3',4'-Diphenyl-2,2':5',2''-terthiophene

• 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: 3',4'-Diphenyl-2,2':5',2''-terthiophene
• 英文别名: 3,4-Diphenyl-2,5-dithiophen-2-ylthiophene
• 化学式: C₂₄H₁₆S₃
• 分子量: 400.589
• InChiKey: UTIJMWTVDWEWNP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  84.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  二氧化碳 、 3',4'-Diphenyl-2,2':5',2''-terthiophene 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.0h， 以87%的产率得到3',4'-diphenyl-2,2':5',2''-terthiophene-5,5''-dicarboxylic acid
  参考文献：
  名称：

  Synthesis, Structure, and Magnetic Properties of Bithiophene- and Terthiophene-Linked Manganese Metal–Organic Frameworks

  摘要：

  A series of metal-organic frameworks (MOFs) containing manganese centers and oligothiophene dicarboxylate linkers have been synthesized: [Mn(3PhT(2)DC)(DMF)(0.4)s(F12.0)2..s5.1.5 5DMF] (1), [Mn6(3F1T2PC)6. (DMF)3(-120)5"xDMF"YH20] (2), [Mn(T3DC)(H20)2] (3), [Mn(T3DC)(H20)1.3] (4), and [Mn(Ph2T3DC)(DMF)2] (5) (H23PhT2DC = 3,3'-dipheny1-2,2-bithiophene-5,5'-dicarboxylic acid; H23HT2DC:= 3,3'-dihexy1-2,2'bithiophene-5,5'-dicarboxylic acid; H2T3DC = 2,2':5',2"".ter,thiophene-5,5 '-dicarboxylic acid; H2Ph2T3DC = 3',4'-dipheny1-2,2':5',2"-terthiophene-5,5"-dicarboxylic acid, DMF = N,N-dimethylformamide). Compound 1 exists as a 2D sheet, 2-4 are 3D frameworks, and 5 is a ID chain. Compounds 3 and 4 are " isomers, and 3-5 are the first examples of crystallographically characterized terthiophene coordination polymers. In the case of 1, 2, and 5, the extended structure is sensitive to beta substitution of the oligothiophene linkers. Compounds 1-3 and S show antiferromagnetic behavior with typical values of g and J, and 3 exhibits a spin canting transition at 40 K.

  DOI：

  10.1021/ic401305c
• 作为产物：
  描述：

  硫化双(苯甲酰甲基) 在 四(三苯基膦)钯 溴 、 四氯化钛 、 potassium carbonate 、 锌 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 3',4'-Diphenyl-2,2':5',2''-terthiophene
  参考文献：
  名称：

  使用Br 2一锅氧化和溴化3,4-二芳基-2,5-二氢噻吩：3,4-二芳基-2,5-二溴噻吩的合成和应用

  摘要：

  通过3,4-二芳基-2,5-二氢噻吩与Br 2试剂的一锅反应以优异的收率（83-92 ）合成了一类3,4-二芳基-2,5-二溴噻吩（1b - 5b）％）。发现Br 2在3，4-二芳基-2，5-二氢噻吩转化为3，4-二芳基-2，5-二溴噻吩的过程中​​具有双重功能（氧化和溴化）。还研究了3,4-二芳基-2,5-二溴噻吩作为建筑材料的应用。以3,4-二苯基-2,5-二溴噻吩（1b）为模板，通过Suzuki偶联反应制备了2,3,4,5-四芳基噻吩类。这为制备2,3,4,5-四芳基噻吩提供了一种新的简单方法。

  DOI：

  10.1021/jo071172i

文献信息

• Synthesis, characterization, and electrogenerated chemiluminescence of phenyl-substituted, phenyl-annulated, and spirofluorenyl-bridged oligothiophenes
  作者：Ullrich Mitschke、Peter Bäuerle

  DOI：10.1039/b006553f

  日期：——

  To overcome the insolubility of higher oligothiophenes and simultaneously to enhance their processability with respect to an application in molecularly doped organic light-emitting devices (OLEDs) we synthesized phenyl-substituted, phenyl-annulated, and spirofluorenyl-bridged oligothiophenes 1–5. Significantly improved solubilities in polar solvents of up to three orders of magnitude were found and their optical and electrochemical properties were investigated in solution. Reflecting small conformational changes and the almost complete electronic separation of the substituents, phenyl substitution and the introduction of a spiro core by bridging the central bithienyl unit only slightly affected optical and redox properties in comparison to the unmodified oligothiophenes (6–8). In contrast, the presence of an isothianaphthene (benzo[c]thiophene) unit in the oligomeric chain led to a distinct approximation of the frontier orbitals and consequently to a red-shift of both absorption and fluorescence. Finally, we demonstrated the applicability of some oligomers as dopants for OLEDs by electrogenerated chemiluminescence (ECL).

  为了克服高阶寡聚噻吩的不溶性并同时提高它们在分子掺杂有机发光二极管(OLEDs)应用中的可加工性,我们合成了苯基取代的、苯基稠合的和螺芴基桥连的寡聚噻吩1-5。研究发现这些化合物在极性溶剂中的溶解度显著提高了最多三个数量级,并对它们在溶液中的光学和电化学性质进行了研究。与未修饰的寡聚噻吩(6-8)相比,苯基取代和通过桥连中心联噻吩基团引入螺环核心仅略微影响了光学和氧化还原性质,这反映了构象的微小变化和取代基之间几乎完全的电子分离。相比之下,寡聚物链中异噻萘(苯并[c]噻吩)单元的存在导致前沿轨道的明显趋近,因此吸收和荧光都发生红移。最后,我们通过电化学发光(ECL)证明了某些寡聚物作为OLED掺杂剂的适用性。
• One-Pot Oxidation and Bromination of 3,4-Diaryl-2,5-dihydrothiophenes Using Br₂:  Synthesis and Application of 3,4-Diaryl-2,5-dibromothiophenes
  作者：Yizhe Dang、Yi Chen

  DOI：10.1021/jo071172i

  日期：2007.8.31

  (1b−5b) was synthesized by a one-pot reaction of 3,4-diaryl-2,5-dihydrothiophenes with Br2 reagent in excellent yield (83−92%). It was found that Br2 performed a double function (oxidation and bromination) during the conversion of 3,4-diaryl-2,5-dihydrothiophenes to 3,4-diaryl-2,5-dibromothiophenes. The application of 3,4-diaryl-2,5-dibromothiophenes used as building blocks was also investigated. Employing

  通过3,4-二芳基-2,5-二氢噻吩与Br 2试剂的一锅反应以优异的收率（83-92 ）合成了一类3,4-二芳基-2,5-二溴噻吩（1b - 5b）％）。发现Br 2在3，4-二芳基-2，5-二氢噻吩转化为3，4-二芳基-2，5-二溴噻吩的过程中​​具有双重功能（氧化和溴化）。还研究了3,4-二芳基-2,5-二溴噻吩作为建筑材料的应用。以3,4-二苯基-2,5-二溴噻吩（1b）为模板，通过Suzuki偶联反应制备了2,3,4,5-四芳基噻吩类。这为制备2,3,4,5-四芳基噻吩提供了一种新的简单方法。
• Synthesis, Structure, and Magnetic Properties of Bithiophene- and Terthiophene-Linked Manganese Metal–Organic Frameworks
  作者：Lyndsey D. Earl、Brian O. Patrick、Michael O. Wolf

  DOI：10.1021/ic401305c

  日期：2013.9.3

  A series of metal-organic frameworks (MOFs) containing manganese centers and oligothiophene dicarboxylate linkers have been synthesized: [Mn(3PhT(2)DC)(DMF)(0.4)s(F12.0)2..s5.1.5 5DMF] (1), [Mn6(3F1T2PC)6. (DMF)3(-120)5"xDMF"YH20] (2), [Mn(T3DC)(H20)2] (3), [Mn(T3DC)(H20)1.3] (4), and [Mn(Ph2T3DC)(DMF)2] (5) (H23PhT2DC = 3,3'-dipheny1-2,2-bithiophene-5,5'-dicarboxylic acid; H23HT2DC:= 3,3'-dihexy1-2,2'bithiophene-5,5'-dicarboxylic acid; H2T3DC = 2,2':5',2"".ter,thiophene-5,5 '-dicarboxylic acid; H2Ph2T3DC = 3',4'-dipheny1-2,2':5',2"-terthiophene-5,5"-dicarboxylic acid, DMF = N,N-dimethylformamide). Compound 1 exists as a 2D sheet, 2-4 are 3D frameworks, and 5 is a ID chain. Compounds 3 and 4 are " isomers, and 3-5 are the first examples of crystallographically characterized terthiophene coordination polymers. In the case of 1, 2, and 5, the extended structure is sensitive to beta substitution of the oligothiophene linkers. Compounds 1-3 and S show antiferromagnetic behavior with typical values of g and J, and 3 exhibits a spin canting transition at 40 K.