3,4-bis(hexyloxy)thiophene-2-carboxaldehyde | 230949-88-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,4-bis(hexyloxy)thiophene-2-carboxaldehyde
• 英文别名: 3,4-dihexyloxythiophene-2-carbaldehyde；3,4-dihexyloxythiophene-5 carbaldehyde；2-formyl-3,4-dihexyloxythiophene；3,4-Dihexoxythiophene-2-carbaldehyde
• CAS: 230949-88-9
• 化学式: C₁₇H₂₈O₃S
• 分子量: 312.474
• InChiKey: LGVVWADVOHVYER-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  21
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  63.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,4-bis(hexyloxy)thiophene-2-carboxaldehyde 在 sodium hydride 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以99%的产率得到3,4-bis(hexyloxy)thiophen-2-methanol
  参考文献：
  名称：

  支链吡咯啉生色团的合成及非线性光学性质

  摘要：

  制备了具有刚性-柔性树突的新型三氰基吡咯啉（TCP）生色团，用于二阶非线性光学（NLO）应用。使用紫外可见光谱，核磁共振光谱和质谱对发色团进行了充分表征。热重分析（TGA）表明，生色团具有出色的热稳定性。大λ最大和高铬合物的影响表明，发色团具有较大的二阶非线性光学。电光系数（[R 33）在掺杂的发色团的聚测定（双酚A碳酸酯）在1310nm，最高基波波长膜γ 33实现是217 PMV -1。版权所有©2010 John Wiley＆Sons，Ltd.

  DOI：

  10.1002/poc.1772
• 作为产物：
  描述：

  2,5-dicarboxy-3,4-dihexyloxythiophene 在 copper(I) oxide 、 三氯氧磷 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 2.0h， 生成 3,4-bis(hexyloxy)thiophene-2-carboxaldehyde
  参考文献：
  名称：

  Low Oxidation Potential Tetrathiafulvalene Analogues Based on 3,4-Dialkoxythiophene π-Conjugating Spacers

  摘要：

  Tetrathiafulvalene analogues involving dihexyloxythiophene (1), ethylenedioxythiophene (2), and bis(3,4-dihexyloxy-2-thienyl)ethylene (3) as conjugating spacer and diversely substituted at the 1,3-dithiole ring (R) have been synthesized. Electronic absorption spectra show the expected decrease of HOMO-LUMO gap when increasing the electron-releasing power of R or the length of the conjugating spacer. Cyclic voltammetry (CV) shows that whereas compounds 1 and 2 are reversibly oxidized into their cation radical and dication through two one-electron steps, for compounds 3 the dication is formed directly via a two-electron transfer. Comparison of the data for compounds 2 and 3 with those of their respective analogues based on thiophene and dithienylethylene shows that introduction of the electron-donating alkoxy groups at the 3 and 4 positions of the thiophene ring produces a 150-200 mV negative shift of the first redox potential (E degrees(1)). On the other hand, CV data for compounds 1 and 2 reveal several unusual features such as E degrees(1) approximate to 0.10 V/SCE ranking among-the lowest known to date and a Coulombic repulsion between positive charges in the dication larger than for the analogue ct-donors based on unsubstituted thiophene. These results are interpreted by a major reorganization of the electronic distribution in the donor molecule due to alkoxy groups: the highest electron density moving from the 1,3-dithiole moiety toward the central thiophene ring.

  DOI：

  10.1021/jo981312b

文献信息

• Design and Synthesis of Push−Pull Chromophores for Second-Order Nonlinear Optics Derived from Rigidified Thiophene-Based π-Conjugating Spacers
  作者：Jean-Manuel Raimundo、Philippe Blanchard、Nuria Gallego-Planas、Nicolas Mercier、Isabelle Ledoux-Rak、Rolland Hierle、Jean Roncali

  DOI：10.1021/jo010713f

  日期：2002.1.1

  Two series of push-pull chromophores built around thiophene-based pi-conjugating spacers rigidified either by covalent bonds or by noncovalent intramolecular interactions have been synthesized and characterized by UV-vis spectroscopy, electric field induced second harmonic generation (EFISH) and differential scanning calorimetry. Comparison of the linear and second-order nonlinear optical properties

  合成了两个系列的推挽生色团，它们围绕通过共价键或通过非共价分子内相互作用而硬化的基于噻吩的pi共轭间隔基构建，并通过紫外可见光谱，电场诱导的二次谐波产生（EFISH）和差示扫描量热法进行了表征。基于共价桥联二噻吩基乙烯（DTE）间隔基的发色团与基于开链DTE的类似物的生色团的线性和二阶非线性光学性质的比较表明，间隔基的刚性共同导致吸收最大值的显着红移分子二次超极化率（mu beta）大大提高，达到了迄今为​​止报道的最高值。NLO-phores的第二系列是从2,2' -双（3,4-乙撑二氧噻吩）（BEDOT）π共轭间隔基。如X射线和UV-vis数据所示，在这种情况下，间隔物的刚性源自硫和氧原子之间的非共价分子内相互作用。再次，与基于未取代的联噻吩间隔基的母体化合物的比较揭示了最大吸收的显着红移和μβ的大大增强。为了区分乙二氧基的电子和几何效应的贡献，已经合成了基于3，4-乙二氧基噻吩（ED
• The synthesis of new double-donor chromophores with excellent electro-optic activity by introducing modified bridges
  作者：Yuhui Yang、Haoran Wang、Fenggang Liu、Dan Yang、Shuhui Bo、Ling Qiu、Zhen Zhen、Xinhou Liu

  DOI：10.1039/c4cp05829a

  日期：——

  New double-donor chromophores were synthesized and large hyperpolarizability can be effectively translated into large electro-optic coefficients.

  新的双供体色团已经合成，大的超极化率可以有效地转化为大的电光系数。
• Systematic study on the optimization of a bis(<i>N</i>,<i>N</i>-diethyl)aniline based NLO chromophore <i>via</i> a stronger electron acceptor, extended π-conjugation and isolation groups
  作者：Shuhui Bo、Ya Li、Tongtong Liu、Fuyang Huo、Hongyan Xiao、Hua Zhang、Zhuo Chen

  DOI：10.1039/d1tc05684k

  日期：——

  A series of highly polarizable chromophores A–F based on the same bis(N,N-diethyl)aniline donor, the tricyanofuran (TCF) and CF3–Ph–TCF acceptor linked via thiophene, alkoxy chain modified thiophene and extended thiophene π-conjugations has been synthesized and systematically investigated. Density functional theory (DFT) calculations suggested that the optimal structure F showed a first-order hyperpolarizability

  一系列高度极化的发色团 A-F 基于相同的双 ( N , N-二乙基)苯胺供体、三氰呋喃 (TCF) 和 CF 3 -Ph-TCF 受体，通过噻吩、烷氧基链修饰的噻吩和扩展噻吩 π-共轭已被合成并系统地研究。密度泛函理论 (DFT) 计算表明，最优结构 F 的一阶超极化率 ( β ) 值为 551.0 × 10 -30esu 对于单个分子而言相对较高。这些发色团表现出良好的热稳定性，其分解温度均高于 220 °C。通过在无定形聚碳酸酯 (APC) 中以 25 wt% 的负载量掺杂发色团 A-F，在 1310 nm 处的电光系数 ( r 33 ) 可达 149、139、148、142、252 和 305 pm V -1分别达到。对于具有烷氧基链作为隔离基团、扩展噻吩桥和CF 3的F ，标准化的r 33值增加到每（V分子） 19.37 × 10 -19 pm cc–Ph–TCF 受体，表明隔离
• Enhancement of electro-optic properties of bis(N,N-diethyl)aniline based second order nonlinear chromophores by introducing a stronger electron acceptor and modifying the π-bridge
  作者：Hua Zhang、Yuhui Yang、Hongyan Xiao、Fenggang Liu、Fuyang Huo、Lu Chen、Zhuo Chen、Shuhui Bo、Ling Qiu、Zhen Zhen

  DOI：10.1039/c7tc01175j

  日期：——

  yz1 and yz2 based on the same bis(N,N-diethyl)aniline donor, the tricyanofuran acceptor (TCF) and CF3-Ph-TCF acceptor linked together via thiophene and the modified thiophene π-conjugation have been synthesized and systematically investigated in this paper. Density functional theory (DFT) calculations suggested that the molecular quadratic hyperpolarizability (β) value of CF3-Ph-TCF based chromophore

  基于相同的双（N，N-二乙基）苯胺供体，三氰呋喃受体（TCF）和CF3-Ph-TCF受体的一系列高度极化的生色团y1，y2，yz1和yz2，它们通过噻吩和修饰的噻吩π连接在一起-共轭已被合成和系统地进行了研究。密度泛函理论（DFT）计算表明，基于CF3-Ph-TCF的发色团的分子二次超极化率（β）值分别比基于TCF的发色团大16.8％和46.8％。这些生色团具有良好的热稳定性，其分解温度均高于230℃。此外，与使用TCF受体从发色团（y1和y2）获得的结果相比，这些带有CF3-Ph-TCF受体的新生色团（yz1和yz2）显示出更好的分子内电荷转移（ICT）吸收（108nm和97nm红移）。通过在无定形聚碳酸酯（APC）中掺杂25wt％的高载量的发色团y1，y2，yz1和yz2，在1310时V-1的电光（EO）系数（r33）高达149、139、142和252 pm可以分别实现nm。具有双（N
• Extended benzodifuran–thiophene systems connected with azomethine junctions: synthesis and electronic properties
  作者：Chady Moussallem、Frédéric Gohier、Pierre Frère

  DOI：10.1016/j.tetlet.2015.07.030

  日期：2015.9

  The synthesis of extended benzodifuran-thiophene systems connected by azomethine junctions is described. The electronic properties of these systems, studied by UV-vis spectroscopy and cyclic voltammetry, are discussed in relation with the electron withdrawing groups grafted on the benzodifuran unit and the electron donor ability of the thiophene moieties. (C) 2015 Elsevier Ltd. All rights reserved.