- A highly efficient purely organic room-temperature phosphorescence film based on a selenium-containing emitter for sensitive oxygen detection
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Developing purely organic room-temperature phosphorescence (RTP) materials with high phosphorescence efficiency in film states is important for their applications but remains a great challenge. Herein, a donor-acceptor type RTP molecule (SeX-CzPh) with 9H-selenoxanthen-9-one and 9-phenyl-9H-carbazole as the acceptor and donor units, respectively, is designed and synthesized.SeX-CzPhshows a high phosphorescence quantum yield of 44.3% in a doped polystyrene film at room temperature, which is 4-fold higher than that of its analogueTX-CzPhwith 9H-thioxanthene-9-one as the acceptor unit. The heavy selenium atom plays a key role in achieving high phosphorescence quantum yields, owing to the effective ISC process through strong spin-orbit coupling. Moreover, theSeX-CzPh-based oxygen film sensor exhibits a wide detection range (0-2.1 × 105ppm), a highKSV(1.27 × 10?4ppm?1) and a low detection limit (4.9 ppm). This work demonstrates that 9H-selenoxanthen-9-one is a promising building block for the rational design of highly efficient purely organic RTP materials.
- Han, Xianchao,Shu, Haiyang,Tong, Hui,Wang, Lixiang,Wang, Shuai,Wu, Xiaofu
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- A Thioxanthone Sensitizer with a Chiral Phosphoric Acid Binding Site: Properties and Applications in Visible Light-Mediated Cycloadditions
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A chiral phosphoric acid with a 2,2’-binaphthol core was prepared that displays two thioxanthone moieties at the 3,3’-position as light-harvesting antennas. Despite its relatively low triplet energy, the phosphoric acid was found to be an efficient catalyst for the enantioselective intermolecular [2+2] photocycloaddition of β-carboxyl-substituted cyclic enones (e.r. up to 93:7). Binding of the carboxylic acid to the sensitizer is suggested by NMR studies and by DFT calculations to occur by means of two hydrogen bonds. The binding event not only enables an enantioface differentiation but also modulates the triplet energy of the substrates.
- Pecho, Franziska,Zou, You-Quan,Gramüller, Johannes,Mori, Tadashi,Huber, Stefan M.,Bauer, Andreas,Gschwind, Ruth M.,Bach, Thorsten
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- Evaluating brominated thioxanthones as organo-photocatalysts
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Bromination of the widely used triplet sensitizer thioxanthone extends the absorption spectrum into the visible range with only minor loss of lowest triplet state energy (3?kcal/mol for di-bromination). Because of bromine substitution, a slight increase in triplet quantum yield was observed. The di-brominated derivative was effective as organo-photocatalyst in performing [2?+?2] cross-photocycloaddition of acrylimide-based compounds under visible light irradiation.
- Iyer, Akila,Clay, Anthony,Jockusch, Steffen,Sivaguru
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- Catalyst-Controlled Stereoselective Barton–Kellogg Olefination
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Overcrowded alkenes are expeditiously prepared by the versatile Barton–Kellogg olefination and have remarkable applications as functional molecules owing to their unique stereochemical features. The induced stereodynamics thereby enable the controlled motion of molecular switches and motors, while the high configurational stability prevents undesired isomeric scrambling. Bistricyclic aromatic enes are prototypical overcrowded alkenes with outstanding stereochemical properties, but their stereocontrolled preparation was thus far only feasible in stereospecific reactions and with chiral auxiliaries. Herein we report that direct catalyst control is achieved by a stereoselective Barton–Kellogg olefination with enantio- and diastereocontrol for various bistricyclic aromatic enes. Using Rh2(S-PTAD)4 as catalyst, several diazo compounds were selectively coupled with a thioketone to give one of the four anti-folded overcrowded alkene stereoisomers upon reduction. Complete stereodivergence was reached by catalyst control in combination with distinct thiirane reductions to provide all four stereoisomers with e.r. values of up to 99:1. We envision that this strategy will enable the synthesis of topologically unique overcrowded alkenes for functional materials, catalysis, energy- and electron transfer, and bioactive compounds.
- Schmidt, Tanno A.,Sparr, Christof
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p. 23911 - 23916
(2021/10/08)
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- Formation and Disproportionation of Xanthenols to Xanthenes and Xanthones and Their Use in Synthesis
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A facile and versatile strategy employing TiCl4-mediated cyclization followed by a Cannizzaro reaction has been developed for the synthesis of various xanthene derivatives. The reaction proceeded smoothly to afford both xanthenes/xanthones or their sulfur derivatives and tolerated a wide range of electronically diverse substrates. Using this methodology, pranoprofen was synthesized in three steps in 59% overall yield from commercially available starting materials.
- Shi, Zeyu,Chen, Si,Xiao, Qiong,Yin, Dali
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p. 3334 - 3343
(2021/02/05)
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- Calix[4]resorcinarene compound as well as preparation method and application thereof
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The invention discloses a Calix[4]resorcinarene compound as well as a preparation method and application thereof, and further provides a starlike light-emitting material taking Calix[4]resorcinarene (CRA) as a core and application of the light-emitting material in an organic light-emitting diode. The synthesis method for the compound is simple, the reaction conditions are mild, and the yield is high; and particularly, the core CRA (Calix[4]resorcinarene) has eight high-reactive sites, the eight high-reactive sites can be connected to eight functional groups in a hung mode, and the corresponding functional compound has relatively good film-forming property and solubility and relatively high thermal stability. The compound is applied to the organic light-emitting diode as a light-emitting layer material, so that the excellent device performance can be achieved.
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Paragraph 0090; 0098-0101
(2019/04/02)
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- Highly efficient deep-blue OLEDs based on hybridized local and charge-transfer emitters bearing pyrene as the structural unit
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A new family of hybridized local and charge-transfer (HLCT) emitters bearing a pyrene structural unit has been developed. Deep-blue OLEDs based on them achieved high brightness over 10000 cd m-2, high maximum external quantum efficiency over 10.5%, and high maximum exciton utilization efficiency approaching 100%, with CIE coordinates of (0.152, 0.065).
- Fu, Caixia,Luo, Shuai,Li, Zhenzhen,Ai, Xin,Pang, Zhenguo,Li, Chuan,Chen, Kuan,Zhou, Liang,Li, Feng,Huang, Yan,Lu, Zhiyun
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supporting information
p. 6317 - 6320
(2019/06/07)
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- Compound, light-emitting material, device and display device
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The invention relates to the technical field of organic electroluminescent materials and particularly relates to a compound, a light-emitting material, a device and a display device. The compound hasa structure expressed by a formula which is as shown in the description. The compound can be used as a thermally activated delayed fluorescent (TADF) material. When the compound is used as a light-emitting material or a main body material of a light-emitting layer of an organic light-emitting device, the compound can achieve high light-emitting efficiency.
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Paragraph 0189-0190
(2018/09/08)
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- Compound and organic luminescence display device
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The invention relates to the technical field of organic electroluminescent materials, in particular to a compound and an organic luminescence display device. The compound has a structure shown by formula (I) in the description, wherein D represents an electron donor unit; A represents an electron receiver unit; m and n are respectively and independently selected from 1, 2 or 3; in addition, the sum of the m and the n is smaller than or equal to 4. When the compound is used as a luminous material, an object material or a main body material of the organic luminescence display device, high luminescence efficiency can be realized.
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Paragraph 0134-0136
(2018/10/19)
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- Aromatic heterocyclic compound and organic light-emitting display device
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The invention relates to an aromatic heterocyclic compound having a thermal active delay fluorescence (TADF) property, having a structure represented by a formula (I), wherein X1 and X2 are selected from S or O respectively; D represents a chemical group as an electron donor, and A represents a chemical group as an electron acceptor; m represents the number of electron donors D linked to the formula (I), and the electron donors D are the same or different; n represents the number of the electron acceptors linked to the formula (I), and the electron acceptors A are the same or different; m andn are 1 or 2 independently. The luminescence mechanism of the aromatic heterocyclic compound disclosed by the invention is thermal active delay fluorescence, and therefore high luminescence efficiencyis achieved. When the compound is used as a luminescent material, a luminescent host material or an object material in an organic light-emitting display device, the luminescent efficiency of the organic light-emitting display device can be improved, and the advantages of lower cost and longer service life are achieved.
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Paragraph 0113; 0114; 0115; 0116
(2018/11/22)
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- Aromatic compound and organic light-emitting display device
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The invention relates to an aromatic compound having thermally activated delayed fluorescence (TADF) properties. The aromatic compound has a structure of formula (I), wherein D is an electron donor; Ais an electron acceptor; R10 and R20 each is cycloalkyl; m and n are respectively the number of electron donors D and electron acceptors A attached to formula (I); d and e are respectively the numberof substituents R10 and R20; f is the number of parent nuclear phenyls; f is 1 or 2; d and e are respectively 1 or 2; m and n are respectively 1, 2 or 3; when f = 1, m + n + d + e is less than or equal to 6; and when f = 2, m + n + d + e is less than or equal to 10. The aromatic compound provided by the invention has a light-emitting mechanism of TADF, has high light-emitting efficiency, can increase the light-emitting efficiency of an organic light-emitting display device when the aromatic compound is as a light-emitting material, a light-emitting subject material or object material appliedto the organic light-emitting display device, and has the advantages of relatively low cost and longer service life. The invention also provides the organic light-emitting display device.
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Paragraph 0103-0107
(2019/01/08)
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- Thioxanthone compound crystal having room temperature phosphorescent property and preparation method and use thereof
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The present invention relates to a thioxanthone compound crystal having a room temperature phosphorescent property and a structure represented by the following formula I and a preparation method and use thereof, wherein R is-Cl,-Br,-OCH3, or-OCH(CH3)2. The crystal can be used as a room temperature phosphorescent material for optoelectronic devices (including light-emitting devices, display and illumination systems, organic electroluminescent devices, and the like), photocatalytic reactions, optical storage (information storage), molecular sensing, anti-counterfeiting and biological imaging andother optoelectronic fields.
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Paragraph 0057-0059
(2018/07/30)
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- Derivative of five-membered ring fused unit containing thioxanthene and preparation method and application of derivative
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The invention belongs to the field of organic optoelectronics, and discloses a derivative of a five-membered ring fused unit containing thioxanthene and a preparation method and application of the derivative. The chemical structural formula of the derivative of the five-membered ring fused unit containing the thioxanthene meets one of the general formulas shown in the description. Accordingly, themolecular structure becomes larger through a ring closing reaction, the high molecule rigidity is achieved, the thermostability of molecules is improved conveniently, the five-membered ring fused structure formed by ring closure makes conjugation enhanced, the carrier transport performance can be improved, the derivative serves as phosphor main materials, organic light-emitting diodes are prepared through evaporation, and the device performance can be improved.
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Paragraph 0078; 0080; 0081; 0091
(2018/07/15)
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- Preparation method of LED excitable sulfonium salts using thioxanthone as conjugated structure and application of preparation method
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The invention relates to a preparation method of LED excitable sulfonium salts using thioxanthone as a conjugated structure and application of the preparation method. A biphenyls structure is introduced on a thioxanthone structure, the absorption wavelength of molecules extends to a near ultraviolet-visible light region, and therefore, LED excitable sulfonium salts photoacid generator molecules are commercialized. The synthesis steps of the photoacid generator are simple, the photoacid generator is easy to purify, the cost is low, and the yield is high. The photoacid generator is an LED excitable photoacid generator, is wide in adaptable wavelength, has good light absorbing property in the ultraviolet-visible light region, and is suitable for light initiated polymerization from an ultraviolet region to a visible light region. In addition, when in an environment away from light, the photoacid generator can be stored for a long time, and the chemical stability is high. The LED excitable sulfonium salts have huge application value in an LED excitable ultraviolet-visible light initiation system.
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Paragraph 0031; 0032; 0030
(2017/09/13)
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- Synthesis of Chiral Thiourea-Thioxanthone Hybrids
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Four different 1-aminocyclohexanes bearing a tethered thioxanthone group in the 2-position were prepared. The synthesis commenced with the respective N-protected β-amino acids, the carboxyl group of which was employed for the introduction of the thioxanthone moiety. After construction of the thioxanthone and protecting group removal, the conversion of the amino group into the respective thiourea was accomplished by treatment with N -3,5-bis(trifluoromethyl)phenyl isothiocyanate and yielded the title compounds in which the thioxanthone resides in different spatial positions relative to the thiourea motif. Overall yields varied between 20-35%.
- Mayr, Florian,Mohr, Lisa-Marie,Rodriguez, Elsa,Bach, Thorsten
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p. 5238 - 5250
(2017/10/30)
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