5-hexyl-5’’’-(5-hexen-1-yl)-2,2’:5’,2’’:5’’,2’’’-quaterthiophene | 1245732-85-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 双噻吩和低聚噻吩
• 英文名称: 5-hexyl-5’’’-(5-hexen-1-yl)-2,2’:5’,2’’:5’’,2’’’-quaterthiophene
• 英文别名: 5-hexyl-5'''-(5-hexen-1-yl)-2,2':5',2'':5'',2'''-quaterthiophene；2-(5-Hex-5-enylthiophen-2-yl)-5-[5-(5-hexylthiophen-2-yl)thiophen-2-yl]thiophene
• CAS: 1245732-85-7
• 化学式: C₂₈H₃₂S₄
• 分子量: 496.826
• InChiKey: TWWQCHMOSDOXOA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.9
• 重原子数：
  32
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  113
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,1,3,3-四甲基二硅氧烷 、 5-hexyl-5’’’-(5-hexen-1-yl)-2,2’:5’,2’’:5’’,2’’’-quaterthiophene 在 铂(0)-1,3-二乙烯-1,1,3,3-四甲基二硅氧烷 作用下， 以 甲苯 为溶剂， 反应 5.0h， 以87%的产率得到1-[6-(5’’’-hexyl-2,2’:5’,2’’:5’’,2’’’-quaterthien-5-yl)hexyl]-1,1,3,3-tetramethyl-disiloxane
  参考文献：
  名称：

  新型线性和支化低聚噻吩有机硅多足体的合成和聚集行为

  摘要：

  描述了具有不同共轭长度、脂肪族间隔和末端取代基的低聚噻吩的直链和支链有机硅衍生物的合成。获得了共轭长度达7个噻吩环的可溶性化合物。报道了它们在稀溶液中的聚集、薄膜中的自组装和本体中的相行为。

  DOI：

  10.1002/ejoc.202101495
• 作为产物：
  描述：

  5''-bromo-5-hexyl-[2,2';5',2'']terthiophene 、 2-(hex-5-en-1-yl)thiophene 在 正丁基锂 、 MgBr₂*Et₂O 、 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以91%的产率得到5-hexyl-5’’’-(5-hexen-1-yl)-2,2’:5’,2’’:5’’,2’’’-quaterthiophene
  参考文献：
  名称：

  Synthesis of Monochlorosilyl Derivatives of Dialkyloligothiophenes for Self-Assembling Monolayer Field-Effect Transistors

  摘要：

  Unsymmetrical dimethylchlorosilyl-substituted alpha,alpha'-dialkylquater-, quinque-, and sexithiophenes were designed and successfully synthesized by a combination of Kumada and Suzuki cross-coupling reactions followed by hydrosilylation. Optimization possibilities of the hydrosilylation of low-soluble linear oligothiophenes by dimethylchlorosilane as well as the nonreactive byproducts formed are described. The molecular structures of the obtained dimethylchlorosilyl-functionalized oligothiophenes were proven by NMR and DCI MS techniques. These compounds were found to be stable and reactive enough, even in the presence of the nonreactive byproducts, to form semiconducting monolayers on dielectric hydroxylated SiO2 surfaces by self-assembly from solution. The semiconducting properties of these oligothiophene SAMs were as good as those of bulk oligothiophenes. This allowed the production of stable, even under ambient conditions, SAMFETs with a mobility of up to 0.04 cm(2)/(V s) and an on/off ratio up to 1 x 10(8).

  DOI：

  10.1021/om100139y

文献信息

• OLIGOMERIC COMPOUNDS WHICH FORM A SEMICONDUCTOR LAYER
  申请人：Meyer-Friedrichsen Timo

  公开号：US20090283723A1

  公开（公告）日：2009-11-19

  Oligomeric compounds of the general formula (M), mixtures thereof and electronic components containing the same: wherein L represents a linear conjugated oligomeric chain; wherein each R A and each R B independently represents a moiety selected from the group consisting of linear or branched C 2 -C 20 -alkylene radicals, C 3 -C 8 -cycloalkylene radicals, mono- or polyunsaturated C 2 -C 20 -alkenylene radicals, C 2 -C 20 -oxyalkylene radicals, C 2 -C 20 -aralkylene radicals or C 2 -C 20 -oligo- or C 2 -C 20 -polyether radicals; wherein X A and X B each independently represents a moiety selected from optionally substituted vinyl groups, chlorine, iodine, hydroxyl, alkoxy groups having 1 to 3 carbon atoms, alkoxysilyl groups, silyl groups, chlorosilyl groups, siloxane groups, carboxyl groups, methyl or ethyl carbonate groups, aldehyde groups, methylcarbonyl groups, amino groups, amido groups, sulphone groups, sulphonic acid groups, halosulphonyl groups, sulphonate groups, phosphonic acid groups, phosphonate groups, trichloromethyl, tribromomethyl, cyanate groups, isocyanate groups, thiocyanate groups, isothiocyanate groups, cyano groups, nitro groups and H; wherein each Y independently represents a moiety selected from an optionally substituted alkoxysilylene group, silylene group, chlorosilylene group, methylene group, dichloromethylene group, dibromomethylene group, divalent siloxane group, disiloxane group, carboxyl group, carbonate group, amino group, amido group, sulphate group, phosphonate group, phosphate group, borate group, S and O; and wherein n represents an integer of 1 to 10.

  通式为（M）的低聚化合物，其混合物和含有它们的电子元件： 其中，L代表线性共轭低聚链；RA和RB各自独立地表示从线性或支链C2-C20烷基基团，C3-C8环烷基基团，单烯或多烯C2-C20烯基基团，C2-C20氧烷基基团，C2-C20芳基基团或C2-C20寡聚或C2-C20聚醚基团中选择的基团；XA和XB各自独立地表示从可选取代的乙烯基、氯、碘、羟基、1至3个碳原子的烷氧基、烷氧基硅基、硅基、氯硅基、硅氧烷基、羧基、甲基或乙基碳酸酯基、醛基、甲基羰基基、氨基、酰胺基、砜基、磺酸基、卤代磺酰基、磺酸盐基、膦酸基、膦酸盐基、三氯甲基、三溴甲基、氰酸基、异氰酸基、硫氰酸基、硫代异氰酸基、氰基、硝基和氢中选择的基团；每个Y各自独立地表示从可选取代的烷氧基硅烷基、硅烷基、氯硅烷基、亚甲基、二氯亚甲基、二溴亚甲基、二价硅氧烷基、二硅氧烷基、羧基、碳酸酯基、氨基、酰胺基、硫酸盐基、膦酸盐基、磷酸盐基、硼酸盐基、S和O中选择的基团；n表示1至10的整数。
• Synthesis of Monochlorosilyl Derivatives of Dialkyloligothiophenes for Self-Assembling Monolayer Field-Effect Transistors
  作者：Sergei A. Ponomarenko、Oleg V. Borshchev、Timo Meyer-Friedrichsen、Alexandra P. Pleshkova、Sepas Setayesh、Edsger C. P. Smits、Simon G. J. Mathijssen、Dago M. de Leeuw、Stephan Kirchmeyer、Aziz M. Muzafarov

  DOI：10.1021/om100139y

  日期：2010.10.11

  Unsymmetrical dimethylchlorosilyl-substituted alpha,alpha'-dialkylquater-, quinque-, and sexithiophenes were designed and successfully synthesized by a combination of Kumada and Suzuki cross-coupling reactions followed by hydrosilylation. Optimization possibilities of the hydrosilylation of low-soluble linear oligothiophenes by dimethylchlorosilane as well as the nonreactive byproducts formed are described. The molecular structures of the obtained dimethylchlorosilyl-functionalized oligothiophenes were proven by NMR and DCI MS techniques. These compounds were found to be stable and reactive enough, even in the presence of the nonreactive byproducts, to form semiconducting monolayers on dielectric hydroxylated SiO2 surfaces by self-assembly from solution. The semiconducting properties of these oligothiophene SAMs were as good as those of bulk oligothiophenes. This allowed the production of stable, even under ambient conditions, SAMFETs with a mobility of up to 0.04 cm(2)/(V s) and an on/off ratio up to 1 x 10(8).
• Synthesis and Aggregation Behavior of Novel Linear and Branched Oligothiophene‐Containing Organosilicon Multipods
  作者：Marina S. Polinskaya、Yuriy N. Luponosov、Oleg V. Borshchev、Jochen Gülcher、Ulrich Ziener、Ahmed Mourran、Jingbo Wang、Mikhail I. Buzin、Aziz M. Muzafarov、Sergey A. Ponomarenko

  DOI：10.1002/ejoc.202101495

  日期：2022.4.21

  Synthesis of linear and branched organosilicon derivatives of oligothiophenes with different conjugation lengths, aliphatic spacers, and terminal substituents is described. Soluble compounds with the conjugation length up to 7 thiophene rings were obtained. Their aggregation in dilute solutions, self-assembly in thin films, and phase behavior in the bulk is reported.

  描述了具有不同共轭长度、脂肪族间隔和末端取代基的低聚噻吩的直链和支链有机硅衍生物的合成。获得了共轭长度达7个噻吩环的可溶性化合物。报道了它们在稀溶液中的聚集、薄膜中的自组装和本体中的相行为。