- Synthesis, aggregation-induced emission properties and mechanofluorochromic behavior of sulfur connected bis(tetraphenylethene) luminogens
-
Three novel bis(tetraphenylethene) (BTPE) derivatives 1–3 were efficiently synthesized. All the materials exhibited aggregation-induced emission characteristics, and the dynamic light scattering measurments proved that the average diameter of the oxidised analogues 2 and 3 was less than that of the thioether precursor 1 due to the oxidation of the linking S-atom. Linking two tetraphenylethylenes via a sulfur atom with different oxidation states offered compounds which showed reversible mechanofluorochromic behavior. The crystal-to-amorphous phase conversion process was responsible for the mechanofluorochromism. Most notably, sulfone-based BTPE 3 presented polymorphism due to different packing modes, and the three observable morphologies could be interconverted.
- Wu, Jiang,Yin, Jun,Chen, Sheng,Xiao, Hongyan,Yan, Bin,Yang, Qin
-
-
Read Online
- Palladium-catalysed thioetherification of aryl and alkenyl iodides using 1,3,5-trithiane as sulfur source
-
Thioetherification reaction of aryl iodides catalysed by palladium(II) complexes in the presence of 1,3,5-trithiane as sulphur source is reported. The paper presents the first homogeneous catalytic application of 1,3,5-trithiane in synthesis. Detailed optimization steps, the frames of the novel reaction are described, as well as the limitations and the substrate scope are also demonstrated. Moderate to good thioether yields were achieved in the presence of various substituted iodobenzenes and some alkenyl iodides, using palladium-xantphos catalyst system. Competitive reactions in the presence of mixed substrates were also performed and mechanistic considerations were assumed.
- Kollár, László,Pongrácz, Péter,Rajat Rao, Yalamarti Venkat,Zugó, Alexandra
-
-
- Scalable electrochemical reduction of sulfoxides to sulfides
-
A scalable reduction of sulfoxides to sulfides in a sustainable way remains an unmet challenge. This report discloses an electrochemical reduction of sulfoxides on a large scale (>10 g) under mild reaction conditions. Sulfoxides are activated using a substoichiometric amount of the Lewis acid AlCl3, which could be regeneratedviaa combination of inexpensive aluminum anode with chloride anion. This deoxygenation process features a broad substrate scope, including acid-labile substrates and drug molecules.
- Kong, Zhenshuo,Pan, Chao,Li, Ming,Wen, Lirong,Guo, Weisi
-
supporting information
p. 2773 - 2777
(2021/04/21)
-
- Bipolar fluorophores based on intramolecular charge-transfer moieties of sulfone for nondoped deep blue solution-processed organic light-emitting diodes
-
Dipolar emitters exhibited excellent performance in organic light-emitting diode (OLED). However, these molecules had intramolecular charge-transfer (ICT) properties, which posed challenge to obtain deep blue emission. In this study, three fluorophores were designed by introducing carbazole and diphenylamine as electron donors and sulfone as electron acceptor due to their mild charge-accepting properties and twisted angles. These materials appeared almost in vertical angles of the dihedral configuration, and exhibited high thermal and electrochemical stability, suitable for solution-processed OLED. The solution-processed non-doped devices based on these three emitters were realized, where two emissions within the standard deep blue emission range were achieved with the Commission International e de l'Eclairage (CIE) coordinates of (0.16, 0.12) and (0.16, 0.15).
- Cao, Liang,Zhang, Lei,Wei, Qiang,Zhang, Jiasen,Chen, Dongjun,Wang, Sheng,Su, Shi-jian,Wang, Tao,Ge, Ziyi
-
-
- Solid-State C-S Coupling in Nickel Organochalcogenide Frameworks as a Route to Hierarchical Structure Transfer to Binary Nanomaterials
-
In this work, the transfer of the flexible and easily tunable hierarchical structure of nickel organochalcogenides to different binary Ni-based nanomaterials via selective coupling of organic units was developed. We suggested the use of substituted aryl groups in organosulfur ligands (SAr) as traceless structure-inducing units to prepare nanostructured materials. At the first step, it was shown that the slight variation of the type of SAr units and synthetic procedures allowed us to obtain nickel thiolates [Ni(SAr)2]n with diverse morphologies after a self-assembly process in solution. This feature opened the way for the synthesis of different nanomaterials from a single type of precursor using the phenomenon of direct transfer of morphology. This study revealed that various nickel thiolates undergo selective C-S coupling under high-temperature conditions with the formation of highly demanding nanostructured NiS particles and corresponding diaryl sulfides. The in situ oxidation of the formed nickel sulfide in the case of reaction in an air atmosphere provided another type of valuable nanomaterial, nickel oxide. The high selectivity of the transformation allowed the preservation of the initial organochalcogenide morphologies in the resulting products.
- Ananikov, Valentine P.,Degtyareva, Evgeniya S.,Galushko, Alexey S.,Kashin, Alexey S.
-
-
- Room temperature nickel-catalyzed cross-coupling of aryl-boronic acids with thiophenols: Synthesis of diarylsulfides
-
A NiCl2/2,2′-bipyridine-catalyzed cross-coupling of thiophenols with arylboronic acids has been developed for the synthesis of symmetric and unsymmetric diarylsulfides at room temperature and in air. This methodology is reliable and offers a mild and easy to operate process for the synthesis of arylthioethers, which are essential compounds with applications in the pharmaceutical and agricultural industries. This method avoids the use of expensive transition metals, such as Pd, Ir or Rh, sophisticated ligands and elevated temperatures. It also has a wide substrate scope (55 examples) and provides products in good to excellent yields (72-93%).
- Bhowmik, Amit,Fernandes, Rodney A.,Yadav, Mahesh
-
p. 2447 - 2458
(2020/04/15)
-
- Dechalcogenization of Aryl Dichalcogenides to Synthesize Aryl Chalcogenides via Copper Catalysis
-
An application for dechalcogenization of aryl dichalcogenides via copper catalysis to synthesize aryl chalcogenides is disclosed. This approach is highlighted by the practical conditions, broad substrate scope, and good functional group tolerance with several sensitive groups such as aldehyde, ketone, ester, amide, cyanide, alkene, nitro, and methylsulfonyl. Furthermore, the robustness of this methodology is depicted by the late-stage modification of estrone and synthesis of vortioxetine. Remarkably, synthesis of more challenging organic materials with large ring tension under milder conditions and synthesis of some halogen contained diaryl sulfides which could not be synthesized using metal-catalyzed coupling reactions of aryl halogen are successfully accomplished with this protocol.
- Cao, Fei,Chen, Jinhong,Deng, Jiedan,Deng, Xuemei,Hou, Yongsheng,Shao, Xiangfeng,Shi, Tao,Wang, Yongqiang,Wang, Zhen,Wu, Lingxi,Yang, Jinru,Yang, Yuhang
-
p. 2707 - 2712
(2020/03/11)
-
- Efficient hydrodeoxygenation of sulfoxides into sulfides under mild conditions using heterogeneous cobalt-molybdenum catalysts
-
Nitrogen-doped carbon-supported cobalt-molybdenum bimetallic catalysts (abbreviated as Co-Mo/NC) are active for the hydrodeoxygenation of sulfoxides to sulfides under mild conditions (25-80 °C and 10 bar H2), which represents the first example of the use of heterogeneous non-noble metal catalysts for this transformation. MoO3 with Lewis acid sites assists the hydrodeoxygenation of sulfoxides into sulfides by hydrogen over cobalt nanoparticles.
- Yao, Kaiyue,Yuan, Ziliang,Jin, Shiwei,Chi, Quan,Liu, Bing,Huang, Renjie,Zhang, Zehui
-
supporting information
p. 39 - 43
(2020/01/13)
-
- Symmetrical sulfur-containing wet processing type blue organic electroluminescent material as well as preparation method and application thereof
-
The invention provides a series of sulfone-containing symmetrical wet process type blue organic electroluminescent materials, which contain sulfones, substituted carbazoles, fluorenes, triphenylamines and derivatives thereof. By a symmetrical design, the electron transmission balance is adjusted; the solubility of molecules is increased by increasing a branched chain of an alkyl chain, wet processing is facilitated and the production cost is reduced. The series of electroluminescent materials relate to the field of electroluminescence, can emit blue and dark blue fluorescence, and can be applied to the fields of OLED (Organic Light Emitting Diode) lighting and OLED display. The material has a strong electron acceptor and a weaker electron donor, a large conjugated structure and a twisted and partially rigid planar structure, the intermolecular force is suppressed, the stability of a device is improved, and high level fluorescence quantum efficiency and blue light material are obtained.
- -
-
Paragraph 0047; 0052; 0059; 0060
(2019/10/01)
-
- Synthesis and nano-Pd catalyzed chemoselective oxidation of symmetrical and unsymmetrical sulfides
-
A highly chemoselective, efficient and nano-Pd catalyzed protocol for the rapid construction of sulfoxides and sulfones via the oxidation of symmetrical and unsymmetrical sulfides using H2O2 as an oxidant has been developed, respectively. The ready availability of starting materials, easy recovery and reutilization of the catalyst, wide substrate scope, and high yields make this protocol an attractive alternative. The process also involves the metal-free and microwave-promoted synthesis of symmetrical diarylsulfides, and FeCl3-mediated preparation of symmetrical diaryldisulfides through the reaction of arenediazonium tetrafluoroborates with Na2S·9H2O as a sulfur source. In addition, unsymmetrical sulfides were generated via the K2CO3-mediated reaction of arenediazonium tetrafluoroborates with symmetrical disulfides.
- Li, Xing,Du, Jia,Zhang, Yongli,Chang, Honghong,Gao, Wenchao,Wei, Wenlong
-
p. 3048 - 3055
(2019/03/21)
-
- Switchable Synthesis of Aryl Sulfones and Sulfoxides through Solvent-Promoted Oxidation of Sulfides with O2/Air
-
A practical and switchable method for the synthesis of aryl sulfones and sulfoxides via sulfide oxidation was developed. The chemoselectivities of products were simply controlled by reaction temperature using O2/air as the terminal oxidant and oxygen source. The broad substrate scope, easy realization of gram-scale production, and the simplification of a sulfide oxidation system render the strategy attractive and valuable.
- Cheng, Zhen,Sun, Pengchao,Tang, Ailing,Jin, Weiwei,Liu, Chenjiang
-
supporting information
p. 8925 - 8929
(2019/11/14)
-
- IAP inhibitor and its preparation and use (by machine translation)
-
The invention of formula (I) compound and its pharmaceutically acceptable salt. Such compounds can be used for inhibiting IAP, thus can be used for the treatment of the IAP-mediated diseases, such as cancer, autoimmune diseases, and viral diseases. The invention also relates to pharmaceutical compositions of such compounds, the method of preparing such compounds and the compound or pharmaceutical composition in preparation for the treatment of cancer by the IAP-mediated, autoimmune diseases, and viral diseases in the application. (by machine translation)
- -
-
Paragraph 0187-0189
(2018/03/24)
-
- Self-host organic light-emitting small molecule material and preparation method and application thereof
-
The invention discloses a self-host organic light-emitting small molecule material connected with a sulfur-containing non-conjugated unit by a carbonyl group, and increasing reaction sites by connecting benzene rings on two sides separately. The invention further discloses a preparation method and application of the self-host organic light-emitting small molecule material. The self-host organic light-emitting small molecule material disclosed by the invention realizes the intramolecular charge transfer function, and the sulfur-containing non-conjugate unit owned by the self-host organic light-emitting small molecule material can act as a part of a host to show high device performances in a simplified device structure. The self-host organic light-emitting small molecule material disclosed by the invention is simple in preparation method, and various target products are obtained through a series of simple reactions. Furthermore, the material disclosed by the invention is determined in molecular weight, single in structure, very high in decomposition temperature and lower in sublimation temperature, thereby being easily sublimated into a high-purity light-emitting material.
- -
-
Paragraph 0042; 0044; 0045; 0046
(2018/07/07)
-
- A double acceptor organic light-emitting small molecule material and its preparation method and application (by machine translation)
-
The invention discloses a double-receptor organic light-emitting small molecule material, in order to carbonyl with the sulfone by benzene ring connected to constitute a novel double-receptor backbone unit, each of the two sides is connected to a benzene ring in order to increase the reaction sites. The invention also disclosed the above-mentioned double-receptor organic light-emitting small molecule material preparation method and its application. The receptor of the present invention connected to the light-emitting material can realize the intra-molecular charge transfer function, and its bipolar transmission characteristic reduces the unipolar light-emitting material carrier is not the issue of balance, thus simplifying the device structure, and improve the performance of the device. The invention is simple to prepare, through a series of simple reaction, is obtained for all the target product. The molecular weight of the material is determined, a single structure, has very high decomposition temperature and lower the sublimation temperature of the, can be applied to the organic electroluminescent diode. (by machine translation)
- -
-
Paragraph 0043; 0045-0047
(2018/07/30)
-
- Copper-Catalyzed Production of Diaryl Sulfides Using Aryl Iodides and a Disilathiane
-
A disilathiane was found to be a novel S1 source for the copper-catalyzed synthesis of diaryl sulfides using aryl iodides. The reaction of iodoarenes and hexamethyldisilathiane, (Me 3 Si) 2 S, in the presence of a catalytic amount of CuI/1,10-phenanthroline provided various types of diaryl sulfides in good yields.
- Ogiwara, Yohei,Maeda, Hiromu,Sakai, Norio
-
supporting information
p. 655 - 657
(2017/11/29)
-
- Preparation and Characterization of Ni-Modified Graphene Oxide Complex as an Efficient Catalyst for the Synthesis of Sulfides via Reaction of Arylhalides with S8 or Thiourea
-
In this work, complex of Ni-modified graphene oxide was prepared and characterized using FT-IR spectroscopy, SEM, XRD, TGA and ICP-OES techniques. This compound used as an efficient and recoverable catalyst for the C–S coupling reaction using sulfur-transfer reagents (S8 or thiourea). The catalyst was easily separated using a simple filtration and reusable without significant loss of their catalytic efficiency.
- Ghafouri-Nejad, Raziyeh,Hajjami, Maryam,Nejat, Razieh
-
-
- Cu(ii)-catalyzed sulfide construction: both aryl groups utilization of intermolecular and intramolecular diaryliodonium salt
-
A sulfur-iodine exchange protocol of diaryliodonium salts with inorganic sulfur salt was developed. Both aryl groups in the diaryliodonium salt were fully exerted in this transformation. Five- to eight-membered sulfur-containing heterocycles were achieved. Note that [1]benzothieno-[3,2-b][1]benzothiophene (BTBT) (an organic field-effect transistor (OFET) material) and Zaltoprofen were efficiently established through this method.
- Wang, Ming,Wei, Jianpeng,Fan, Qiaoling,Jiang, Xuefeng
-
supporting information
p. 2918 - 2921
(2017/03/15)
-
- Iron-catalyzed carbon–sulfur bond formation: Atom-economic construction of thioethers with diaryliodonium salts
-
Diaryliodonium salts are characterized by poor atom economy with the formation of one equivalent of an iodoarene as waste. We have developed an atom-economic iron-catalyzed protocol for the synthesis of a variety of thioethers with diaryliodonium salts. Not only cyclic diaryliodonium salts but also linear diaryliodonium salts were found to perform well in the reactions.
- Liu, Li,Qiang, Jian,Bai, Shuhua,Li, Yang,Li, Jian
-
p. 2365 - 2371
(2017/09/30)
-
- Preparation method of 4,4'-dimercaptodiphenylsulfide
-
The invention relates to a preparation method of 4,4'-dimercaptodiphenylsulfide. The method comprises the following steps: by using diphenylsulfide as an initial raw material, carrying out halogenating reaction to obtain 4,4'-dihalodiphenylsulfide, carrying out reaction on the 4,4'-dihalodiphenylsulfide and a vulcanizing reagent, and carrying out hydrolysis to obtain the 4,4'-dimercaptodiphenylsulfide. The method provided by the invention is simple to operate, has the advantages of higher product purity, high safety of the reaction process, and low cost, and is suitable for industrial production. More importantly, the method provided by the invention avoids using abundant strong acids in the conventional preparation method, and prevents the abundant wastewater generated in the production process from severely polluting the environment.
- -
-
Paragraph 0038; 0039
(2016/12/01)
-
- Non-conjugated water/alcohol soluble polymers with different oxidation states of sulfide as cathode interlayers for high-performance polymer solar cells
-
A series of non-conjugated water/alcohol soluble copolymers containing diphenyl sulfide, diphenyl sulfoxide or diphenyl sulfone in the main chain were synthesized. The surfactant-like functionalities in side chains endow the polymers with outstanding solubility in highly polar solvents and excellent electron extraction abilities, while the limited conjugation length of main chains renders the polymers weak optical absorption. These unique characteristics make the polymers excellent cathode interfacial layers, which contribute to highly efficient polymer solar cells (PSCs) with power conversion efficiencies of 8-9%. More importantly, some of them can yield highly efficient PSCs in a relative large interlayer thickness range of 2-20 nm. The results suggest that these polymers are promising candidates for use as cathode interfacial layers in single-junction PSCs and as recombination layers in multi-junction PSCs.
- Liu, Xi,Xu, Rongguo,Duan, Chunhui,Huang, Fei,Cao, Yong
-
supporting information
p. 4288 - 4295
(2016/06/01)
-
- Diaryl thioether compound, and synthetic method and application thereof
-
The invention discloses a diaryl thioether compound, and a synthetic method and an application thereof. Various diaryl thioether compounds can be obtained through a reaction of a reaction raw material high iodine salt in dimethyl sulfoxide at 60-100DEG C under the action of an odorless sulfuration reagent, an alkali, a metal catalyst and a ligand for 3-12h. Sulfur is introduced in the later stage, so poisoning of sulfur to the metal catalyst and incompatibility of an oxidant in the early stage reaction are avoided; the above inorganic sulfur source is nontoxic and odorless; and two aryl groups in the high iodine salt are fully used, so the atom economy of the method is fully shown. The diaryl thioether compound prepared through the method can be further used to synthesize a photoelectric material BTBT and an anti-inflammatory drug zaltoprofen.
- -
-
Paragraph 0100-0104
(2018/02/04)
-
- Aryl diazonium salt and thioacetamide: A catalyst free, efficient blend of an inexpensive arylating agent with "s" surrogate for sulphide synthesis
-
Novel, facile C-S and S-S bond coupling reactions were achieved by using an aryl diazonium salt as an arylating agent and thioacetamide as a sulphur surrogate. The reaction proceeds smoothly at room temperature without using any transition metal catalyst, ligand or base. Aryl diazonium salts undergo rapid reactions with thioacetamide at room temperature to give the desired products in a much shorter period than the previously reported metal catalysed protocols.
- Bhojane, Jeevan Manohar,Sarode, Sachin Ashok,Nagarkar, Jayashreemilind
-
p. 90046 - 90050
(2016/10/07)
-
- Highly efficient and reusable polystyrene-supported copper(II) catalytic system for S-arylation of potassium thiocyanate by aryl halides in water
-
An inexpensive, efficient and environmentally friendly copper(II) catalyst supported on polystyrene was successfully synthesized and used as a heterogeneous catalyst for S-arylation of potassium thiocyanate by aryl halides. Also this catalyst could be recovered and reused several times without any noticeable decrease in its catalytic activity. Copyright
- Hajipour, Abdol R.,Jajarmi, Saeideh
-
p. 566 - 570
(2016/07/16)
-
- Novel organic semiconductor compound and organic light emitting device using the same
-
The present invention relates to a novel organic semiconductor compound, and an organic electroluminescent device using the same. More particularly, the organic semiconductor compound according to the present invention is an azasiline derivative with a rigid structure having an electron doner and an electron acceptor in the molecule, and can embody excellent oxidation stability and light emitting characteristics. The organic electroluminescent device using the same has a high purity blue color having high quantum efficiency. The organic semiconductor compound is represented by chemical formula 1.
- -
-
Paragraph 0189-0193
(2016/10/10)
-
- Synthesis of Thioethers Using Triethylamine-Activated Phosphorus Decasulfide (P410
-
The synthesis of thioethers in excellent yields was achieved under mild conditions via the displacement reaction of halogens by sulfur. The cross-reaction of 2-(α-bromoacetyl)thiophene with triethylamine-activated phosphorus decasulfide (Et3N-P2S5) was elaborated by utilizing DFT calculations.
- Turkoglu, Gulsen,Cinar, M. Emin,Ozturk, Turan
-
p. 3618 - 3624
(2016/10/17)
-
- D–π–A polysulfones for blue electroluminescence
-
Donor–π–acceptor type fluorene-based copolymers with a sulfone unit were designed and synthesized for application in efficient pure-blue light emitting. The electroluminescence behaviors of these copolymers were investigated by fabricating light-emitting diodes and electrochemical cell devices. The former device little functioned but the latter worked well. The electrochemical cell devices having a configuration of ITO/PEDOT:PSS/copolymer:ionic liquid/Al exhibited purplish blue electroluminescence with an emission maximum at 434 nm (CIE coordinates (x, y) = (0.17, 0.10)) measured at 7 V. The initial positive scan of the D–π–A polysulfone based light emitting electrochemical cell with a sweep rate of 0.1 V s?1 afforded a maximum luminance of 1080 cd m?2 with a current efficiency of 1.96 cd A?1 at an operating voltage of 12.5 V.
- Geng, ZhongMin,Sato, Go,Marumoto, Kazuhiro,Kijima, Masashi
-
p. 3454 - 3461
(2016/09/23)
-
- Melamine-(H2SO4)3/melamine-(HNO3)3 instead of H2SO4/HNO3: A safe system for the fast oxidation of thiols and sulfides under solvent-free conditions
-
Melamine reacted with neat sulfuric acid and fuming nitric acid readily to form two new organic solid acids, namely melamine-(H2SO4)3 and melamine-(HNO3)3. Mixture of them acts as a unique powerful system instead of a hazardous H2SO4/HNO3 system for the direct oxidation of thiols. Also, this system can oxidize the sulfides in the presence of a catalytic amount of KBr and few drops of water. This procedure offers advantages such as very low reaction time, simple work-up, excellent yield and matching with some green chemistry protocols.
- Chehardoli, Gholamabbas,Zolfigol, Mohammad Ali
-
p. 606 - 612
(2015/11/17)
-
- High Tg fluoranthene-based electron transport materials for organic light-emitting diodes
-
In this study, fluoranthene-based derivatives with a high thermal stability were synthesized for applications in organic electroluminescent devices. The two derivatives synthesized in this study, bis(4-(7,9,10-triphenylfluoranthen-8-yl)phenyl)sulfane (TPFDPS) and 2,8-bis(7,9,10-triphenylfluoranthen-8-yl)dibenzo[b,d]thiophene (TPFDBT), were characterized by cyclic voltammetry, differential scanning calorimetry (DSC) and thermogravimetric analysis (TGA). TPFDPS exhibits a high Tg of 210 °C while TPFDBT is crystalline in nature. Both the derivatives are thermally stable up to 500 °C. The charge transport studies reveal predominant electron transport properties. Subsequently, we fabricated blue OLEDs with 2-tert-butyl-9,10-bis-(β-naphthyl)-anthracene (TBADN) as the emitting layer to demonstrate the applications of these molecules as an electron transporting layer.
- Kumar, Shiv,Patil, Satish
-
p. 6351 - 6357
(2015/08/11)
-
- A simple, efficient and recyclable catalytic system for carbon-sulfur coupling of aryl halides with thioacetamide
-
The carbon-sulfur coupling reaction of aryl halides with thioacetamide using an MCM-41-immobilized bidentate nitrogen copper(I) complex [MCM-41-2N-CuI] as an efficient heterogeneous catalyst is described. Developed catalytic system is found to be effective for the coupling reaction of aryl halides with thioacetamide providing moderate to high yield of diaryl sulfides. This heterogeneous copper catalyst exhibits higher activity than CuI and can be recovered by a simple filtration of the reaction solution and reused for at least 10 consecutive trials without any decreases in activity.
- Cai, Mingzhong,Yao, Ruiya,Chen, Lin,Zhao, Hong
-
p. 349 - 354
(2015/01/09)
-
- Transition-metal-free acid-mediated synthesis of aryl sulfides from thiols and thioethers
-
The preparation of diaryl and alkyl aryl sulfides via acid-mediated coupling of thiols and thioethers with diaryliodonium salts is reported. The scope, limitations, and mechanism of the transformation are discussed.
- Wagner, Anna M.,Sanford, Melanie S.
-
p. 2263 - 2267
(2014/04/03)
-
- A simple and green synthesis of diaryl sulfides catalyzed by an MCM-41-immobilized copper(I) complex in neat water
-
The heterogeneous carbon-sulfur bond formation reaction of aryl iodides with potassium thiocyanate was achieved in neat water at 130 C by using 5 mol% MCM-41-immobilized bidentate nitrogen/CuCl complex [MCM-41-2N-CuCl] as catalyst and Cs2CO3 as base, yielding a variety of diaryl sulfides in moderate to high yields. This heterogeneous copper catalyst can be easily prepared by a simple two-step procedure from commercially available and cheap reagents and recovered by a simple filtration and reused for 10 cycles without loss of catalytic activity.
- Cai, Mingzhong,Xiao, Ruian,Yan, Tao,Zhao, Hong
-
-
- A copper-catalyzed synthesis of symmetrical diarylsulfanes
-
A room-temperature, copper-catalyzed synthesis of symmetrical diarylsulfanes has been developed. The reaction proceeds from aryl iodides and elemental sulfur (S8) by the action of copper(I) salts in the presence of N-ethyl-N-isopropylpropan-2-amine to afford the corresponding diarylsulfanes in good yields. Georg Thieme Verlag Stuttgart New York.
- Yavari, Issa,Ghazanfarpour-Darjani, Majid,Solgi, Yazdan
-
p. 1121 - 1123
(2014/05/20)
-
- Poly(spirobifluorene)s containing nonconjugated diphenylsulfone moiety: Toward blue emission through a weak charge transfer effect
-
Instead of conjugated dibenzothiophene-S,S-dioxide (DBTSO), we have introduced nonconjugated diphenylsulfone (DPSO) as the electron-deficient unit into the main chain of poly(spirobifluorene)s (PSFs). Because of the weaker electron affinity of DPSO relative to DBTSO, the charge transfer from the pendant 2,3,6,7-tetraoctyloxyfluorene to the main chain can be effectively prevented. Consequently, the resultant polymers containing DPSO moiety show pure blue emissions, which is different from DBTSO-based PSFs that exhibit undesired green emissions. With a single-layer device configuration, a peak luminous efficiency of 2.90 cd/A and a maximum luminescence of 14130 cd/m2 have been realized for the polymer PSFDPSO03. The corresponding CIE coordinates are (0.17, 0.18), nearly independent of the applied current density from 2 to 592 mA/cm2. These results indicate that tuning the electron affinity of the incorporated electron-deficient units is a very promising strategy to control the charge transfer strength for the development of blue-emitting PSFs with high efficiency and stability.
- Wang, Xuchao,Zhao, Lei,Shao, Shiyang,Ding, Junqiao,Wang, Lixiang,Jing, Xiabin,Wang, Fosong
-
p. 2907 - 2914
(2014/06/09)
-
- Thermally activated delayed fluorescence materials based on 3,6-di-tert-butyl-9-((phenylsulfonyl)phenyl)-9H-carbazoles
-
A series of bipolar materials for thermally activated delayed fluorescence based on 3,6-di-tert-butyl-9-((phenylsulfonyl)phenyl)-9H-carbazoles, is synthesized by Ulmann coupling reactions. In these materials, the 3,6-di-tert-butylcarbazole group is linked at the 3-, 4- position or 3′-, 4′- position of diphenyl sulfone. The effects of the conjugation connectivity on the electronic, photophysical and electrochemical properties of these materials, are studied by extensive UV-vis, fluorescence spectroscopic measurements, cyclic voltammetry and theoretical calculations as well as X-ray crystallographic analysis. The energy gap between singlet and triplet in these materials is tuned from 0.39 eV to 0.22 eV by manipulation of conjugation of the electron donor units.
- Huang, Bin,Qi, Qi,Jiang, Wei,Tang, Jinan,Liu, Yuanyuan,Fan, Wenjuan,Yin, Zhihui,Shi, Fachen,Ban, Xinxin,Xu, Huange,Sun, Yueming
-
p. 135 - 144
(2014/07/21)
-
- Carbazole/sulfone hybrid D-π-A-structured bipolar fluorophores for high-efficiency blue-violet electroluminescence
-
Based on a D-π-A structural strategy incorporating carbazole as a mild electron-donor and sulfone as an electron-acceptor with a π-conjugation- breaking feature, two novel blue-violet emitting materials (CzS1 and CzS2) were successfully designed and synthesized. The two compounds exhibit high-efficiency fluorescent emissions of intramolecular charge-transfer transition type, with impressively high quantum yields in both solution and film states. CIE y below 0.06 and excellent current/power efficiencies up to 1.89 cd A-1/1.58 lm W-1 were achieved with their corresponding nondoped devices. These performances currently represent the best results for OLEDs with CIEy 0.06. Moreover, single-carrier devices were also fabricated to demonstrate the bipolar characteristics as well as to understand the different electroluminescence performance of the two fluorophores.
- Ye, Jun,Chen, Zhan,Fung, Man-Keung,Zheng, Caijun,Ou, Xuemei,Zhang, Xiaohong,Yuan, Yi,Lee, Chun-Sing
-
p. 2630 - 2637
(2013/07/26)
-
- Novel efficient blue fluorophors with small singlet-triplet splitting: Hosts for highly efficient fluorescence and phosphorescence hybrid WOLEDs with simplified structure
-
The exact hosts for F-P hybrid WOLEDs have been first demonstrated following a new design strategy for blue fluorophors with small singlet-triplet splitting. Two novel compounds DPMC and DAPSF exhibit efficient blue fluorescence, high triplet energies and good conductivities. These merits allow us to use new simplified device designs to achieve high efficiency, slow efficiency roll-off and stable emission color. Copyright
- Zheng, Cai-Jun,Wang, Jing,Ye, Jun,Lo, Ming-Fai,Liu, Xiao-Ke,Fung, Man-Keung,Zhang, Xiao-Hong,Lee, Chun-Sing
-
p. 2205 - 2211
(2013/06/27)
-
- Cu-catalyzed synthesis of diaryl thioethers and S -cycles by reaction of aryl iodides with carbon disulfide in the presence of DBU
-
Diaryl thioethers and S-cycles were obtained on the basis of the copper-catalyzed reaction of carbon disulfide and aryl iodides in the presence of DBU. This reaction enables the one-pot synthesis of diaryl thioethers by employing cheap, available, and easy-to-handle carbon disulfide with aryl iodides. The reaction was successfully employed in the construction of sulfur-containing cyclic molecules.
- Zhao, Peng,Yin, Hang,Gao, Hongxin,Xi, Chanjuan
-
p. 5001 - 5006
(2013/06/27)
-
- Use of base control to provide high selectivity between diaryl thioether and diaryl disulfide for C-S coupling reactions of aryl halides and sulfur and a mechanistic study
-
Previous studies have reported that S-arylation produces diaryl disulfide when the precursors include sulfur powder and aryl halide using CuI as the catalyst. However, our research has revealed that the use of different bases in the above S-arylation process results in the coproduction of diarylsulfane and diaryldisulfane. In addition, we have demonstrated that the ratio of the two products can be controlled by selecting the alkalinity of the bases. 1H NMR spectra showed that diaryldisulfane was the first product, which became the reagent in a reaction with aryl halide to form diarylsulfane through CuI catalysis. Various aryl halides were tested to enhance the selectivity between diarylsulfane and diaryldisulfane using various different bases, leading to the following principles. A weak base, such as metal carbonate or acetate, results in the production of only diaryldisulfane; a strong base, such as metal hydroxide, results in the production of both diaryldisulfane and diarylsulfane. According to DFT calculations, hydroxide ions, which were exchanged for iodide and bonded with Cu, affected Cu electrons more strongly to reduce diaryl disulfide.
- Chen, Hsing-Ying,Peng, Wei-Te,Lee, Ying-Hsien,Chang, Yu-Lun,Chen, Yen-Jen,Lai, Yi-Chun,Jheng, Nai-Yuan,Chen, Hsuan-Ying
-
p. 5514 - 5522
(2013/11/06)
-
- Ionic liquid as base and phase transfer agent: A green protocol for the synthesis of diaryl sulphides in water
-
A basic ionic liquid, 1-methyl-3-butylimidazolium hydroxide, [BMIm]OH, acts as a base and phase transfer agent in the copper-catalysed ligand free S-arylation in water. A variety of iodo and bromoaryl compounds undergo coupling with aryl and heteroaryl thiols in presence of this ionic liquid in water to provide the corresponding diaryl/aryl-heteroaryl sulfides. The use of benign [BMIm]OH and water as reaction medium makes this procedure greener and cost effective.
- Kundu, Debasish,Ranu, Brindaban C.
-
p. 1761 - 1765
(2014/01/17)
-
- Microwave-assisted reaction of aryl diazonium fluoroborate and diaryl dichalcogenides in dimethyl carbonate: A general procedure for the synthesis of unsymmetrical diaryl chalcogenides
-
A convenient, general and efficient procedure for the synthesis of unsymmetrical diaryl chalcogenides has been developed by the reaction of aryl diazonium fluoroborates and diaryl dichalcogenides in the presence of zinc dust in dimethyl carbonate under microwave irradiation. The reactions of a wide range of substituted aryl diazonium fluoroborates and diaryl dichalcogenides have been addressed. The zinc dust is required for the cleavage of diaryl dichalcogenides. The products are obtained in high purity after fast column chromatography of the crude residue after evaporation of dimethyl carbonate. The Royal Society of Chemistry 2012.
- Kundu, Debasish,Ahammed, Sabir,Ranu, Brindaban C.
-
experimental part
p. 2024 - 2030
(2012/07/17)
-
- PHOTOACID GENERATORS
-
A photoacid generator compound has formula (I): [in-line-formulae]G+Z???(I)[/in-line-formulae] wherein G has formula (II): In formula (II), X is S or I, each R0 is commonly attached to X and is independently C1-30 alkyl; polycyclic or monocyclic C3-30 cycloalkyl; polycyclic or monocyclic C6-30 aryl; or a combination comprising at least one of the foregoing groups. G has a molecular weight greater than 263.4 g/mol, or less than 263.4 g/mol. One or more R0 groups are further attached to an adjacent R0 group, a is 2 or 3, wherein when X is I, a is 2, or when X is S, a is 2 or 3. Z in formula (I) comprises the anion of a sulfonic acid, a sulfonimide, or a sulfonamide. A photoresist and coated film also includes the photoacid generator, and a method of forming an electronic device uses the photoresist.
- -
-
-
- Copper-catalyzed chalcogenation of aryl iodides via reduction of chalcogen elements by aluminum or magnesium
-
Aluminum-induced copper-catalyzed coupling of aryl iodides with selenium or sulfur element could afford the corresponding diaryl selenides or sulfides in good yields. When magnesium chloride as an additive was employed, diaryl monoselenides and monosulfides were selectively obtained. On the contrary, the use of sodium carbonate produced diaryl diselenides and disulfides. The preparation of diaryl diselenides was necessary for magnesium as a reductant. Regrettably, tellurium was very low reactivity.
- Taniguchi, Nobukazu
-
p. 10510 - 10515,6
(2012/12/12)
-
- A highly efficient method for the copper-catalyzed selective synthesis of diaryl chalcogenides from easily available chalcogen sources
-
An efficient protocol for copper-catalyzed C-S or C-Se bond formation between aryl iodides and easily available chalcogen sources leading to diaryl chalcogenides is reported. A variety of symmetrical diaryl sulfides and diaryl selenides were synthesized in good to excellent yields. Unsymmetrical diaryl sulfides were also obtained in moderate yields from two different aryl iodides by a one-pot tandem process. This strategy was further successfully utilized for the synthesis of 2-phenylbenzo[b]thiophene and of [1]benzothieno[3,2-b] benzothiophene. A new Cu-catalyzed one-pot approach for the selective synthesis of symmetrical diaryl chalcogenides and unsymmetrical diarylsulfides with use of Na2S or Se as chalcogen sources has been developed. Copyright
- Li, Yaming,Nie, Caiping,Wang, Huifeng,Li, Xiaoying,Verpoort, Francis,Duan, Chunying
-
experimental part
p. 7331 - 7338
(2012/01/06)
-
- An efficient copper-catalyzed carbon-sulfur bond formation protocol in water
-
An efficient protocol of copper-catalyzed C-S bond formation between aryl halides and potassium thiocyanate leading to diaryl sulfides is reported. A variety of diaryl sulfides can be synthesized in good to excellent yields up to 94%.
- Ke, Fang,Qu, Yanyang,Jiang, Zhaoqiong,Li, Zhengkai,Wu, Di,Zhou, Xiangge
-
supporting information; experimental part
p. 454 - 457
(2011/04/15)
-
- Nano copper oxide catalyzed synthesis of symmetrical diaryl sulfides under ligand free conditions
-
Potassium thiocyanate acts as an efficient sulfur surrogate in C-S cross-coupling reactions mediated by recyclable copper oxide nanoparticles under ligand free conditions. This protocol avoids foul smelling thiols, for the synthesis of a variety of symmetrical diaryl sulfides, via the cross-coupling of different aryl halides with potassium thiocyanate, affording corresponding products in moderate to excellent yields.
- Reddy, K. Harsha Vardhan,Prakash, V. Reddy,Kumar, A. Ashwan,Kranthi,Nageswar
-
supporting information; experimental part
p. 886 - 891
(2011/09/21)
-
- Ligand-free copper-catalyzed synthesis of diaryl thioethers from aryl halides and thioacetamide
-
Diaryl thioethers can be prepared via a copper-catalyzed cross-coupling between aryl halides and thioacetamide using Cs2CO3 as a base and DMSO-H2O as a solvent at 120 °C. Georg Thieme Verlag Stuttgart - New York.
- Tao, Chuanzhou,Lv, Aifeng,Zhao, Nan,Yang, Shuai,Liu, Xiaolang,Zhou, Jian,Liu, Weiwei,Zhao, Jing
-
supporting information; experimental part
p. 134 - 138
(2011/03/22)
-
- Recyclable heterogeneous supported copper-catalyzed coupling of thiols with aryl halides: base-controlled differential arylthiolation of bromoiodobenzenes
-
Alumina-supported copper sulfate efficiently catalyzes the 5-arylation of aromatic, heteroaromatic and aliphatic thiols with aryl as well as heteroaryl halides under aerobic, ligand-free conditions. This protocol provides an easy access to a variety of thioethers as well as unsymmetrical bis-thioethers by base-controlled differential coupling of thiols with iodo- and bromo-substituents in an aromatic halide. The catalyst is inexpensive, non-air sensitive, environmentally friendly and recyclable.
- Bhadra, Sukalyan,Sreedhar, Bojja,Ranu, Brindaban C.
-
experimental part
p. 2369 - 2378
(2009/12/28)
-
- Flow-vacuum pyrolysis of polycyclic compounds. 251. Pyrolysis of some 3-mercapto-5-substituted-1,2,4-triazoles
-
The flow-vacuum pyrolysis (FVP) of the 3-mercapto-5-substituted-1,2,4- triazoles 5a-c, between 475°C - 750°C, at 2 mm Hg, in inert atmosphere (4mL/min argon flow rate) and quartz pyrolysis tube (60 cm length, 1 cm internal diameter, quartz chips filling 30 mm long) afforded a complex mixture with cyano-diphenyl-sulphones 12a-c and corresponding diphenylsulphones 13a-c as main products. The reaction products were identified by GC/MS. A radical mechanism is suggested in order to explain the formation of the main reaction products.
- Istrati, Daniela,Popescu, Angela,Mihaiescu, Dan,Saramet, Ioana,Bala?u, Mihaela C.
-
experimental part
p. 497 - 503
(2009/05/11)
-
- Mono- or dichalcogenation of aryl iodide with sulfur or selenium by copper catalyst and aluminum
-
The copper-catalyzed mono- or dichalcogenation of aryl halide with sulfur or selenium can be carried out with the addition of aluminum. This method takes advantage of two properties of both the insertion of copper into the chalcogen-chalcogen bond and the reductive ability of aluminum. Furthermore, the addition of MgCl2 or Na2CO3 enables the selective synthesis of diaryl monochalcogenides or disulfides. Georg Thieme Verlag Stuttgart.
- Taniguchi, Nobukazu
-
p. 1687 - 1690
(2007/10/03)
-