4,4-didodecyl-2,6-bis(trimethylstannyl)-4H-silolo[3,2-b:4,5-b']dithiophene | 1175641-12-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: 4,4-didodecyl-2,6-bis(trimethylstannyl)-4H-silolo[3,2-b:4,5-b']dithiophene
• 英文别名: 5,5’-Bis(trimethylstannyl)-3,3’-di-2-dodecilsilylene-2,2’-bithiophene；5,5'-bis(trimethylstannyl)-3,3'-di-n-dodecylsilylene-2,2'-bithiophene；(7,7-didodecyl-10-trimethylstannyl-3,11-dithia-7-silatricyclo[6.3.0.02,6]undeca-1(8),2(6),4,9-tetraen-4-yl)-trimethylstannane
• CAS: 1175641-12-9
• 化学式: C₃₈H₇₀S₂SiSn₂
• 分子量: 856.611
• InChiKey: SASHTGYUFNNHFS-UHFFFAOYSA-N

物化性质

• 沸点：
  704.1±70.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  12.29
• 重原子数：
  43
• 可旋转键数：
  24
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  56.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4,4-didodecyl-2,6-bis(trimethylstannyl)-4H-silolo[3,2-b:4,5-b']dithiophene 、 4-溴-2,1,3-苯并噻二唑 在 四(三苯基膦)钯 作用下， 以 甲苯 为溶剂， 反应 0.5h， 以85%的产率得到5,5'-bis(benzo[2,1,3]thiadiazole)-3,3'-di-n-dodecylsilylene-2,2'-bithiophene
  参考文献：
  名称：

  Band gap control in conjugated oligomers and polymers via Lewis acids

  摘要：

  一种改变具有带隙和包含π-离域电子的化合物的电子和光学性质的方法。该方法包括将Lewis酸络合到框架内的碱性位点，形成具有与化合物不同带隙的Lewis酸加合物。与化合物的λmax相比，Lewis酸加合物的λmax可以向更长波长移动。在各种版本中，化合物可以是共轭寡聚体、共轭聚合物或包含共轭π-电子系统的小分子。还提供包括Lewis酸加合物的电子器件。

  公开号：

  US20110028656A1
• 作为产物：
  描述：

  4,4-didodecyl-4H-silolo[3,2-b:4,5-b']dithiophene 、 三甲基氯化锡 在 正丁基锂 、 水 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以95.7%的产率得到4,4-didodecyl-2,6-bis(trimethylstannyl)-4H-silolo[3,2-b:4,5-b']dithiophene
  参考文献：
  名称：

  Band gap control in conjugated oligomers and polymers via Lewis acids

  摘要：

  一种改变具有带隙和包含π-离域电子的化合物的电子和光学性质的方法。该方法包括将Lewis酸络合到框架内的碱性位点，形成具有与化合物不同带隙的Lewis酸加合物。与化合物的λmax相比，Lewis酸加合物的λmax可以向更长波长移动。在各种版本中，化合物可以是共轭寡聚体、共轭聚合物或包含共轭π-电子系统的小分子。还提供包括Lewis酸加合物的电子器件。

  公开号：

  US20110028656A1

文献信息

• Organic small molecule semiconducting chromophores for use in organic electronic devices
  申请人：Welch Gregory C.

  公开号：US09893294B2

  公开（公告）日：2018-02-13

  Small organic molecule semi-conducting chromophores containing a pyridalthiadiazole, pyridaloxadiazole, or pyridaltriazole core structure are disclosed. Such compounds can be used in organic heterojunction devices, such as organic small molecule solar cells and transistors.

  本发明涉及含有吡啶硫二唑，吡啶氧二唑或吡啶三唑核心结构的小有机分子半导体色团。这些化合物可以用于有机异质结器件，例如有机小分子太阳能电池和晶体管。
• Pyridalthiadiazole-Based Narrow Band Gap Chromophores
  作者：Zachary B. Henson、Gregory C. Welch、Thomas van der Poll、Guillermo C. Bazan

  DOI：10.1021/ja209331y

  日期：2012.2.29

  levels both in solution and in the bulk. Substitution of different alkyl chains on D(2) gives rise to controllable melting and crystallization temperatures and tailored solubility. Alterations to the core donor D(2) lead to readily identifiable changes in all properties studied. Finally, the regiochemistry of the pyridal N-atom in the PT heterocycle was investigated. The tailoring of structures via subtle

  含有吡啶并 [2,1,3] 噻二唑 (PT) 单元的 π 共轭材料最近在溶液处理的分子本体异质结 (BHJ) 有机光伏器件中实现了 6.7% 的创纪录功率转换效率。认识到这类新分子系统的重要性，并为了建立更具体的路径来预测所需固态特性的改进，我们着手系统地改变分子框架并评估结构-性能关系。因此，提供了 13 种结构相关的 D(1)-PT-D(2)-PT-D(1) 化合物的合成和性质，其中 D 表示与 PT 相比相对富电子的芳香链段。使用吸收光谱、循环伏安法、热重分析、差示扫描量热法和溶解度分析。对封端 D(1) 单元的更改允许对溶液中和本体中的电子能级进行精细控制。D(2) 上不同烷基链的取代产生可控的熔化和结晶温度以及定制的溶解度。对核心供体 D(2) 的改变导致所有研究性质的容易识别的变化。最后，研究了 PT 杂环中吡啶 N 原子的区域化学。通过所呈现的分子系列中的细微结构修改来定制结
• Synthesis and structure study of copolymers from thiadiazole fused indolocarbazole and dithienosilole
  作者：Qiliang Chen、Lianjie Zhang、Shaker Ebrahim、Moataz Soliman、Cheng Zhang、Qiquan Qiao

  DOI：10.1016/j.polymer.2012.11.006

  日期：2013.1

  We report synthesis and characterization of two D-A polymers (PSDT-C12 and PSDT-EH) with different side chains. Both polymers are based on alternate 12,13-dioctyl-indolo[2,3-a][1,2,5]thiadiazolo[3,4-c] carbazole (TDZIC) and dithienosilole derivative units in polymer main chain. We used TDZIC to enlarge the 2D conjugated plane of acceptor monomers by fusing benzothiadiazole (BT) unit with an indole unit having alkyl groups. PSDT-C12 exhibited 10 nm redshift compared to PSDT-EH in solid films, while their absorption spectra were almost identical in solutions. Since the backbone and side chains on the indolocarbazole group are the same, the redshift on PSDT-C12 could be resulted from the dodecyl (C12) side chain on the dithienosilole unit and different molecular weight between these two polymers. PSDT-C12 has a larger molecular weight than PSDT-EH. Therefore possibly both side chains and molecular weight contributed to the difference in the absorption spectra in solid films. The straight C-12 side chain has less steric hindrance than the branched EH side chain in solid films. PSDT-C12 has a longer main chain (larger molecule weight) than PSDT-EH, which can favour a more extended main chain interaction. The vibronic peak at 519 nm and shoulder at 563 nm in the PSDT-C12 film further confirmed stronger main chain interaction. Geometry optimization showed that head-tail (HT)-PSDT had a more twisting conjugated backbone with larger dihedral angle between dithienosilole unit and thiadiazole-fused ring compared to head-head/tail-tail (HH/TT)-PSDT. (C) 2012 Elsevier Ltd. All rights reserved.
• Band gap control in conjugated oligomers and polymers via Lewis acids
  申请人：Bazan Guillermo C.

  公开号：US20110028656A1

  公开（公告）日：2011-02-03

  A method for altering the electronic and optical properties of a chemical compound having a band gap and a framework that includes π-delocalized electrons. The method includes complexing a Lewis acid to a basic site within the framework to form a Lewis acid adduct having a band gap that differs from the band gap of the chemical compound. The λ max of the Lewis acid adduct can be shifted to a longer wavelength in comparison to the λ max of the chemical compound. In various versions, the chemical compound can be a conjugated oligomer, a conjugated polymer, or a small molecule comprising a conjugated π-electron system. Electronic devices that include Lewis acid adducts are also provided.

  一种改变具有带隙和包含π-离域电子的化合物的电子和光学性质的方法。该方法包括将Lewis酸络合到框架内的碱性位点，形成具有与化合物不同带隙的Lewis酸加合物。与化合物的λmax相比，Lewis酸加合物的λmax可以向更长波长移动。在各种版本中，化合物可以是共轭寡聚体、共轭聚合物或包含共轭π-电子系统的小分子。还提供包括Lewis酸加合物的电子器件。