3,4-dioctyloxythiophene | 207802-19-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,4-dioctyloxythiophene
• 英文别名: 3,4-dioctoxythiophene
• CAS: 207802-19-5
• 化学式: C₂₀H₃₆O₂S
• 分子量: 340.571
• InChiKey: OTUYNPNPIIFVGN-UHFFFAOYSA-N

物化性质

• 熔点：
  29.5-30.5 °C
• 沸点：
  420.1±25.0 °C(Predicted)
• 密度：
  0.951±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.4
• 重原子数：
  23
• 可旋转键数：
  16
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 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-dioctyloxythiophene 在 sodium acetate 、 三氯氧磷 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 28.5h， 生成 3,4-dioctyloxythiophene-2-carbaldehyde-N,N-diphenylhydrazone
  参考文献：
  名称：

  Synthesis of new N, N-diphenylhydrazone dyes for solar cells: Effects of thiophene-derived π-conjugated bridge

  摘要：

  Four novel D-pi-A hydrazone dyes (HT, HM, HE, and HO) with an N, N-diphenylhydrazone moiety as the electron donor, different thiophene-derived pi-conjugated bridges and a cyanoacrylic acid moiety as the electron acceptor have been designed and synthesized for the application in dye-sensitized solar cells. The influences of thiophene-derived bridges on the photoelectrochemical and photovoltaic performance of these hydrazone dyes were investigated. Results demonstrate that the introduction of 3,4-dialkyloxythiophene could red-shift the dye's absorption spectrum due to the enhancement of the electron-donating ability of pi-conjugated bridges. Importantly, electrochemical impedance spectroscopy analysis reveal that 3,4-dialkyloxythiophene bridge could change the charge recombination resistance at the TiO2/dye/electrolyte interface and as a result to improve the open-circuit photovoltage. Among the four dyes, HO exhibits the maximum power conversion efficiency of 5.83% (V-oc = 0.65 V, J(sc) = 12.69 mA/cm(2), FF = 0.707) under simulated AM 1.5 irradiation (100 mW/cm(2)). (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2011.08.014
• 作为产物：
  描述：

  2,5-噻吩二羧酸,3,4-二甲氧基- 在 喹啉 、 copper chromite 、 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 32.0h， 生成 3,4-dioctyloxythiophene
  参考文献：
  名称：

  Synthesis and crystal structures of 2,3,12,13-tetraalkoxy-21,23-dithiaporphyrins and 2,3-dialkoxy-21-monothiaporphyrins

  摘要：

  The tetraalkoxy and dialkoxy substituted 21,23-dithiaporphyrins and 21-monothiaporphyrins, respectively, having methoxy, butoxy, octyloxy and dodecyloxy substituents at beta-thiophene carbons were synthesized and characterized. The X-ray structure was solved for tetrabutoxy substituted 21,23-dithiaporphyrin and it exhibited a more planar structure compared with unsubstituted S2TPP, whereas the dimethoxy substituted 21-monothiaporphyrin showed a saddle shaped structure similar to unsubstituted STPPH. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.09.008

文献信息

• Yellow electrochromic polymer materials with fine tuning electrofluorescences by adjusting steric hindrance of side chains
  作者：Jian Liu、Yuchen Shi、Jingchuan Wu、Mei Li、Jianming Zheng、Chunye Xu

  DOI：10.1039/c7ra03097e

  日期：——

  conjugated yellow-to-transmissive electrochromic (EC) polymers were designed and synthesized to research their structure–property relationships, achieving electrofluorescent (EF) switching with applied external potential. These bifunctional materials are based on repeat units of bi-phenyl-1,3,4-oxadiazole and thiophene derivatives with different side chains. The polymers present a similar yellow color

  设计并合成了一系列新型的导电共轭黄色至透射电致变色（EC）聚合物，以研究它们的结构与性质之间的关系，并在施加外部电势的情况下实现了电致荧光（EF）转换。这些双功能材料基于具有不同侧链的联苯-1,3,4-恶二唑和噻吩衍生物的重复单元。聚合物呈现相似的黄色，并在施加还原电势的情况下发出各种荧光，并且它们可以变成几乎透明且具有氧化电势的非荧光。还详细表征了光学对比度，电化学，电致变色和电荧光转换特性。还制造了一种包含这些聚合物的设备，该设备可以同时实现电致变色和电致荧光转换，
• Synthesis and crystal structure of 2,3,12,13-tetraalkoxy-21, 23-dithiaporphyrinsElectronic supplementary information (ESI) available: 1H-NMR, LD-MS spectra and X-ray crystal structure data. See http://www.rsc.org/suppdata/cc/b2/b208017f/
  作者：Neeraj Agarwal、Sarada P. Mishra、Anil Kumar、C.-H. Hung、M. Ravikanth

  DOI：10.1039/b208017f

  日期：2002.11.4

  21,23-Dithiaporphyrins with methoxy, butoxy, octyloxy and dodecyloxy substituents at β-thiophene carbons were synthesised for the first time and the crystal structure of the butoxy derivative indicated that the substituents at the β-thiophene carbons induce more planarity in the porphyrin ring.

  首次合成了在β-噻吩碳上带有甲氧基、丁氧基、辛氧基和十二氧基取代基的21,23-二硫吡咯并。丁氧基衍生物的晶体结构表明，β-噻吩碳上的取代基使得吡咯环更加平面化。
• Alternating copolymers of diketopyrrolopyrrole or benzothiadiazole and alkoxy-substituted oligothiophenes: spectroscopic, electrochemical and spectroelectrochemical investigations
  作者：M. Gora、W. Krzywiec、J. Mieczkowski、E.C. Rodrigues Maia、G. Louarn、M. Zagorska、A. Pron

  DOI：10.1016/j.electacta.2014.07.147

  日期：2014.10

  donor-acceptor (DA) copolymers consisting of either diketopyrrolopyrrole or benzothiadiazole A units and alkoxy- or alkyl-substituted oligothiophene D units were synthesized. For all prepared copolymers the measured XPS spectra (C1s, S2p, N1s and O1s) were in a very good agreement with the expected chemical constitution. Spectroscopic studies of the synthesized copolymers showed that their optical band gaps were

  合成了由二酮吡咯并吡咯或苯并噻二唑A单元和烷氧基或烷基取代的低聚噻吩D单元组成的一系列可溶液处理的半导体供体-受体（DA）共聚物。对于所有制备的共聚物，测得的XPS光谱（C1，S2p，N1和O1）与预期的化学组成非常吻合。合成共聚物的光谱研究表明，其光学带隙受烷氧基取代基的存在支配，在含二酮吡咯并吡咯A单元的聚合物中，其电子给予特性导致其间隙进一步缩小，从而产生带隙低于1.3 eV的半导体。在电化学带隙中观察到了相同的趋势，但是发现其值为约。比相应的光学带隙值高0.4 eV。计算了两种合成共聚物的振动模型，目的是明确地归因于观察到的拉曼模式，并支持对电化学氧化引起的光谱变化的解释。已经确定，具有苯并噻二唑A单元的共聚物的电化学氧化掺杂仅限于其中形成的聚阳离子的电荷局部存在的低聚噻吩链段。相反，在具有二酮吡咯并吡咯A段的聚合物的情况下，施加在低聚噻吩链段上的电荷向二酮吡咯并吡咯单元脱离。这些
• Substituent effect on supercapacitive performances of conducting polymer-based redox electrodes: Poly(3′,4′-bis(alkyloxy) 2,2′:5′,2″-terthiophene) derivatives
  作者：Deniz Yiğit、Melis Aykan、Mustafa Güllü

  DOI：10.1002/pola.28927

  日期：2018.3.1

  over the surface morphologies and charge storage properties of polymer electrodes. PTTOBu, PTTOHex, and PTTOOct‐based electrodes have reached up to specific capacitances of 94.3, 227.3, and 443 F g−1 at 2.5 mA cm−2 constant current density, respectively, in a three‐electrode configuration. Besides, these redox‐active electrodes have delivered satisfactory energy densities of 13.5, 29.3, and 60.7 W h kg−1

  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
• Elektrisch leitende Beschichtungsmasse, Verfahren zu ihrer Herstellung und ihre Verwendung
  申请人：HOECHST AKTIENGESELLSCHAFT

  公开号：EP0328981A2

  公开（公告）日：1989-08-23

  Eine Beschichtungsmasse, bestehend aus einem löslichen elektrisch leitenden Polymer von substituierten Thiophenen und gegebenenfalls einem löslichen nichtleitenden Polymer ergibt, aus der Lösung in einem aprotischen Lösemittel aufgebracht, gut haftende elektrisch leitende Schichten auf nicht leitenden oder halbleitenden Materialien. Auf diese Weise lassen sich antistatisch ausgerüstete Folien und Fasern und Formkörper für Zwecke der Elektronik und Elektrik herstellen.

  由取代噻吩的可溶性导电聚合物和可溶性非导电聚合物组成的涂层组合物，在非导电或半导电材料上从溶液中涂抹，可产生附着力良好的导电层。通过这种方法，可以生产出抗静电薄膜、纤维以及用于电子和电气用途的模制产品。