5''-hexyl-[2,2':5',2''-terthiophene]-5-carbaldehyde | 745820-38-6

• 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: 5''-hexyl-[2,2':5',2''-terthiophene]-5-carbaldehyde
• 英文别名: 5-[5-(5-Hexylthiophen-2-yl)thiophen-2-yl]thiophene-2-carbaldehyde
• CAS: 745820-38-6
• 化学式: C₁₉H₂₀OS₃
• 分子量: 360.565
• InChiKey: FJPQTQPLEYAOMG-UHFFFAOYSA-N

物化性质

• 熔点：
  116 °C
• 沸点：
  486.5±45.0 °C(Predicted)
• 密度：
  1.206±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 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：

  5''-hexyl-[2,2':5',2''-terthiophene]-5-carbaldehyde 、 4-(12-bromododecyloxy)phenylacetonitrile 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以43%的产率得到
  参考文献：
  名称：

  Nanostructured Liquid Crystals Combining Ionic and Electronic Functions

  摘要：

  New molecular materials combining ionic and electronic functions have been prepared by using liquid crystals consisting of terthiophene-based mesogens and terminal imidazolium groups. These liquid crystals show thermotropic smectic A phases. Nanosegregation of the pi-conjugated mesogens and the ionic imidazolium moieties leads to the formation of layered liquid-crystalline (LC) structures consisting of 2D alternating pathways for electronic charges and ionic species. These nanostructured materials act as efficient electrochromic redox systems that exhibit coupled electrochemical reduction and oxidation in the ordered bulk states. For example, compound 1 having the terthienylphenylcyanoethylene mesogen and the imidazolium triflate moiety forms the smectic LC nanostructure. Distinct reversible electrochromic responses are observed for compound 1 without additional electrolyte solution on the application of double-potential steps between 0 and 2.5 V in the smectic A phase at 160 degrees C. In contrast, compound 2 having a tetrafluorophenylterthiophene moiety and compound 3 having a phenylterthiophene moiety exhibit irreversible cathodic reduction and reversible anodic oxidation in the smectic A phases. The use of poly(3,4-ethylenedioxythiophene)-poly(4-styrene sulfonate) (PEDOT-PSS) as an electron-accepting layer on the cathode leads to the distinct electrochromic responses for 2 and 3. These results show that new self-organized molecular redox systems can be built by nanosegregated pi-conjugated liquid crystals containing imidazolium moieties with and without electroactive thin layers on the electrodes.

  DOI：

  10.1021/ja101366x
• 作为产物：
  描述：

  2-(tri-n-butyl)stannyl-5,2'-bithiophene 在 N-溴代丁二酰亚胺(NBS) 、 正丁基锂 、 tetrakis(triphenylarsine)palladium(0) 、 溶剂黄146 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 3.25h， 生成 5''-hexyl-[2,2':5',2''-terthiophene]-5-carbaldehyde
  参考文献：
  名称：

  Poly(α-vinyl-ω-alkyloligothiophene) Side-Chain Polymers. Synthesis, Fluorescence, and Morphology

  摘要：

  The synthesis of polyvinyl polymers by radical polymerization of alpha-vinyl-omega-alkyl-terminated thiophene and bi-, ter-, and quaterthiophenes is reported. The photoluminescence properties of the polymers in solution and in thin film are described. In thin film, self-assembly-induced white photoluminescence was observed for poly(5-vinyl-5"'-hexylquaterthiophene). For this polymer, single crystals with rectangular shape and micrometer size were obtained by drop casting from CS2. MM3 calculations on model diads and triads indicate that, on increasing the size of the side groups, van der Waals interactions promote the stacking of the pendants on the same side of the polyvinyl chain.

  DOI：

  10.1021/ma049102q

文献信息

• Effect of Side-Chain Architecture on the Optical and Crystalline Properties of Two-Dimensional Polythiophenes
  作者：Cheng-Yu Kuo、Yu-Chen Huang、Chuen-Yo Hsiow、Yu-Wen Yang、Ching-I Huang、Syang-Peng Rwei、Hsing-Lin Wang、Leeyih Wang

  DOI：10.1021/ma4007945

  日期：2013.8.13

  different conformations conjugated to the polythiophene main chain via vinyl linkage provided the ability to control the molecular organization, hence affecting the optoelectronic and electrochemical properties of 2D polymers. TD-DFT calculation with the B3LYP/6-31+g(d) function on electronic structures of the monomers was consistent with the experimental results. It suggested that the energetic states

  本研究报告了合成具有共轭三噻吩-亚乙烯基侧链的三种新型二维（2D）聚噻吩衍生物-poly 3-（5“ -hexyl-2,2'：5'，2” -terthiophenyl-5-乙烯基）噻吩-alt-噻吩}（P1），聚3-（5,5“-二己基-2,2'：5'，2”-三噻吩基-3'-乙烯基）噻吩-alt-噻吩}（P2）和聚3-（4,4“-二己基-2,2：5'，2”-三噻吩-3'-乙烯基）噻吩-alt-噻吩}（P3）-通过静寂偶联反应合成的。通过乙烯基键与聚噻吩主链共轭的具有不同构象的对噻吩侧链提供了控制分子组织的能力，因此影响了2D聚合物的光电和电化学性能。用B3LYP / 6-31 + g（d）函数对单体的电子结构进行TD-DFT计算与实验结果一致。这表明HOMO和LUMO的能量状态高度依赖于侧链架构。通过旋铸法制备的这些聚噻吩薄膜显示出从300到700 nm的较宽吸收范围，该范围比纯聚（3
• Symmetrical and unsymmetrical donor–acceptor–donor organic dyes: Design, synthesis and characterization. Engineering panchromic absorbance
  作者：Akhil Gupta、Abdelselam Ali、Ante Bilic、Th Birendra Singh、Richard A. Evans

  DOI：10.1016/j.dyepig.2014.04.008

  日期：2014.9

  central acceptor were made. The central acceptors were dicyanovinylidene and 1,3-diethylthiobarbituric acid derivatives of 2-indanone in the set of symmetrical dyes and dicyanovinylidene in unsymmetrical dyes. The different acceptors allowed the tuning of optoelectronic properties. All the new materials were soluble in variety of organic solvents, such as chloroform, toluene and chlorobenzene. With

  已经设计，合成和表征了一系列基于施主-受主-施主（D–A–D）图案的四种新型有机半导体材料，以了解对称/不对称和受体强度的影响。在这种策略中，两种对称染料在中心受体的两端带有2-（1,3,3-三甲基吲哚-2-亚乙基）乙醛衍生的供体，而两种基于2-（1,3,3-三甲基吲哚-在中心受体的一端制备了2-亚丙基）乙醛衍生的供体，在另一端制备了一个低聚噻吩的供体。中心接受体是对称染料组中的2-茚满酮的二氰基亚乙烯基和1，3-二乙基硫代巴比妥酸衍生物，而在不对称染料中是二氰基亚乙烯基。不同的受体允许调节光电特性。所有新材料都可溶于多种有机溶剂，例如氯仿，甲苯和氯苯。随着受体强度的增加，最长波长吸收最大值的波长以及各自的消光系数增加，这导致带隙减小。对称分子给出相对窄的强初级吸收率，而非对称分子给出较弱但跨越整个可见光区域的双峰或非常宽的吸收峰，以提供全色吸收。
• New alternating copolymers of fluorene and triphenylamine bearing terthiophene and acceptor groups in the side chains: Synthesis and photovoltaic properties
  作者：Shuang Li、Zhicai He、Aoshu Zhong、Jian Yu、Hongbin Wu、Yue Zhou、Su’an Chen、Cheng Zhong、Jingui Qin、Zhen Li

  DOI：10.1016/j.polymer.2011.09.022

  日期：2011.10

  A series of conjugated copolymers (P1 and P2-CN–P4-CN) were prepared, in which two kinds of side chains were designed: one was the repeating units similar to that of P3HT, with the aim to increase the compatible with PC61BM and the hole mobility; another one was the acceptor groups connected with the electron-rich backbone through the conjugated 3,4-ethylenedioxythiophene bridge, in order to broaden

  制备了一系列共轭共聚物（P1和P2-CN–P4-CN），其中设计了两种侧链：一种是类似于P3HT的重复单元，目的是增加与PC 61的相容性BM和空穴迁移率；另一个是通过共轭的3,4-亚乙基二氧噻吩桥与富电子主链连接的受体基团，以扩大吸收并降低LUMO含量。通过控制这两种侧链的比例，可以对所得共轭聚合物的吸收带进行微调，而它们的能级几乎保持不变。结果，相应设备的性能首先提高，然后下降，这表明这两个侧链的不同功能之间将达到平衡。
• One-dimensional porphyrin H-aggregates induced by solvent polarity
  作者：Myung-Seok Choi

  DOI：10.1016/j.tetlet.2008.09.140

  日期：2008.12

  A series of new porphyrin derivatives possessing the side arms of alkyl-substituted thiophene oligomer were synthesized. The effects of solvent polarity on the formation of supramolecular assembly have been studied by UV-vis absorption, fluorescence emission, and TEM measurement. The linear-shape porphyrin derivatives bearing two thiophene pentamers at meso-position showed the significant spectral changes in both blue-shift and band broadening of Soret bands which indicate the formation of a relatively larger porphyrin H-aggregate that occurred in nonpolar solvent such as n-hexane. (c) 2008 Elsevier Ltd. All rights reserved.