4-formylphenyl thiophene-3-carboxylate | 1396273-08-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: 4-formylphenyl thiophene-3-carboxylate
• 英文别名: (4-Formylphenyl) thiophene-3-carboxylate；(4-formylphenyl) thiophene-3-carboxylate
• CAS: 1396273-08-7
• 化学式: C₁₂H₈O₃S
• 分子量: 232.26
• InChiKey: FVCBRFZGERGQGT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  71.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-formylphenyl thiophene-3-carboxylate 、 4-aminophenyl 4-dodecyloxybenzoate 以 乙醇 为溶剂， 反应 0.17h， 以72.8%的产率得到(E)-4-((4-(4-(dodecyloxy)benzoyloxy)phenylimino)methyl)phenyl thiophene-3-carboxylate
  参考文献：
  名称：

  Synthesis, Structural and Mesophase Characterization of Three Ring Based Thiophene Liquid Crystals

  摘要：

  Thiophene based calamitic mesogens are receiving paramount importance due to their applications in functional organic materials. The insertion of thiophene in the core unit favours a large change in mesophase characteristics as well as application properties in contrast to those mesogens with phenyl ring core alone. In this work, we report the structural as well as mesophase characterization of six mesogens which are built with a core of three phenyl rings and thiophene ring. The thiophene ring is placed at one end of the core and varied the other end with alkyl/alkoxy chains to investigate the mesophase characteristics. The molecular structures of representative mesogens are confirmed by means of FT-IR and Two-dimensional solution NMR techniques. An enantiotropic nematic phase is observed in all the cases as supported by HOPM and DSC techniques. The mesophase characteristics such as melting and clearing temperatures and phase stability are discussed. A dramatic increase in nematic phase stability for the synthesised mesogens is noticed in contrast to two phenyl ring based thiophene mesogens reported in literature.

  DOI：

  10.1080/15421406.2013.858013
• 作为产物：
  描述：

  3-噻吩甲酸 在 氯化亚砜 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 丁酮 为溶剂， 反应 5.5h， 生成 4-formylphenyl thiophene-3-carboxylate
  参考文献：
  名称：

  Synthesis, Structural and Mesophase Characterization of Three Ring Based Thiophene Liquid Crystals

  摘要：

  Thiophene based calamitic mesogens are receiving paramount importance due to their applications in functional organic materials. The insertion of thiophene in the core unit favours a large change in mesophase characteristics as well as application properties in contrast to those mesogens with phenyl ring core alone. In this work, we report the structural as well as mesophase characterization of six mesogens which are built with a core of three phenyl rings and thiophene ring. The thiophene ring is placed at one end of the core and varied the other end with alkyl/alkoxy chains to investigate the mesophase characteristics. The molecular structures of representative mesogens are confirmed by means of FT-IR and Two-dimensional solution NMR techniques. An enantiotropic nematic phase is observed in all the cases as supported by HOPM and DSC techniques. The mesophase characteristics such as melting and clearing temperatures and phase stability are discussed. A dramatic increase in nematic phase stability for the synthesised mesogens is noticed in contrast to two phenyl ring based thiophene mesogens reported in literature.

  DOI：

  10.1080/15421406.2013.858013

文献信息

• Molecular Order and Mesophase Investigation of Thiophene-Based Forked Mesogens
  作者：K. Rajasekhar Reddy、Nitin P. Lobo、T. Narasimhaswamy

  DOI：10.1021/acs.jpcb.6b05827

  日期：2016.7.14

  the two series reveal orientational order parameters of all rings of the core as well as terminal chains in the liquid crystalline phase. For both homologues, because of the asymmetry of ring I, the order parameter value is higher in contrast to ring II, ring III, and the thiophene ring. The chemical shifts and 13C–1H dipolar couplings of OCH2 carbons of the terminal dodecyloxy chains provide contrasting

  合成了由三个苯基环核和末端二烷氧基链构成的基于噻吩的棒状分子，该分子被识别为叉状介晶，并研究了它们的中间相性质和分子顺序。合成的叉状液晶元将作为四catenar或双叉状液晶元的模型化合物。基于噻吩与其余核的位置，实现了2-取代和3-取代的液晶元，其中末端烷氧基链的长度是变化的。使用热台偏振显微镜和差示扫描量热法评估中间相性能。对于这两个同系物，取决于末端烷氧基链的长度，注意到向列相单独出现或与近晶C相结合出现。使用可变温度粉末X射线衍射，对于代表性的液晶元，证实了近晶C相的层有序特征的存在。高分辨率固态两个系列的C 12同系物的13 C NMR测量揭示了液晶相中核的所有环以及末端链的取向顺序参数。对于两个同源物，由于环I的不对称性，与环II，环III和噻吩环相比，阶参数值更高。末端十二烷氧基链的OCH 2碳的化学位移和13 C– 1 H偶极偶合提供了相反的构象，反映了取向限制。此外，研究还
• A molecular insight on the supramolecular assembly of thiophene polymers
  作者：Chandrasekaran Suryanarayanan、Ezhakudiyan Ravindran、Soundaram Jeevarathinam Ananthakrishnan、Narayanasastri Somanathan、Asit Baran Mandal

  DOI：10.1039/c2jm30550j

  日期：——

  Herein, the relationship between supramolecularly self-assembled microstructures and the chemical structures of photoluminescent molecules is discussed. A series of non-amphiphilic molecules with different length alkyl chains (4–14), central mesogenic groups, and chemical linkers were designed and synthesized. Intricate analysis shows that the supramolecular assembly varies with change in torsion angle of the thiophene linking group on elongation of the alkyl chain. Small angle X-ray scattering measurement shows long range molecular interaction for lower alkyl chain length, AFM reveals circular domains for octyl and decyl alkyl group polymers. UV-Visible and photoluminescence studies in solution and thin-film show that the J-aggregate patterns for the circular domain of the polymer backbone has a major effect on the polymer absorbance, and produces a larger shift for the photoluminescence signals at higher wavelengths. Excitation polarisation studies show a change in molecular ordering in various colour regions with change in aggregation by means of maximum dichroic ratio for the circular domain assembly. Charge carrier mobility and cyclic voltammetry studies show higher mobility and reduced band gap for these circular domain polymers. Dynamic light scattering studies of octyl alkyl chain polymers show a bimodal distribution, which shows the apparent nature of anisotropy in solution.

  本文讨论了超分子自组装微结构与光致发光分子化学结构之间的关系。研究人员设计并合成了一系列具有不同长度烷基链（4-14）、中心介原基团和化学连接体的非两亲分子。复杂的分析表明，烷基链伸长时，噻吩连接基团的扭转角发生变化，超分子组装也随之变化。小角 X 射线散射测量显示，烷基链长度较低时，分子间的相互作用范围较长；原子力显微镜显示，辛基和癸基烷基聚合物具有圆形结构域。溶液和薄膜中的紫外可见光和光致发光研究表明，聚合物骨架环形结构域的 J-聚合模式对聚合物的吸光度有重大影响，并在较高波长下产生较大的光致发光信号偏移。激发偏振研究表明，随着环形结构域组装的最大二色性比率发生变化，不同颜色区域的分子有序性也发生了变化。电荷载流子迁移率和循环伏安法研究表明，这些环状结构域聚合物的迁移率更高，带隙更小。辛基烷基链聚合物的动态光散射研究显示出一种双峰分布，这表明了溶液中各向异性的明显性质。