in a catalytic system, and carrying out subsequenttreatment to obtain the organic small molecular fluorescent material with the D-A structure. The fluorescent material has efficient fluorescence quantum efficiency, and can improve the luminous efficiency of an OLED device; and the large delta ET2-T1 and the small delta ES1-T2 are helpful for T2 to jump to the reverse system of S1, so that the exciton utilization rate and the external quantum efficiency of the OLED device are improved. The method is simple. The application is an application f the fluorescent material in the organic light-emitting device.
