3'-formyl-2,2':5',2''-terthiophene | 393109-70-1

• 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'-formyl-2,2':5',2''-terthiophene
• 英文别名: 2,5-Dithiophen-2-ylthiophene-3-carbaldehyde
• CAS: 393109-70-1
• 化学式: C₁₃H₈OS₃
• 分子量: 276.404
• InChiKey: VSVQYMKNPCFIQR-UHFFFAOYSA-N

物化性质

• 熔点：
  68 °C
• 沸点：
  429.4±45.0 °C(Predicted)
• 密度：
  1.381±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  102
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3'-formyl-2,2':5',2''-terthiophene 在 哌啶 、 N-溴代丁二酰亚胺(NBS) 作用下， 以 氯仿 、 乙腈 为溶剂， 反应 1.0h， 生成 2-cyano-3-(5,5''-dibromo-[2,2';5',2'']terthiophen-3'-yl)acrylic acid methyl ester
  参考文献：
  名称：

  侧链带有吸电子基团的聚噻吩及其在体异质结太阳能电池中的应用

  摘要：

  可溶性聚噻吩轴承强吸电子基团，二氰基乙烯基[  CHC（CN）2 ]（PTDCN）和氰基甲氧羰乙烯基[  CHC（CO 2Me] CN]（PTCNME），已在侧链中制备。根据开始吸收计算出的PTDCN和PTCNME的光学带隙分别为1.70 eV和1.73 eV。使用表面分析仪（AC-2）测得的PTDCN和PTCNME的最高占据分子轨道能级分别为-5.53 eV和-5.29 eV，远低于聚（3-己基噻吩）（-4.81 eV）。为了研究光伏性能，制造了基于PTDCN和PTCNME的块状异质结聚合物太阳能电池，其结构为ITO / PEDOT：PSS /活性层/ LiF / Al，其中活性层是聚合物和[6,6]的混合膜。 -苯基C 61丁酸己酯（PC 61 BH）。根据电流密度-电压（J – V）估算太阳能电池参数）在100 mW / cm 2的AM1.5照明下的特性。基于PTCNME：PC

  DOI：

  10.1002/pola.24444
• 作为产物：
  描述：

  3-噻吩甲醛 在 四(三苯基膦)钯 氢溴酸 、 溴 、 sodium carbonate 作用下， 以 乙二醇二甲醚 为溶剂， 反应 16.0h， 生成 3'-formyl-2,2':5',2''-terthiophene
  参考文献：
  名称：

  Toward Functionalized Conducting Polymers:  Synthesis and Characterization of Novel β-(Styryl)terthiophenes

  摘要：

  Metal-catalyzed coupling methodologies have been employed in the synthesis of the key building block 3'-formyl-2,2':5',2"-terthiophene. Wittig olefinations with this aldehyde have produced five novel beta-styryl-substituted terthiophene monomers. These materials have been fully characterized by NMR spectroscopy, microanalysis, mass spectrometry, and X-ray crystal structure analysis. The results from the UV/visible spectroscopy and cyclic voltammetric investigations are reported.

  DOI：

  10.1021/jo034855g

文献信息

• Indanedione-Substituted Poly(terthiophene)s: Processable Conducting Polymers with Intramolecular Charge Transfer Interactions
  作者：Klaudia Wagner、Loretta L. Crowe、Pawel Wagner、Sanjeev Gambhir、Ashton C. Partridge、John C. Earles、Tracey M. Clarke、Keith C. Gordon、David L. Officer

  DOI：10.1021/ma902782x

  日期：2010.4.27

  The electrochemical and chemical syntheses of poly(terthiophene)s bearing an indanedione pendant group and displaying intramolecular charge transfer interactions have been achieved. The nature of the charge transfer interaction is characterized through DFT calculations and experimental studies, including resonance Raman spectroscopy and absorption and emission data through a Lippert−Mataga analysis

  已经实现了带有茚二酮侧基的聚（对噻吩）的电化学和化学合成，并显示出分子内的电荷转移相互作用。电荷转移相互作用的性质通过DFT计算和实验研究来表征，包括共振拉曼光谱以及通过Lippert-Mataga分析得到的吸收和发射数据。发现在带有茚满二酮的单体种类中存在的低能量跃迁具有相当大的电荷转移特性，偶极变化为11D。在化学聚合后的肼还原过程中发生了茚满二酮基团的分解。然而，在使用较温和的还原剂三乙醇胺之后，获得了可溶的，低分子量的茚二酮取代的聚合物（重均值为4500 Da）。据我们所知，这是使用三乙醇胺还原氧化聚噻吩的第一个实例，为肼提供了一种更温和，更安全的替代品。为了制备具有分子内电荷转移相互作用的较高分子量的可加工聚合物，合成了茚二酮取代的对噻吩和二己基对噻吩的共聚物。所产生的聚合物的电子共轭通过拉曼频率色散实验来表征，并显示出与其他取代的聚噻吩所观察到的相似的分散速率参数。为了制备具有
• Synthesis and characterization of novel conducting homopolymers based on amino β-styryl terthiophene
  作者：Hakim Mehenni、Lê H Dao

  DOI：10.1139/v08-136

  日期：2008.11.1

  Novel ECPs (electronic conducting polymers) based on amino β-styryl-substituted terthiophene (AST) were synthetized by direct electropolymerization. The ECPs were characterized by cyclic voltammetry, square-wave voltammetry, Fourier transform infrared (FTIR) spectroscopy, and X-ray photoelectron spectroscopy (XPS). The poly(amino β-styryl terthiophene) displayed cyclic and square-wave voltammograms with redox peaks that can be assigned to the aminophenyl moiety and the polyterthiophene backbone. The presence of free primary amine groups on the ECP film permitted further biological functionalization (i.e., covalent bonding of various bioreceptors on its surface). The electrochemical performance of Biotin grafted at the AST modified glassy carbon electrode was investigated to detect the Avidin protein in solution by cyclic voltammetry and square-wave voltammetry.Key words: electronic conducting polymer, electrode surface modification, biosensor, β-styryl-substitued terthiophene, functionalization, cyclic, square-wave voltammetry.

  通过直接电聚合法合成了基于氨基 β-苯乙烯基取代噻吩（AST）的新型 ECP（电子导电聚合物）。通过循环伏安法、方波伏安法、傅立叶变换红外光谱法和 X 射线光电子能谱法对 ECP 进行了表征。聚（氨基 β-苯乙烯基噻吩）显示出循环伏安图和方波伏安图，其氧化还原峰可归属于氨基苯基和聚噻吩骨架。ECP 薄膜上存在的游离伯胺基团允许进一步的生物功能化（即在其表面共价键合各种生物受体）。通过循环伏安法和方波伏安法研究了接枝在 AST 改性玻璃碳电极上的生物素的电化学性能，以检测溶液中的 Avidin 蛋白。
• The design and synthesis of porphyrin/oligiothiophene hybrid monomers
  作者：Gavin E. Collis、Wayne M. Campbell、David L. Officer、Anthony K. Burrell

  DOI：10.1039/b502517f

  日期：——

  In an effort to build effective photovoltaic cells based on porphyrin-functionalised polythiophenes we have focused on synthetic routes to three monomer types. By controlling the geometric structure of the monomer, oxidation of these materials should produce polymers with different architectural structures, and as a result, different opto-electronic properties. Employing Wittig protocols allowed access to monomers in which the porphyrin moiety is connected to the β-position of the thiophene via an alkene linkage. In addition, monomers were constructed using porphyrin condensation methods to afford α-thiophene meso-substituted porphryins. Another set of monomers was also prepared via porphyrin condensation routes, but instead utilising β-formylthiophenes. By utilising different formyloligothiophenes we were able to generate a series of monomers that can be used to control the loading of the porphyrin in the polythiophene matrix.

  为了构建基于卟啉官能化聚噻吩的高效光伏电池，我们集中研究了三种单体类型的合成路线。通过控制单体的几何结构，这些材料的氧化应该能够产生具有不同建筑结构的聚合物，从而导致不同的光电特性。采用Wittig反应策略使我们能够获得卟啉部分通过烯烃连接到噻吩β位的单体。此外，还使用卟啉缩合方法构建了α-噻吩间位取代卟啉的单体。另一组单体也是通过卟啉缩合路线制备的，但使用了β-甲酰基噻吩。通过利用不同的甲酰基低聚噻吩，我们能够生成一系列单体，以用于控制卟啉在聚噻吩矩阵中的负载。
• [EN] CONDUCTING POLYMERS WITH PORPHYRIN CROSS-LINKERS<br/>[FR] POLYMERES CONDUCTEURS COMPRENANT DES AGENTS DE RETICULATION PORPHYRINE
  申请人：UNIV WOLLONGONG

  公开号：WO2004067533A1

  公开（公告）日：2004-08-12

  The invention relates to a cross-linking monomer having the structure Q-(L)n-P-(L')m;-Q', where Q and Q' are polymerisable units, L and L' are linkers providing direct or indirect electronic communication between Q and P and between P and Q', and P is an electrofunctional unit, and also to polymers prepared from such monomers. Q for example may be a heteroaromatic ring such as thiophene, furan and pyrrole. The electrofunctional group may be, for example, porphyrin, substituted porphyrin, phthalocyanine or substituted phthalocyanine. The invention also relates to an electrofunctional material including a base material and a cross-linked polymer such as described.

  该发明涉及一种具有结构Q-(L)n-P-(L')m;-Q'的交联单体，其中Q和Q'是聚合单元，L和L'是提供Q与P之间以及P与Q'之间直接或间接电子通信的连接物，P是电功能单元，还涉及由这种单体制备的聚合物。例如，Q可以是噻吩、呋喃和吡咯等杂环环。电功能团可以是卟啉、取代卟啉、酞菁或取代酞菁等。该发明还涉及包括基材料和交联聚合物的电功能材料。
• Facile synthesis of acetylene-substituted terthiophenes
  作者：Pawel Wagner、Ashton C. Partridge、Kenneth W. Jolley、David L. Officer

  DOI：10.1016/j.tetlet.2007.07.032

  日期：2007.9

  A modified Horner–Emmons condensation reaction has been employed for the synthesis of acetylene-substituted terthiophenes in excellent yields. Conjugating 3′-aryl substituents to terthiophene using an ethyne rather than an ethene linker results in enhanced planarity of the resulting molecule as established by X-ray structural analysis of (2,2′:5′,2″-terthiophen-3′-yl)-4‴-pyridylethyne.

  改良的霍纳-埃蒙斯缩合反应已用于乙炔取代的对噻吩的高产率合成。通过乙炔而不是乙烯连接基将3'-芳基取代基与对噻吩缀合可提高所得分子的平面度，这是通过（2,2'：5'，2''-terthiophen-3'-的X射线结构分析确定的yl）-4‴-吡啶乙炔。