5-hexadecylbenzo[1,2-b:3,4-b':5,6-d'']trithiophene | 1283076-42-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: 5-hexadecylbenzo[1,2-b:3,4-b':5,6-d'']trithiophene
• 英文别名: 9-Hexadecyl-3,8,15-trithiatetracyclo[10.3.0.02,6.07,11]pentadeca-1,4,6,9,11,13-hexaene
• CAS: 1283076-42-5
• 化学式: C₂₈H₃₈S₃
• 分子量: 470.808
• InChiKey: XFCYHUVEURXMKB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.2
• 重原子数：
  31
• 可旋转键数：
  15
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  84.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-hexadecylbenzo[1,2-b:3,4-b':5,6-d'']trithiophene 在 四(三苯基膦)钯 、 Aliquat 336 、 叔丁基锂 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 生成 4,14-Bis(5-bromo-3-hexylthiophen-2-yl)-9-hexadecyl-3,8,15-trithiatetracyclo[10.3.0.02,6.07,11]pentadeca-1,4,6,9,11,13-hexaene
  参考文献：
  名称：

  Benzotrithiophene Copolymers: Influence of Molecular Packing and Energy Levels on Charge Carrier Mobility

  摘要：

  The planar benzotrithiophene unit (BTT) was incorporated into four different donor polymers, and by systematically changing the nature and positioning of the solubilizing alkyl side chains along the conjugated backbone, the polymers' frontier energy levels and optoelectronic properties were controlled. Reducing the steric hindrance along the polymer backbone lead to strong interchain aggregation and highly ordered thin films, achieving hole mobilities of 0.04 cm2/(V s) in organic thin film transistors. In an attempt to increase the polymer's processability and reduce chain aggregation, steric hindrance between alkyl side chains was exploited. As a result of the increased solubility, the film forming properties of the polymer could be improved, but at the cost of reduced hole mobilities in OFET devices, due to the lack of long-range order in the polymer films.

  DOI：

  10.1021/ma500163u
• 作为产物：
  描述：

  5-hexadecanoyl-2,3-bis(3-thienyl)thiophene 在 三氟化硼乙醚 、 一水合肼 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 potassium hydroxide 作用下， 以 二氯甲烷 、 二乙二醇 为溶剂， 生成 5-hexadecylbenzo[1,2-b:3,4-b':5,6-d'']trithiophene
  参考文献：
  名称：

  Benzotrithiophene - A Planar, Electron-Rich Building Block for Organic Semiconductors

  摘要：

  Several functionalized benzo[1,2-b:3,4-b':5,6-d']trithiophenes have been synthesized and characterized. The fully planar and highly electron-rich material shows great promise as the donor constituent in donor-acceptor type copolymers for use in organic electronics. As a proof of concept, a copolymer with the electron acceptor, 2,1,3-benzothiadiazole, has been prepared. Side-chain modifications have been employed to adjust both the electron-rich character of the monomer and the solubility and processability of the polymer.

  DOI：

  10.1021/ol200643z

文献信息

• [EN] TRIARYL- AND TRIHETEROARYL- BENZENE MONOMERS AND POLYMERS<br/>[FR] MONOMÈRES ET POLYMÈRES DE TRIARYL- ET TRIHÉTÉROARYL- BENZÈNES
  申请人：IMP INNOVATIONS LTD

  公开号：WO2012131084A1

  公开（公告）日：2012-10-04

  The invention relates to novel mono-, oligo- and polymeric compounds comprising substituted triaryl- and triheteroaryl benzene groups and their copolymers. The invention further relates to the methods of their synthesis, to organic semiconducting materials and blends, formulations and layers comprising them, and to electronic devices, like organic field effect transistors (OFETs) and organic photovoltaics (OPVs), comprising them.

  本发明涉及含有取代的三芳基和三杂芳基苯基基团及其共聚物的新型单体，寡聚体和聚合物。本发明还涉及它们的合成方法，有机半导体材料和混合物，配方和层，以及包含它们的电子设备，例如有机场效应晶体管（OFET）和有机光伏（OPV）。
• Benzotrithiophene polymers with tuneable bandgap for photovoltaic applications
  作者：Linyin Bian、Jingsheng Miao、Jiefeng Hai、Enwei Zhu、Jiangsheng Yu、Guidong Ge、Hongbin Wu、Weihua Tang

  DOI：10.1039/c4ra07644c

  日期：——

  Four benzotrithiophene (BTT) based donor–acceptor polymers have been prepared by alternating with diketopyrrolopyrrole (DPP), thiazolo[5,4-d]thiazole (TTz), thieno[3,4-c]pyrrole-4,6-dione (TPD) and thiadiazolo[3,4-g]quinoxaline (DTBTQx). The BTT-based polymers possess good solubility in common organic solvents and excellent thermal stability. PBTTDPP and PBTTDTBTQx possessed an optical bandgap of 1.27 eV and 1.20 eV, with absorption spectra extending to the near-infrared region. The bulk-heterojunction solar cells delivered a highest PCE of 1.39%, with a short circuit current of 5.46 mA cm−2, an open-circuit voltage of 0.51 V and a fill factor of 0.50.

  四种基于苯并三噻吩（BTT）的供体-受体聚合物已经通过二酮吡咯吡咯（DPP）、噻唑并[5,4-d]噻唑（TTz）、噻吩并[3,4-c]吡咯-4,6-二酮（TPD）和噻二唑并[3,4-g]喹喔啉（DTBTQx）的交替制备而成。基于BTT的聚合物在常见的有机溶剂中具有良好的溶解性和优异的热稳定性。PBTTDPP和PBTTDTBTQx的光带隙分别为1.27 eV和1.20 eV，吸收光谱延伸到近红外区域。体异质结太阳能电池的最高PCE为1.39%，短路电流为5.46 mA cm-2，开路电压为0.51 V，填充因子为0.50。