2,2':5',2"-terthiophene-5,5"-dicarboxylic acid | 87145-86-6

• 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: 2,2':5',2"-terthiophene-5,5"-dicarboxylic acid
• 英文别名: 2,2':5',2''-terthiophene-5,5''-dicarboxylic acid；5-[5-(5-Carboxythiophen-2-yl)thiophen-2-yl]thiophene-2-carboxylic acid
• CAS: 87145-86-6
• 化学式: C₁₄H₈O₄S₃
• 分子量: 336.413
• InChiKey: QFHRPBFDQUKMCX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  159
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2,2':5',2"-terthiophene-5,5"-dicarboxylic acid 在 镍 作用下， 以 水 为溶剂， 反应 20.0h， 以85%的产率得到十四烷二酸
  参考文献：
  名称：

  2,2':5',2"-Terthiophene-5-carboxylic acid and 2,2':5',2"-terthiophene-5,5"-dicarboxylic acid

  摘要：

  DOI：

  10.1021/jo00170a040
• 作为产物：
  描述：

  alpha-三联噻吩 以90%的产率得到
  参考文献：
  名称：

  KAGAN, J.;ARORA, S. K.;UESTUENOL, A., J. ORG. CHEM., 1983, 48, N 22, 4076-4078

  摘要：

  DOI：

文献信息

• On-resin dimerization incorporates a diverse array of π-conjugated functionality within aqueous self-assembling peptide backbones
  作者：Geeta S. Vadehra、Brian D. Wall、Stephen R. Diegelmann、John D. Tovar

  DOI：10.1039/c0cc00301h

  日期：——

  We report a convenient method to incorporate π-electron units into peptides that assemble into amyloid-like supramolecular polymers, discussing the scope of the process and preliminary characterization of the resulting nanomaterials. Self-assembly manipulates these “electronic peptides” into delocalized sub-10 nm 1-D nanostructures under completely aqueous conditions.

  我们报告了一种便捷的方法，将Ï-电子单元加入肽中，使其组装成类似淀粉样的超分子聚合物，并讨论了这一过程的范围以及由此产生的纳米材料的初步特性。在完全无水的条件下，自组装技术可将这些 "电子肽 "操纵成局部10纳米以下的一维纳米结构。
• SELF-ASSEMBLING PEPTIDES BEARING ORGANIC ELECTRONIC FUNCTIONALITY AND APPLICATIONS EMPLOYING THE SAME
  申请人：Tovar John Dayton

  公开号：US20120101022A1

  公开（公告）日：2012-04-26

  The aqueous self-assembly of oligopeptide-flanked π-conjugated molecules into discrete one-dimensional nanostructures is described. Unique to these molecules is the fact that the π-conjugated unit has been directly embedded within the peptide backbone by way of a synthetic amino acid with π-functionality that is compatible with standard Fmoc-based peptide synthesis or by way of a diacid or other bis(electrophile) that can covalently cross-link peptide chains presented on a synthesis support. The peptide-based molecular designs enforce intimate π-π communication within the aggregates after charge-screening and self-assembly, making these nanostructures attractive for optical or electronic applications in biological environments. In other embodiments, a convenient method to incorporate π-electron units into peptides that assemble into amyloid-like supramolecular polymers is disclosed. Self-assembly manipulates these “electronic peptides” into delocalized sub-10 nm one dimensional (1-D) nanostructures under completely aqueous conditions.

  本文介绍了寡肽-π共轭分子在水相中自组装成离散一维纳米结构的过程。这些分子的独特之处在于，π共轭单元直接嵌入到寡肽骨架中，通过合成具有π功能的氨基酸，该氨基酸与标准的Fmoc基肽合成兼容，或通过二酸或其他双(亲电子)与合成支撑上呈现的肽链共价交联。寡肽分子的设计在电荷屏蔽和自组装后强制实现聚集体内部的亲-亲作用，使这些纳米结构在生物环境中具有光学或电子应用的吸引力。在其他实施例中，本文还揭示了一种将π电子单元方便地纳入到聚集成类淀粉样超分子聚合物的寡肽中的方法。自组装将这些“电子寡肽”操纵成分散的亚10纳米一维(1-D)纳米结构，在完全水相条件下实现。
• Photophysical Properties of <i>cis</i>-Mo₂ Quadruply Bonded Complexes and Observation of Photoinduced Electron Transfer to Titanium Dioxide
  作者：Samantha E. Brown-Xu、Malcolm H. Chisholm、Christopher B. Durr、Terry L. Gustafson、Thomas F. Spilker

  DOI：10.1021/ja504944d

  日期：2014.8.13

  thienyl-2-carboxylate (Th), 2,2'-bithienyl-5-carboxylate (BTh), and 2,2':5',5″-terthienyl-5-carboxylate (TTh). The compounds have been characterized by proton nuclear magnetic resonance ((1)H NMR), ultraviolet-visible (UV-vis) absorption and emission, differential pulse voltammetry, and time-resolved transient absorption and infrared (IR) spectroscopy. An X-ray crystal structure was obtained for the thienyl

  已经制备了化合物顺式-Mo2(DAniF)2(L)2，其中 DAniF = (N,N')-p-二甲脒基和 L = 噻吩基-2-羧酸酯 (Th), 2,2'-二噻吩基- 5-羧酸盐 (BTh) 和 2,2':5',5"-terthienyl-5-carboxylate (TTh)。这些化合物已通过质子核磁共振 ((1) H NMR)、紫外-可见 (UV-vis) 吸收和发射、差分脉冲伏安法以及时间分辨瞬态吸收和红外 (IR) 光谱进行表征。获得了噻吩基配合物的 X 射线晶体结构。相关的盐 [(n)Bu4N]2[Mo2(DAniF)2(TTh-CO2)2]，其中 TTh- = 2,2':5',2"-terthienyl-5,5"-dicarboxylate，具有还制备并用于将复合物附着到 TiO2 纳米颗粒上。后者已通过基态傅里叶变换红外光谱 (FTIR) 和飞秒时间分辨红外光谱进行表征。时间分辨数据为从
• 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.
• Porous Metal−Organic Truncated Octahedron Constructed from Paddle-Wheel Squares and Terthiophene Links
  作者：Zheng Ni、Abderrahim Yassar、Tarek Antoun、Omar M. Yaghi

  DOI：10.1021/ja052055c

  日期：2005.9.1

  A metal-organic truncated octahedron (termed MOP-28) has been constructed from six rigid square-shaped Cu2(CO2)4 paddle-wheel building units and twelve 2,2':5',2' '-terthiophene-5,5' '-dicarboxylate (TTDC) linkers. TTDC linker in the cis,cis conformation provides the critical 90 degrees linkage for this unique construction. The porous structure of MOP-28 is maintained even after the removal of guest species, as evidenced by this compound's nitrogen sorption isotherm of Type I characteristics and unprecedented surface area (Langmuir surface area 1100 m2/g, BET surface area 914 m2/g) among materials composed of discrete molecules.