5-methoxy-2,2'-bithiophene | 163928-54-9

• 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-methoxy-2,2'-bithiophene
• 英文别名: 2-Methoxy-5-thiophen-2-ylthiophene
• CAS: 163928-54-9
• 化学式: C₉H₈OS₂
• 分子量: 196.294
• InChiKey: MXPGHPUYZODRFU-UHFFFAOYSA-N

物化性质

• 沸点：
  286.0±25.0 °C(Predicted)
• 密度：
  1.244±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  65.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-methoxy-2,2'-bithiophene 在 哌啶 、 正丁基锂 作用下， 以 乙醚 、 乙醇 、 正己烷 为溶剂， 生成 5-(2,2-dicyanovinyl)-5'-methoxy-2,2'-bithiophene
  参考文献：
  名称：

  5-烷氧基和5-氨基取代的2,2'-联噻吩的甲酰化，双氰基化和三氰基化

  摘要：

  几个供体-受体取代bithiophenes通过的官能化合成相应的5-烷氧基-或5- aminobithiophenes 1通过不同的方法：维尔斯迈尔甲酰化，金属化，随后用DMF，使用TCNE或Knoevenagel缩合从相应的5-开始直接tricyanovinylation反应反应的甲酰基衍生物1。

  DOI：

  10.1016/s0040-4020(03)00705-1
• 作为产物：
  描述：

  methyl 4-oxo-4-(2-thienyl)butanoate 在 劳森试剂 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以43%的产率得到5-methoxy-2,2'-bithiophene
  参考文献：
  名称：

  A Combination of Friedel-Crafts and Lawesson Reactions to 5-Substituted 2,2’-Bithiophenes

  摘要：

  DOI：

  10.3987/com-01-9249

文献信息

• SULFONIUM SALT, HEAT- OR PHOTO-ACID GENERATOR, HEAT- OR PHOTO-CURABLE COMPOSITION, AND CURED PRODUCT THEREOF
  申请人：SAN APRO LTD.

  公开号：US20190284134A1

  公开（公告）日：2019-09-19

  The sulfonium salt does not contain a toxic metal and exhibits higher cationic polymerization performance and crosslinking performance than a tetrakis(pentafluorophenyl)borate salt. The heat- or photo-acid generator contains the sulfonium salt. The sulfonium salt is formed of a sulfonium cation selected from a group represented by general formulas (1), (9), (10) and (11) described below and a gallate anion represented by formula (a). The heat- or photo-acid generator contains the sulfonium salt. The heat- or energy ray-curable composition contains the acid generator and a cationically polymerizable compound. A cured product can be obtained by curing the same.

  硫铵盐不含有毒金属，表现出比四(五氟苯基)硼酸盐更高的阳离子聚合性能和交联性能。热或光酸发生剂含有硫铵盐。硫铵盐由下面描述的通用公式(1)、(9)、(10)和(11)所代表的一组硫铵阳离子和由公式(a)代表的镓酸根阴离子形成。热或光酸发生剂含有硫铵盐。热或能量射线固化组合物含有酸发生剂和阳离子聚合性化合物。通过固化可以获得固化产品。
• Push–pull bithiophene azo-chromophores bearing thiazole and benzothiazole acceptor moieties: Synthesis and evaluation of their redox and nonlinear optical properties
  作者：M. Manuela M. Raposo、M. Cidália R. Castro、M. Belsley、A. Maurício C. Fonseca

  DOI：10.1016/j.dyepig.2011.05.007

  日期：2011.12

  systems can readily be tuned. Push–pull 5-thiazolylazo-5′-alkoxy-2,2′-bithiophenes exhibit the most promising redox and the solvatochromic properties and second-order nonlinear optical response. The redox and the optical properties also show notable variations for the different heterocyclic spacers and were also sensitive to the electronic acceptor strength of the (benzo)thiazolyldiazene moieties.

  三个系列的联噻吩偶氮染料官能用噻唑-2-基或苯并噻唑-2-基二氮烯受体部分使用2,2'-联噻吩，5-烷氧基-2,2'- bithiophenes通过偶氮偶合反应合成，5- N，N-二烷基氨基-2，2′-联噻吩和噻唑基-和苯并噻唑基重氮盐作为偶联组分。5-烷氧基-2,2'-联噻吩前体产生了5-噻唑基偶氮-5'-烷氧基-2,2'-联噻吩，而5- N，N-二烷基氨基-2,2'-联噻吩的偶氮偶合反应用噻唑基重氮盐得到4-噻唑基-偶氮-5- N，N-二烷基氨基-2,2'-联噻吩。对于2，2-联噻吩与噻唑基重氮盐观察到不同的反应行为，这产生了预期的偶氮染料以及几种芳基化产物。分别通过循环伏安法，热重分析（TGA）和超瑞利散射（HRS）评估了新型发色团的氧化还原行为，热稳定性和首次超极化性。通过改变噻唑基二氮杂受体在联噻吩系统上的位置，可以方便地调节供体-受体π-共轭体系的电化学行为以及光学（线性和非线
• Sulfonium salt, heat- or photo-acid generator, heat- or photo-curable composition, and cured product thereof
  申请人：SAN APRO LTD.

  公开号：US11370751B2

  公开（公告）日：2022-06-28

  The sulfonium salt does not contain a toxic metal and exhibits higher cationic polymerization performance and crosslinking performance than a tetrakis(pentafluorophenyl)borate salt. The heat- or photo-acid generator contains the sulfonium salt. The sulfonium salt is formed of a sulfonium cation selected from a group represented by general formulas (1), (9), (10) and (11) described below and a gallate anion represented by formula (a). The heat- or photo-acid generator contains the sulfonium salt. The heat- or energy ray-curable composition contains the acid generator and a cationically polymerizable compound. A cured product can be obtained by curing the same.

  锍盐不含有毒金属，与四(五氟苯基)硼酸盐相比，具有更高的阳离子聚合性能和交联性能。热酸或光酸发生器中含有锍盐。锍盐由选自下述通式 (1)、(9)、(10) 和 (11) 所代表的锍阳离子和由式 (a) 所代表的没食子酸阴离子组成。热或光固化酸发生器含有锍盐。热固化或能量射线固化组合物包含酸发生器和阳离子可聚合化合物。通过固化可得到固化产品。
• Synthesis and Solvatochromic Properties of Donor-Acceptor-Substituted Oligothiophenes
  作者：Franz Effenberger、Frank Wuerthner、Felix Steybe

  DOI：10.1021/jo00112a032

  日期：1995.4

  The Pd-catalyzed cross coupling reaction of electron donor-substituted thiophenes 1 with electron acceptor-substituted halothiophenes 2,10 via organozinc intermediates or organotin compounds 5 to give bi-, ter-, and quaterthiophenes 3, 4, 6, 8, 12, 13, and 14 is described. (Dimethylamino)-bithiophenes 8 with acceptor groups of varying reactivity were prepared via 5d in 60-80% yield, whereas bithiophenes 6d,e were obtained as a mixture with phenylthiophenes 7d,e. Symmetrical substituted byproducts 11 were formed in the conversion of 1b with bromothiophenes 10 via organozinc compounds yielding oligothiophenes 6b and 12. The ter- and quaterthiophenes 13 and 14 were isolated in about 50-70% yield. The electronic interactions between donor and acceptor end groups in the conjugated bithiophenes 3, 4, and 8 are expressed in the intensive and markedly solvatochromic CT transitions. The solvatochromic behavior of 3, 4, and 8 was determined by linear regression analyses of absorption maxima in 11 solvents, whereby bithiophene 3d was found to be a very appropriate indicator dye whose absorption wavenumbers ($) over bar nu(max)(3d) in aliphatic and dipolar aprotic and-on consideration of the polarizability correction term d delta-in aromatic and chlorinated solvents excellently correlate with the pi* values defined by Kamlet and Taft.
• 5′-Alkoxy-2,2′-bithiophene azo dyes: a novel promising series of NLO-chromophores
  作者：M. Manuela M. Raposo、Ana M.F.P. Ferreira、M. Belsley、João C.V.P. Moura

  DOI：10.1016/j.tet.2008.04.061

  日期：2008.6

  A series of bithienyl azo dyes have been prepared from their corresponding coupling components, 5-alkoxy-2,2'-bithiophenes. The solvatochromic behaviour of the compounds was investigated. The hyperpolarizabilities beta of derivatives 3-5 were measured using hyper-Rayleigh scattering and thermogravimetric analysis (TGA) was used to evaluate their thermal stability. The experimental results indicate that good nonlinearity-thermal stability is well balanced for azo-bithiophene NLO-chromophores 3-5 making them good candidates for NLO applications. (C) 2008 Elsevier Ltd. All rights reserved.