- Non-conjugated water/alcohol soluble polymers with different oxidation states of sulfide as cathode interlayers for high-performance polymer solar cells
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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
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Read Online
- Synthesis method of sulfoxide compound
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The invention discloses a method for preparing sulfoxide derivatives with industrial application value through substituted diaryl (heterocyclic aryl) and aryl (heterocyclic aryl) alkyl sulfide compounds. Under electrochemical reaction conditions, diaryl (heterocyclic aryl) and aryl (heterocyclic aryl) alkyl sulfide compounds which are wide in source and easy to prepare and have structural diversity are used as raw materials, lithium perchlorate (LiClO4) is used as an electrolyte, acetonitrile (CH3CN) is used as a solvent, and oxygen is used as an oxidizing agent to prepare the diaryl (heterocyclic aryl) and aryl (heterocyclic aryl) alkyl sulfoxide derivatives. Compared with reported preparation methods of sulfoxide derivatives, the preparation method disclosed by the invention is green, environment-friendly, safe, energy-saving, wide in substrate application range, good in compatibility of product functional groups, easy in obtaining of raw materials and simple and convenient to operate.
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Paragraph 0031-0033; 0047-0049
(2021/04/07)
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- Electrochemical Scalable Sulfoxidation of Sulfides with Molecular Oxygen and Water
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An efficient and chemoselective synthesis of sulfoxides through the electrooxidation of sulfides has been well developed. This protocol takes advantage of electricity as the terminal oxidant and of molecular oxygen and water as the oxygen atom sources. A variety of structurally diverse sulfoxide compounds are assembled in moderate to excellent yields. The scaled-up reactions at 6–20 mmol show the good practicability and application potential of this methodology. A possible free radical mechanism has been proposed to rationalize the reaction procedure.
- Cheng, Zhen,Gao, Xinglian,Yao, Lingling,Wei, Zhaoxin,Qin, Guohui,Zhang, Yonghong,Wang, Bin,Xia, Yu,Abdukader, Ablimit,Xue, Fei,Jin, Weiwei,Liu, Chenjiang
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p. 3743 - 3747
(2021/07/26)
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- Electrochemical oxygenation of sulfides with molecular oxygen or water: Switchable preparation of sulfoxides and sulfones
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A practical and eco-friendly method for the controllable aerobic oxygenation of sulfides by electrochemical catalysis was developed. The switchable preparation of sulfoxides and sulfones was effectively controlled by reaction time, in which both molecular oxygen and water can be used as the oxygen source under catalyst and external oxidant-free conditions. The electrochemical protocol features a broad substrate scope and excellent site selectivity and is successfully applied to the modification of some sulfide-containing pharmaceuticals and their derivatives. This journal is
- Li, Jin-Heng,Li, Yang,Sun, Qing,Xue, Qi,Zhang, Ting-Ting
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supporting information
p. 10314 - 10318
(2021/12/17)
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- Emodinas a novel organic photocatalyst for selective oxidation of sulfides under mild conditions
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Herein, we have developed naturally-occurringEmodin, which is commercially available at low-cost, as a novel organic photocatalyst for the first time.Emodinwas successfully employed in the selective oxidation of sulfides promoted by visible-light, deliver
- Li, Min,Lou, Jiangli,Rao, Yijian,Yuan, Zhenbo,Zhang, Yan
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p. 19747 - 19750
(2020/06/04)
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- Switchable Synthesis of Aryl Sulfones and Sulfoxides through Solvent-Promoted Oxidation of Sulfides with O2/Air
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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
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supporting information
p. 8925 - 8929
(2019/11/14)
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- Synthesis and nano-Pd catalyzed chemoselective oxidation of symmetrical and unsymmetrical sulfides
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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
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p. 3048 - 3055
(2019/03/21)
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- Method for synthesizing sulfoxide compound
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The invention discloses a method for synthesizing a sulfoxide compound and belongs to the technical field of synthesis of organic compounds. The method disclosed by the invention comprises the step of catalyzing a reaction between a thioether compound and an oxygen gas agent under the condition of illumination by taking perylene bisimide as a catalyst, thereby obtaining the sulfoxide compound. According to the method, selective oxidation of thioether catalyzed by perylene bisimide under visible light is achieved for the first time, and sulfoxide derivatives are successfully constructed in high yield; and according to the method, the reaction conditions are mild, the reaction efficiency is high, the substrate applicable range is wide, the atom utilization ratio is high, the regioselectivity and chemical selectivity of reaction are high, and thus, the method has a potential application value.
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Paragraph 0076-0078
(2019/10/04)
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- Cercosporin-bioinspired selective photooxidation reactions under mild conditions
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The development of an efficient system for selective oxidation of organic compounds to generate more valuable compounds with molecular oxygen is a significant challenge in industrial chemistry. Bioinspired by the ability of naturally occurring perylenequinonoid pigments (PQPs) to generate reactive oxygen species (ROS) upon photoirradiation, here we report that cercosporin, one of the perylenequinonoid pigments, can function as a cost-effective and environmentally friendly photocatalyst for a wide range of selective oxidations, including benzylic C-H bonds to carbonyls, amines to aldehydes, and sulfides to sulfoxides. All of the representative reactions proceeded smoothly with high efficiency under mild conditions. Owing to the use of inexpensive metal-free visible light-driven photocatalyst produced from microbial fermentation with cheap glucose as the starting material and the ease of handling, we expect that this developed method will be particularly attractive for many more applications in synthetic transformation.
- Li, Jia,Bao, Wenhao,Tang, Zhaocheng,Guo, Baodang,Zhang, Shiwei,Liu, Haili,Huang, Shuping,Zhang, Yan,Rao, Yijian
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supporting information
p. 6073 - 6081
(2019/11/20)
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- Visible-light photocatalytic aerobic oxidation of sulfides to sulfoxides with a perylene diimide photocatalyst
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Photosensitized oxygenation has been recognised as a modern method of incorporating oxygen into a substrate, as it offers environmentally benign alternatives to several conventional synthetic procedures. A metal-free aerobic selective sulfoxidation photos
- Gao, Yueying,Xu, Huan,Zhang, Shiwei,Zhang, Yan,Tang, Chunlei,Fan, Weizheng
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supporting information
p. 7144 - 7149
(2019/08/07)
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- Intramolecular Catalyst Transfer on a Variety of Functional Groups between Benzene Rings in a Suzuki–Miyaura Coupling Reaction
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Suzuki–Miyaura coupling reaction of BrC6H4-X-C6H4Br 1 (X=CH2, CO, N-Bu, O, S, SO, and SO2) with arylboronic acid 2 was investigated in the presence of tBu3PPd precatalyst and CsF
- Yokozawa, Tsutomu,Harada, Natsumi,Sugita, Hajime,Ohta, Yoshihiro
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supporting information
p. 10059 - 10062
(2019/07/17)
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- Desulfurization of Diaryl(heteroaryl) Sulfoxides with Benzyne
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Two benzyne-enabled desulfurization reactions have been demonstrated which convert diaryl sulfoxides and heteroaryl sulfoxides to biaryls and desulfurized heteroarenes, respectively. The reaction accessing biaryls tolerates a variety of functional groups, such as halides, pseudohalides, and carbonyls. Mechanistic studies reveal that both reactions proceed via a common assembly process but divergent disassemblies of the generated tetraaryl(heteroaryl) sulfuranes.
- Chen, De-Li,Sun, Yan,Chen, Mengyuan,Li, Xiaojin,Zhang, Lei,Huang, Xin,Bai, Yihui,Luo, Fang,Peng, Bo
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supporting information
(2019/06/13)
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- Redox-Neutral Synthesis of Selenoesters by Oxyarylation of Selenoalkynes under Mild Conditions
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An approach for the mild synthesis of selenoesters starting from selenoalkynes through an acid-catalyzed, redox-neutral oxyarylation reaction is reported. Br?nsted acid activation of a selenoalkyne leads to a selenium-stabilized vinyl cation, which is cap
- Baldassari, Lucas L.,Mantovani, Anderson C.,Senoner, Samuel,Maryasin, Boris,Maulide, Nuno,Lüdtke, Diogo S.
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supporting information
p. 5881 - 5885
(2018/09/25)
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- Enantioselective Synthesis of Chiral-at-Sulfur 1,2-Benzothiazines by CpxRhIII-Catalyzed C?H Functionalization of Sulfoximines
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Sulfoximines with stereogenic sulfur atoms are attractive structural motifs in drug discovery. A direct catalytic enantioselective method for the synthesis of sulfur-chiral 1,2-benzothiazines from readily accessible diaryl sulfoximines is presented. Rhodium(III) complexes equipped with chiral cyclopentadienyl ligands and paired with suitable carboxylic acid additives engage in an enantiodetermining C?H activation directed by the sulfoximine group. Subsequent trapping of the rhodacycle with a broad range of diazoketones gives access to S-chiral 1,2-benzothiazines with synthetically highly attractive substitution patterns in good yields and enantioselectivities.
- Sun, Yang,Cramer, Nicolai
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supporting information
p. 15539 - 15543
(2018/11/02)
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- No-carrier-added [18F]fluoroarenes from the radiofluorination of diaryl sulfoxides
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No-carrier-added [18F]fluoroarenes were synthesized through the radiofluorination of diaryl sulfoxides with [18F]fluoride ion. Diaryl sulfoxides bearing a para electron-withdrawing substituent readily gave the corresponding 4-[18F]fluoroarenes in high RCYs. This process broadens the scope for preparing novel 18F-labeling synthons and PET radiotracers.
- Chun, Joong-Hyun,Morse, Cheryl L.,Chin, Frederick T.,Pike, Victor W.
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supporting information
p. 2151 - 2153
(2013/03/14)
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- Polystyrene and silica gel-supported, AlCl3-catalyzed preparation of diaryl sulfoxides from arenes and thionyl chloride
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A simple, chemoselective, and efficient method has been developed for direct conversion of arenes to symmetrical diaryl sulfoxides using thionyl chloride in the presence of a catalytic amount of cross-linked polystyrene-supported aluminium chloride (Ps-AlCl3) and silica gel-supported aluminium chloride (SiO2-AlCl3). These solid acid catalysts are stable and can be easily recovered and reused without appreciable change in their efficiency. Copyright Taylor & Francis Group, LLC.
- Boroujeni, Kaveh Parvanak
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experimental part
p. 2085 - 2091
(2010/12/19)
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- Oxidation kinetics of some sulfoxides with N,N-dibromobenzene sulfonamide
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The kinetics of oxidation of some sulfoxides with dibromamine-B yielding sulfones was investigated in presence of HgII, and the rate equation, kobs = k3K2K′h[S]/[RNH 2] + K′h was found to be valid. The reaction involves two distinct pathways namely initial fast step and a subsequent slow step. The chloride ions have no effect on the reactivity of sulfoxides. Sulfoxides containing electron-attracting substituents retard the reactivity while those containing electron-releasing constituents accelerate the rate of oxidation. Exner plot confirms the operation of same mechanism in all the sulfoxides studied. Electrophilic addition of Br+ to sulfur atom results in an electron-deficient sulfonium centre which decomposes in a slow rate-limiting step. The rate coefficients are treated in terms of multiparametric extensions of the Hammett equation to have more insight into the mechanistic aspects.
- Meenakshisundaram, Subbiah,Amutha
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p. 679 - 682
(2008/09/18)
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- Lithium/Sodium Perchlorate Catalyzed Synthesis of Symmetrical Diaryl Sulfoxides
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Synthesis of diaryl sulfoxides from aromatics and thionyl chloride catalyzed by LiClO4/NaClO4 at room temperature is described. Mild reaction conditions, simple work-up, inexpensive and easily available catalysts are important and attractive features of this method.
- Bandgar,Makone
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p. 743 - 750
(2007/10/03)
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- Highly Rapid and Direct Synthesis of Diaryl Sulfoxides
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Aromatic compounds react smoothly with thionyl chloride in the presence of 10 mol% of water at ambient temperature to afford the corresponding symmetrical diaryl sulfoxides in good to excellent yields with high regioselectivity.
- Bandgar,Kinkar,Kamble,Bettigeri
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p. 2029 - 2032
(2007/10/03)
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- Trifluoromethanesulfonic acid catalyzed preparation of symmetrical diaryl sulfoxides from arenes and thionyl chloride
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The preparation of symmetrical diaryl sulfoxides from thionyl chloride and arenes catalyzed by trifluoromethanesulfonic acid is described. The reaction is characterized by its mildness, high yields, selectivity, and ease of workup.
- Olah, George A.,Marinez, Eric R.,Prakash, G. K. Surya
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p. 1397 - 1398
(2007/10/03)
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- Selectivity in the TiO2-mediated photocatalytic oxidation of thioethers
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The relative rates of photooxygenation of substituted diphenyl sulfides on irradiated TiO2 powders suspended in oxygenated acetonitrile correlate linearly with σ+, as is consistent with formation of a surface bound cation radical in the primary photoprocess. Substituted dibenzyl sulfides, in contrast, suffer C-S cleavage upon photocatalyzed oxidation. Factors disposing these reactions toward preferential sulfoxide formation or bond cleavage are discussed.
- Fox,Abdel-Wahab
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p. 4533 - 4536
(2007/10/02)
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