3,4-bis(hexyloxy)-2-thiophene | 211235-81-3

• 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)-2-thiophene
• 英文别名: 3,4-bis(hexyloxy)thiophene；3,4-dihexyloxythiophene；3,4-Dihexoxythiophene
• CAS: 211235-81-3
• 化学式: C₁₆H₂₈O₂S
• 分子量: 284.463
• InChiKey: OMANTHZRUHGCNC-UHFFFAOYSA-N

物化性质

• 沸点：
  361.7±22.0 °C(Predicted)
• 密度：
  0.974±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  19
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  46.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3,4-bis(hexyloxy)-2-thiophene 在 正丁基锂 、 四甲基乙二胺 、 三氯氧磷 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 2.5h， 生成 2,5-bis<4,5-bis(methylsulfanyl)-2H-1,3-dithiol-2-ylidenemethyl>-3,4-dihexyloxythiophene
  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
• 作为产物：
  描述：

  2,5-dicarbethoxy-3,4-dihexyloxythiophene 在 喹啉 、 铜 、 potassium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 5.0h， 生成 3,4-bis(hexyloxy)-2-thiophene
  参考文献：
  名称：

  取代基对导电的聚合物氧化还原电极的超电容性能的影响：聚（3'，4'-双（烷氧基）2,2'：5'，2”-三噻吩衍生物）

  摘要：

  这项工作报告了新型聚（3'，4'-双（烷氧基）对噻吩）衍生物（PTTOBu，PTTOHex和PTTOOct）的合成及其作为氧化还原活性电极的超级电容器应用。基于对噻吩的导电聚合物已被不同的烷基侧基（丁基，己基和辛基）衍生化，以研究烷基链长对表面形态和假电容性质的影响。电化学性能测试表明，烷基取代基的长度对聚合物电极的表面形态和电荷存储性能产生了显着影响。基于PTTOBu，PTTOHex和PTTOOct的电极在2.5 mA cm -2时的比电容达到94.3、227.3和443 F g -1在三电极配置中分别保持恒定的电流密度。此外，这些氧化还原活性电极在对称的10,000次充电/放电循环后，具有令人满意的13.5、29.3和60.7 W h kg -1的能量密度以及0.98、1和1.1 kW kg -1的功率密度，并具有良好的电容保持率固态微型超级电容器设备。©2017 Wiley Periodicals，Inc

  DOI：

  10.1002/pola.28927

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
• Synthesis and nonlinear optical properties of branched pyrroline chromophores
  作者：Jialei Liu、Wenjun Hou、Shuwen Feng、Ling Qiu、Xinhou Liu、Zhen Zhen

  DOI：10.1002/poc.1772

  日期：2011.6

  New tricyanopyrroline (TCP) chromophores with rigid–flexible dendron were prepared for second‐order nonlinear optical (NLO) application. The chromophores were fully characterized using ultraviolet‐visible spectroscopy, nuclear magnetic resonance spectroscopy and mass spectrometry. Thermal gravimetric analysis (TGA) revealed that the chromophores had excellent thermal stability. Large λmax and high

  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.
• Nucleophilic <i>ipso</i>-Substitution of Aryl Methyl Ethers through Aryl C–OMe Bond Cleavage; Access to Functionalized Bisthiophenes
  作者：Abhishek Kumar Mishra、Ajay Verma、Srijit Biswas

  DOI：10.1021/acs.joc.6b02701

  日期：2017.4.7

  A metal and solvent free strategy to functionalize aryl methyl ethers through direct nucleophilic substitution of aryl C–OMe bond has been described. A wide range of O, S, N, and C-centered uncharged nucleophiles has been successfully employed. Using this protocol, functional derivatives of bisthiophene have been synthesized in a straightforward way. The reactions are highly atom-efficient and generate

  已经描述了通过芳基C–OMe键的直接亲核取代来实现芳基甲基醚官能化的无金属和无溶剂策略。已经成功地采用了各种以O，S，N和C为中心的不带电亲核试剂。使用该协议，已经以简单的方式合成了双噻吩的功能性衍生物。该反应是高度原子效率的，并且产生甲醇作为唯一的副产物。
• Synthesis and Photovoltaic Properties of Polythiophene Incorporating with 3,4-Difluorothiophene Units
  作者：Linquan Huang、Dong Yang、Qiang Gao、Yan Liu、Shengmei Lu、Jian Zhang、Can Li

  DOI：10.1002/cjoc.201300505

  日期：2013.11

  Two polythiophene derivatives using fluorine atoms and hexyl or hexyloxy group as electron‐withdrawing and donating substituents have been synthesized. The introduction of fluorine atoms to the polythiophene backbones simultaneously lowers the HOMO and narrows the bandgap, and the stronger electron‐donating ability of hexyloxy side chain further reduces the bandgap. As a result, poly[3‐hexylthiophene‐2

  合成了两种使用氟原子和己基或己氧基作为吸电子和供电子取代基的聚噻吩衍生物。将氟原子引入聚噻吩主链同时降低了HOMO并缩小了带隙，更强的己氧基侧链供电子能力进一步降低了带隙。结果，聚[3-己基噻吩-2,5-二基-alt-3,4-二氟噻吩]（PHTDFT）的HOMO和带隙为−5.31 / 1.83 eV，聚[3,4-二己基噻吩-2-5,5- [diyl-alt-3,4-difluorothiophene]（PDHOTDFT）显示HOMO和带隙为−5.14 / 1.68 eV，均低于P3HT的−4.76 / 2.02 eV。受益于较低的HOMO，PHTDFT：PC 61BM（1：1）聚合物太阳能电池在太阳光AM1.5（100 mW / cm 2）下的功率转换效率为1.11％，施加的开路电压为0.79V 。
• 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。