CAS: 88493-55-4; Alpha-Sexithiophene

该化合物是属于类寡头动物的有机化合物,其特征是其共生的硫苯环系统,该化合物由6个硫苯组成,以线状方式连接,有助于其扩大欧洲同系. -exiithieny 的表象具有显著的电子特性,使其对有机电子,特别是有机半导体和光电装置等应用感兴趣.该化合物通常显示有机溶剂的溶性良好,有利于其加工和融入各种材料.其光学特性包括紫外光谱的强吸收,并展示荧光,这有利于在发光装置的应用. 此外, -exientieny的结构性特性允许通过功能化来产生可耐养的金属特性,使其成为开发电子和光电子应用先进材料的研究对象.

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2-Iodothiophene 5,5'-diiodo-2,2-bithiophene 5-iodo-2,2':5'2-terthiophene 5,5''-diiodo-2,2':5',2"-terthiophene α-sexithiophene-5-carboxaldehyde

合成工艺路线路线简述

  • 合成目标产物 Alpha-Sexithiophene 主要起始原料 2,2'-Bithiophene
  • 1081-34-1 = 88493-55-4
    反应条件:1.1 Catalysts: Palladium Diacetate,(+/-)-Camphorsulfonic Acid,1-Propanesulfonic Acid,3-(Methylthio)-,Sodium Salt (1:1) Solvents: Acetic Acid1.2 Reagents: Quinone Solvents: Tetrahydrofuran; 12 H,60 °C
    标题:Oligothiophene Synthesis By A Distinct,General C-H Activation Mechanism: Electrophilic Concerted Metalation-Deprotonation (Ecmd)
    作者:Wang,Long; Et Al
    参考文献:Chemrxiv 日期:2019 卷标:1 页码:1-16]

    1081-34-1 = 88493-55-4
    反应条件:1.1 Reagents: Oxygen Catalysts: Palladium Chloride Solvents: Methanol,Acetonitrile,Water; Rt; 7 D,Rt
    标题:Bonding Self-Assembled,Compact Organophosphonate Monolayers To The Native Oxide Surface Of Silicon
    作者:Hanson,Eric L.; Et Al
    参考文献:Journal Of The American Chemical Society 日期:2003 卷标:125(51) 页码:16074-16080]

    94581-95-0 = 88493-55-4
    反应条件:1.1 Reagents: Potassium Fluoride,Bis(Pinacolato)Diborane Catalysts: [1,1′-Bis(Diphenylphosphino)Ferrocene]Dichloropalladium Solvents: Methanol,Toluene; Rt; 10 Min,70 °C
    标题:Solution-Phase Microwave-Assisted Synthesis Of Unsubstituted And Modified α-Quinque- And Sexithiophenes
    作者:Melucci,M.; Et Al
    参考文献:Journal Of Organic Chemistry 日期:2004 卷标:69(14) 页码:4821-4828]

    4805-22-5 + 3480-11-3 = 88493-55-4
    反应条件:1.1 Reagents: Magnesium Catalysts: Dichloro[1,1′-(1,3-Propanediyl)Bis[1,1-Diphenylphosphine-Kp]]Nickel Solvents: Diethyl Ether1.2 Reagents: Hydrochloric Acid Solvents: Water
    标题:A Convenient Synthesis Of 2,5-Thienylene Oligomers; Some Of Their Spectroscopic And Electrochemical Properties
    作者:Chiem Van Pham; Et Al
    参考文献:Phosphorus 日期:1989 卷标:46(3-4) 页码:153-68]

    4805-22-5 = 88493-55-4
    反应条件:1.1 Reagents: Butyllithium Solvents: Tetrahydrofuran,Hexane1.2 Reagents: Water2.1 Reagents: Magnesium Catalysts: Dichloro[1,1′-(1,3-Propanediyl)Bis[1,1-Diphenylphosphine-Kp]]Nickel Solvents: Diethyl Ether2.2 Reagents: Hydrochloric Acid Solvents: Water
    标题:A Convenient Synthesis Of 2,5-Thienylene Oligomers; Some Of Their Spectroscopic And Electrochemical Properties
    作者:Chiem Van Pham; Et Al
    参考文献:Phosphorus 日期:1989 卷标:46(3-4) 页码:153-68]

    1081-34-1 = 88493-55-4
    反应条件:1.1 Reagents: Quinone Catalysts: Camphorsulfonic Acid,Palladium Diacetate,1-Propanesulfonic Acid,3-(Methylthio)-,Sodium Salt (1:1) Solvents: Acetic Acid,Tetrahydrofuran; 12 H,60 °C
    标题:Oligothiophene Synthesis By A General C-H Activation Mechanism: Electrophilic Concerted Metalation-Deprotonation (E-Cmd)
    作者:Wang,Long; Et Al
    参考文献:Acs Catalysis 日期:2019 卷标:9(8) 页码:6821-6836]

    94581-95-0 = 88493-55-4
    反应条件:1.1 Reagents: Triphenylphosphine,Zinc,Nickel Dichloride Solvents: Dimethylformamide
    标题:Cu,Ni,And Pd Mediated Homocoupling Reactions In Biaryl Syntheses: The Ullmann Reaction
    作者:Nelson,Todd D.; Et Al
    参考文献:Organic Reactions (Hoboken 日期:2004 卷标:63]

    94581-95-0 = 88493-55-4
    反应条件:1.1 Reagents: Triphenylphosphine,Zinc,Nickel Dichloride Solvents: Dimethylformamide1.2 Solvents: Chlorobenzene
    标题:Preparation Of α-Quater-,α-Sexi-,And α-Octithiophenes
    作者:Nakayama,Juzo; Et Al
    参考文献:Heterocycles 日期:1987 卷标:26(7) 页码:1793-6]

    4805-22-5 + 124394-47-4 = 88493-55-4
    反应条件:1.1 Reagents: Dichloro[1,1′-(1,3-Propanediyl)Bis[1,1-Diphenylphosphine-Kp]]Nickel Solvents: Diethyl Ether,Tetrahydrofuran
    标题:Thiophene Oligomers: Synthesis And Characterization
    作者:Martinez,F.; Et Al
    参考文献:Molecular Crystals And Liquid Crystals 日期:1989 卷标:167 页码:227-32]

    492-97-7 = 88493-55-4
    反应条件:1.1 Reagents: Sodium Bicarbonate,Bromine Solvents: Chloroform2.1 Reagents: Magnesium Catalysts: Dichloro[1,1′-(1,3-Propanediyl)Bis[1,1-Diphenylphosphine-Kp]]Nickel Solvents: Diethyl Ether2.2 Reagents: Hydrochloric Acid Solvents: Water
    标题:A Convenient Synthesis Of 2,5-Thienylene Oligomers; Some Of Their Spectroscopic And Electrochemical Properties
    作者:Chiem Van Pham; Et Al
    参考文献:Phosphorus 日期:1989 卷标:46(3-4) 页码:153-68]

    1003-09-4 + 5713-61-1 = 88493-55-4
    反应条件:1.1 Catalysts: Dichloro[1,1′-(1,3-Propanediyl)Bis[1,1-Diphenylphosphine-Kp]]Nickel Solvents: Diethyl Ether1.2 Reagents: Hydrochloric Acid Solvents: Water2.1 Reagents: Sodium Bicarbonate,Bromine Solvents: Chloroform3.1 Reagents: Magnesium Catalysts: Dichloro[1,1′-(1,3-Propanediyl)Bis[1,1-Diphenylphosphine-Kp]]Nickel Solvents: Diethyl Ether3.2 Reagents: Hydrochloric Acid Solvents: Water
    标题:A Convenient Synthesis Of 2,5-Thienylene Oligomers; Some Of Their Spectroscopic And Electrochemical Properties
    作者:Chiem Van Pham; Et Al
    参考文献:Phosphorus 日期:1989 卷标:46(3-4) 页码:153-68]

    6165-68-0 + 3339-79-5 = 88493-55-4
    反应条件:1.1 Reagents: Alumina,Potassium Fluoride Catalysts: [1,1′-Bis(Diphenylphosphino)Ferrocene]Dichloropalladium; Rt; 5 Min2.1 Reagents: N-Bromosuccinimide Solvents: Dimethylformamide3.1 Reagents: Potassium Fluoride,Bis(Pinacolato)Diborane Catalysts: [1,1′-Bis(Diphenylphosphino)Ferrocene]Dichloropalladium Solvents: Methanol,Toluene; Rt; 10 Min,70 °C
    标题:Solution-Phase Microwave-Assisted Synthesis Of Unsubstituted And Modified α-Quinque- And Sexithiophenes
    作者:Melucci,M.; Et Al
    参考文献:Journal Of Organic Chemistry 日期:2004 卷标:69(14) 页码:4821-4828]

    492-97-7 = 88493-55-4 + 5632-29-1 + 113728-71-5
    反应条件:1.1 Reagents: Acetic Acid,2,2,2-Trifluoro-,Mercury(2+) Salt (2:1) Solvents: Benzene1.2 Reagents: Triethylamine Catalysts: Palladium Chloride1.3 Reagents: Acetic Acid,2,2,2-Trifluoro-,Mercury(2+) Salt (2:1)1.4 Reagents: Triethylamine Catalysts: Palladium Chloride
    标题:A Novel Approach To A One-Pot Synthesis Of Unsubstituted Oligo(α-Thiophenes)
    作者:Buzhansky,Ludmila; Et Al
    参考文献:Journal Of Organic Chemistry 日期:2002 卷标:67(21) 页码:7523-7525]

    = 88493-55-4 + 5632-29-1 + 113728-71-5
    反应条件:1.1 Reagents: Acetic Acid,2,2,2-Trifluoro-,Mercury(2+) Salt (2:1) Solvents: Benzene1.2 Reagents: Triethylamine Catalysts: Palladium Chloride1.3 Reagents: Acetic Acid,2,2,2-Trifluoro-,Mercury(2+) Salt (2:1)1.4 Reagents: Triethylamine Catalysts: Palladium Chloride1.5 Reagents: Acetic Acid,2,2,2-Trifluoro-,Mercury(2+) Salt (2:1)1.6 Reagents: Triethylamine Catalysts: Palladium Chloride
    标题:A Novel Approach To A One-Pot Synthesis Of Unsubstituted Oligo(α-Thiophenes)
    作者:Buzhansky,Ludmila; Et Al
    参考文献:Journal Of Organic Chemistry 日期:2002 卷标:67(21) 页码:7523-7525
📜2,2'-联二噻吩置于(1,1'-Bis(Diphenylphosphino)Ferrocene)Palladium(II) Dichloride Aluminum Oxide,Potassium Fluoride,N-溴代丁二酰亚胺(Nbs),N-碘代丁二酰亚胺,联硼酸频那醇酯体系中,用 甲醇,N,N-二甲基甲酰胺,甲苯 作为反应溶剂,化学反应 0.25H,反应生成 α-六噻吩
参考文献:溶液相微波辅助合成未取代和修饰的α-奎宁和六噻吩
标题:溶液相微波辅助合成未取代和修饰的α-奎宁和六噻吩
摘要:描述了在液相微波辐射下容易合成难溶的未取代和修饰的α-喹啉和六噻吩的方法.微波辐射的使用使得这些化合物可通过铃木交叉偶联反应在几分钟内以高收率制备.通过一锅法的硼化/ Suzuki反应在10分钟内获得未取代的六噻吩,根据非常简单的程序进行纯化,并以84%的产率分离.报道了显示液晶性质的两种新的甲基化喹啉和六噻吩的有效合成.还描述了一种新的微波辅助方法,该方法可将醛基封端的喹啉和六噻吩转化为相应的氰基衍生物.微波的使用扩展到了sonogashira偶联反应,发现在制备含炔间隔基的喹噻吩中非常有效.已报道并讨论了该化合物的电子和光学特性,以及未取代的喹噻吩的特性.
DOI:10.1021/jo035723Q

专利信息


专利号:US-2010279122-A1
优先权日:2006-08-16
标题:Benzimidazole, Benzoxazole and Benzothiazole Derivatives, Optical Film Comprising them and Method of Producing thereof
发明人：NOKEL ALEXEY; LAZAREV PAVEL I
权利人:CRYSOPTIX KK
摘要:The present invention is relates to the synthesis of predominantly planar heterocyclic organic compound and the manufacture of optical films based on these compounds. Said organic compound has the general structural formula where Het is a predominantly planar heterocyclic molecular system possessing hydrophilic properties; B is a binding group; p is the number in the range from 3 to 8; S is a group providing solubility of the organic compound; m is a number in the range from 0 to 8. Said organic compound is transparent for electromagnetic radiation in the visible spectral range from 400 to 700 nm, and a solution of the compound or a salt thereof is capable of forming a substantially transparent optical layer on a substrate, with the heterocyclic molecular planes oriented predominantly parallel to the substrate surface.

专利号:US-6825358-B2
优先权日:2000-07-12
标题 :Synthesis of soluble derivatives of sexithiophene and their use as the semiconducting channels in thin-film field-effect transistors
发明人：AFZALI-ARDAKANI ALI; BREEN TRICIA LYNN; KAGAN CHERIE RENEE
权利人:IBM
摘要:In accordance with the first object of this invention soluble derivatives of sexithiophene in which terminal carbons are substituted with various polar groups such as phosphonic esters, phosphonic acids, phosphonates, carboxylic acids, carboxylates, amines, amides, carbamates, and alcohols, each separated from the terminal thiophene rings by one or more methylene groups, are synthesized. An TFT device in accordance with the second objective of this invention employs films of the above sexithiophene derivatives as the semiconducting component. These organic semiconductors are dissolved in common organic solvents and applied to the surface of a substrate using inexpensive, low-temperature solution-based processing such as spin-coating, dip-coating, drop-casting, or microcontact printing.

专利号:US-8293140-B2
优先权日:2005-06-28
标题:Aligned nanostructured polymers
发明人：EPSTEIN ARTHUR J; CHIOU NAN-RONG; LEE LY JAMES; LU CHUNMENG
权利人:EPSTEIN ARTHUR J; CHIOU NAN-RONG; LEE LY JAMES; LU CHUNMENG; UNIV OHIO STATE RES FOUND
摘要:Novel, simple methods are presented directed to the synthesis of aligned nanofibers of polyaniline and substituted derivatives on a substrate. The production of these fibers is achieved via various methods by controlling the concentration of aniline monomer or substituted aniline derivatives or an oxidant in the reaction medium and maintaining said concentration at a level much lower than conventional polyaniline synthesis methods. Methods are disclosed relating to the use of a permeable membrane to control the release of a monomer and/or oxidant as well as a bulk polymerization method.

专利号:US-6414164-B1
优先权日:2000-07-12
标 题:Synthesis of soluble derivatives of sexithiophene and their use as the semiconducting channels in thin-film filed-effect transistors

专利号:US-2014114052-A1
优先权日:2012-10-22
标 题:Palladium Catalyzed Reactions Executed on Solid-Phase Peptide Synthesis Supports for the Production of Self-Assembling Peptides Embedded with Complex Organic Electronic Subunits

专利号:US-2015112044-A1
优先权日:2012-10-22
标题:Palladium Catalyzed Reactions Executed on Solid-Phase Peptide Synthesis Supports for the Production of Self-Assembling Peptides Embedded with Complex Organic Electronic Subunits

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合成参考文献


参考文献:10.1007/978-3-030-70358-5_11
摘要:Zhou Y, Hanson K. Electronically Coupled TTA-UC Solar Cells. 2021 Oct 14. In: Emerging Strategies to Reduce Transmission and Thermalization Losses in Solar Cells.
参考文献:10.1007/s42341-025-00691-z
摘要:Kwon H, Jeong W, Park H, Song YK, Lee J. From Electrostatic Field Modulation to Electrochemical Control: The Evolution of Organic Transistors for Next-Generation Electronics. Trans. Electr. Electron. Mater. 2026 Jan 06;27(2):217–42. doi: 10.1007/s42341-025-00691-z.
参考文献:10.1021/jp105227p
摘要:Tsai WW, Tevis ID, Tayi AS, Cui H, Stupp SI. Semiconducting nanowires from hairpin-shaped self-assembling sexithiophenes. J Phys Chem B. 2010 Nov 18;114(45):14778–86. doi: 10.1021/jp105227p.
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