5-undec-10-en-1-yl-2,2’-bithiophene | 851298-60-7

• 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-undec-10-en-1-yl-2,2’-bithiophene
• 英文别名: 5-(10-undecen-1-yl)-2,2'-bithiophene；5-(10-undecenyl)-2,2'-bithiophene；11-(2,2'-bithien-5-yl)undecene；5-(10-Undecen-1-yl)-2,2-bithiophene；2-thiophen-2-yl-5-undec-10-enylthiophene
• CAS: 851298-60-7
• 化学式: C₁₉H₂₆S₂
• 分子量: 318.547
• InChiKey: IEXFJYKXMZNZPO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8
• 重原子数：
  21
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  56.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-undec-10-en-1-yl-2,2’-bithiophene 以 正己烷 、 甲苯 为溶剂， 生成 1,3-bis[11-(2,2’-bithien-5-yl)undecyl]-1,1,3,3-tetramethyldisiloxane
  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：

  2-溴噻吩 、 2-(undec-10-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89%的产率得到5-undec-10-en-1-yl-2,2’-bithiophene
  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

• Process for the production of linear organic thiophene-phenylene oligomers
  申请人：Kirchmeyer Stephan

  公开号：US20050098777A1

  公开（公告）日：2005-05-12

  The invention relates to a novel process for the production of linear organic thiophene-phenylene oligomers represented by the following general formula (I), The process involves reacting (e.g., by means of a Suzuki coupling reaction) a compound represented by the following general formula (II), with a formula represented by the following general formula (III), YAr m Y   (III) The reaction may be conducted optionally in the presence of catalysts, optionally in a solution and/or optionally at elevated temperature. The linear organic thiophene-phenylene oligomers of the present invention may be used to form semi-conductive coatings.

  本发明涉及一种新型的线性有机噻吩-苯基寡聚物的生产方法，该寡聚物由以下通式（I）表示。该方法涉及将以下通式（II）所表示的化合物通过Suzuki偶联反应等反应与以下通式（III）所表示的化合物反应，其中YArmY  （III）。该反应可以在催化剂的存在下、在溶液中或在高温下进行。本发明的线性有机噻吩-苯基寡聚物可用于形成半导体涂层。
• 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。
• Makromolekulare Verbindungen mit Kern-Schale-Struktur
  申请人：H.C. Starck GmbH

  公开号：EP1580217A1

  公开（公告）日：2005-09-28

  Die Erfindung betrifft makromolekulare Verbindungen mit einer Kern-Schale-Struktur, ein Verfahren zu deren Herstellung sowie ihre Verwendung als Halbleiter in elektronischen Bauelementen.

  本发明涉及具有核壳结构的高分子化合物、其生产工艺及其在电子元件中作为半导体的用途。
• Halbleitende Schichten enthaltend lineare organische Thiophen-Phenylen-Oligomere
  申请人：H.C. Starck GmbH

  公开号：EP1867651A1

  公开（公告）日：2007-12-19

  Die Erfindung betrifft neue halbleitende Schichten enthaltend lineare organische Thiophen-Phenylen-Oitgomere der allgemeinen Formel (I) wobei die Verbindungen gemäß Formel (I) unter Verwendung von Thiophen-Pinakoilnboronsäureestern hergestellt werden.

  本发明涉及含有通式(I)的线性有机噻吩-苯基邻构体的新型半导体层 其中，根据式（I）的化合物是用噻吩-联苯硼酸酯制备的。
• Asymmetrical linear organic oligomers
  申请人：Kirchmeyer Stephan

  公开号：US20050139822A1

  公开（公告）日：2005-06-30

  The invention relates to asymmetrical linear organic oligomers represented by the following formula (I), X—R 1 —[—Ar—] n —R 2 (I) in which n is from 4 to 10, Ar is for example an optionally substituted 2,5-thienylene group, R 1 is for example a C 10 -C 20 alkylene group, R 2 is for example a C 1 -C 12 alkyl group, and X is for example a vinyl group or an alkoxysilyl group. Also described is a process for the production of such organic oligomers, and semiconductors in electronic modules that include such organic oligomers.

  本发明涉及下式(I)所代表的不对称线性有机低聚物、 X-R 1 -[-Ar-]-[-Ar-] n -R 2 (I) 其中 n 为 4 至 10，Ar 例如为任选取代的 2,5-噻吩基团，R 1 例如是一个 C 10 -C 20 烯基，R 2 例如是 C 1 -C 12 烷基，X 是乙烯基或烷氧基硅基。此外，还介绍了生产这种有机低聚物的工艺，以及包括这种有机低聚物的电子模块中的半导体。