- Cationic Nitrogen-Doped Helical Nanographenes
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Herein, we report the design and synthesis of a series of novel cationic nitrogen-doped nanographenes (CNDNs) with nonplanar geometry and axial chirality. Single-crystal X-ray analysis reveals helical and cove-edged structures. Compared to their all-carbon analogues, the frontier orbitals of the CNDNs are energetically lower lying, with a reduced optical energy gap and greater electron-accepting behavior. Cyclic voltammetry shows all the derivatives to undergo quasireversible reductions. In situ spectroelectrochemical studies prove that, depending on the number of nitrogen dopants, either neutral radicals (one nitrogen dopant) or radical cations (two nitrogen dopants) are formed upon reduction. The concept of cationic nitrogen doping and introducing helicity into nanographenes paves the way for the design and synthesis of expanded nanographenes or even graphene nanoribbons with cationic nitrogen dopants.
- Xu, Kun,Fu, Yubin,Zhou, Youjia,Hennersdorf, Felix,Machata, Peter,Vincon, Ilka,Weigand, Jan J.,Popov, Alexey A.,Berger, Reinhard,Feng, Xinliang
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- Systematic energy band gap control of pyrene based donor-acceptor-donor molecules for efficient chemosensor
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We have successfully prepared a series of pyrene based donor-acceptor-donor (D-A-D) molecules, 1,6-bis[(N,N-p-(R)-diphenylamino)phenyl]pyrene (R = CN (Py-CN), F (Py-F), H (Py-H), Me (Py-Me), and OMe (Py-OMe)), containing N,N-bis(p-(R)-phenyl)aniline as an electron donor and pyrene as an electron acceptor by using the Suzuki-Miyaura cross-coupling reaction in good yield and fully characterized. By introducing various N,N-bis(p-(R)-phenyl)aniline derivatives with electron-donating or electron-withdrawing R groups, the energy band gaps of Py-R were systematically controlled and emission colors were efficiently tuned from blue to yellow (441–536 nm). Absorption spectra of all Py-R compounds showed intramolecular charge transfer (ICT) transitions in the range of 350–450 nm in the ground state. Solvent-dependent emission spectra confirmed the substituent dependence of charge transfer ability in the excited state. Then, the charge transfer tendencies by the substituents were quantitatively observed using the Lippert-Mataga equation. The HOMO and LUMO energy levels of synthesized Py-R compounds were found in the range of ?5.44 to ?5.97 eV and ?2.68 to ?2.97 eV respectively from cyclic voltammetry (CV) experimental. Theoretical studies were conducted using density functional theory (DFT) and time-dependent DFT (TD-DFT) calculations to provide a basis for interpreting experimental data. Experimental and calculated values were found to be well correlated with the Hammett constants (σpara) and confirmed that the energy band gap was systematically controlled by the substituent effect. Furthermore, pyrene based D-A-D compounds with controllable band gap were employed as selective chemosensors to detect nitro explosives, and especially Py-CN demonstrated efficient sensing ability for ortho-nitroaniline (o-NA) by fluorescence quenching strategy.
- Kim, So-Yeon,Kim, Min-Ji,Ahn, Mina,Lee, Kyeong-Min,Wee, Kyung-Ryang
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- Module-Patterned Polymerization towards Crystalline 2D sp2-Carbon Covalent Organic Framework Semiconductors
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Despite rapid progress over the past decade, most polycondensation systems even upon a small structural variation of the building units eventually result in amorphous polymers other than the desired crystalline covalent organic frameworks. This synthetic dilemma is a central and challenging issue of the field. Here we report a novel approach based on module-patterned polymerization to enable efficient and designed synthesis of crystalline porous polymeric frameworks. This strategy features a wide applicability to allow the use of various knots of different structures, enables polycondensation with diverse linkers, and develops a diversity of novel crystalline 2D polymers and frameworks, as demonstrated by using the C=C bond-formation polycondensation reaction. The new sp2-carbon frameworks are highly emissive and enable up-conversion luminescence, offer low band gap semiconductors with tunable band structures, and achieve ultrahigh charge mobilities close to theoretically predicted maxima.
- Jin, Enquan,Geng, Keyu,Fu, Shuai,Addicoat, Matthew A.,Zheng, Wenhao,Xie, Shuailei,Hu, Jun-Shan,Hou, Xudong,Wu, Xiao,Jiang, Qiuhong,Xu, Qing-Hua,Wang, Hai I.,Jiang, Donglin
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supporting information
(2022/01/13)
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- COMPOUND AND ORGANIC LIGHT EMITTING DEVICE COMPRISING THE SAME
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Of a typic a.a typa/a.sub .aβbetaβbetaβbetaβbetaβbetaβbetaβbetaβbetaβbetaβbeteqa/a a.sub .beteqa/a.sub 1. (by machine translation)
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Paragraph 0162-0166
(2019/11/29)
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- Organic light emitting compound and application thereof and organic electroluminescent device
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The invention relates to the field of organic electroluminescent devices, and discloses an organic luminescent compound and application thereof and an organic electroluminescent device. The compound has a structure shown in a formula (I). The organic luminescent compound can regulate and control the HOMO energy level and LUMO energy level of an organic electroluminescent material, and simultaneously the organic luminescent compound has higher fluorescence quantum yield, thereby improving the luminescent efficiency and prolonging the service life of the material.
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Paragraph 0156-0159
(2019/09/16)
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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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p. 24015 - 24024
(2019/08/13)
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- BISTRIAZINE COMPOUND AND METHOD FOR PRODUCING THE SAME, AND WAVELENGTH CONVERSION EMISSION FILM PREPARED THEREWITH
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PROBLEM TO BE SOLVED: To provide a wavelength conversion emission film prepared with an organic fluorescent material that has high workability, has a maximum absorption wavelength in an ultraviolet region, and emits visible light. SOLUTION: A wavelength conversion emission film contains a bistriazine compound represented by formula (1a) as a component (Ar1 is a C14-22 divalent fused-ring aromatic hydrocarbon group; R1-R5 independently represent H, C1-12 alkoxy or C1-12 alkylsulfanyl). SELECTED DRAWING: None COPYRIGHT: (C)2018,JPOandINPIT
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Paragraph 0169; 0170; 0171
(2018/10/16)
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- BORON CONTAINING ORGANIC/HYBRID SCINTILLATION MATERIALS FOR GAMMA AND NEUTRON DETECTION
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The invention is directed to a method for making a boron containing compound, a method for making a plastic scintillator and a method for forming a neutron detecting material, and the materials made therein. Methods of use are also disclosed.
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Paragraph 0096; 0097
(2016/07/27)
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- PYRENE DERIVATIVES AND ORGANIC ELECTROLUMINESCENT DEVICE COMPRISING THE SAME
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The present invention relates to a novel pyrene derivative and an organic electroluminescent device using the same. More specifically, the pyrene derivative, which has different substituted groups with a pyrene structure at the center, exhibits excellent light emitting properties due to having superior stability and high color purity. Also, the organic electroluminescent device using the pyrene derivative can be operated with low voltage and provide high efficiency, thereby being usefully used in a full color display.(2) Substrate(3) Positive electrode(4) Hole injection and transport layer(5) Fluorescent and phosphate light emitting layer(6) Hole inhibition layer(7) Electron injection and transport layer(8) Negative electrodeCOPYRIGHT KIPO 2015
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Paragraph 0155-0157
(2016/10/10)
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- Reversible "off-on" fluorescent probe for anions based on a facile two-component ensemble
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A specific fluorescent switch for anions was successfully constructed. The novel sensing switch is a two-component ensemble, which was combined using a water-soluble conjugated polyelectrolyte and a boronic acid functionalized pyridine salt. In the ensemble, the polyelectrolyte is used as a fluorescent signal unit, and the pyridine boronic acid acts as receptor and quencher. The two-component ensemble shows a fluorescence reversible "off-on" response toward cyanide and phosphate anions based on different binding ways. Furthermore, the facile design and construction of this ensemble presents a novel opportunity for obtaining an efficient and practical probe.
- Wang, Xiaoju,Feng, Liheng,Zhang, Liwei
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p. 318 - 323
(2013/03/29)
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- LEAVING SUBSTITUENT-CONTAINING COMPOUND, ORGANIC SEMICONDUCTOR MATERIAL FORMED THEREFROM, ORGANIC ELECTRONIC DEVICE, ORGANIC THIN-FILM TRANSISTOR AND DISPLAY DEVICE USING THE ORGANIC SEMICONDUCTOR MATERIAL, METHOD FOR PRODUCING FILM-LIKE PRODUCT, PI-ELECTRON CONJUGATED COMPOUND AND METHOD FOR PRODUCING THE PI-ELECTRON CONJUGATED COMPOUND
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A leaving substituent-containing compound represented by General Formula (I), wherein the leaving substituent-containing compound can be converted to a compound represented by General Formula (Ia) and a compound represented by General Formula (II), by applying energy to the leaving substituent-containing compound, in General Formulas (I), (Ia) and (II), X and Y each represent a hydrogen atom or a leaving substituent, where one of X and Y is the leaving substituent and the other is the hydrogen atom; Q2 to Q5 each represent a hydrogen atom, a halogen atom or a monovalent organic group; Q1 and Q6 each represent a hydrogen atom or a monovalent organic group other than the leaving substituent; and among the monovalent organic groups represented by Q1 to Q6, adjacent monovalent organic groups may be linked together to form a ring.
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Page/Page column 161-162
(2012/01/06)
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