4,4-didodecyl-4H-silolo[3,2-b:4,5-b']dithiophene | 1175641-09-4

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: 4,4-didodecyl-4H-silolo[3,2-b:4,5-b']dithiophene
• 英文别名: 3,3'-di-n-dodecylsilylene-2,2'-bithiophene；3,3atrade mark-Di-n-dodecylsilylene-2,2'-bithiophene；7,7-didodecyl-3,11-dithia-7-silatricyclo[6.3.0.02,6]undeca-1(8),2(6),4,9-tetraene
• CAS: 1175641-09-4
• 化学式: C₃₂H₅₄S₂Si
• 分子量: 530.998
• InChiKey: DOLDBQUDQYWOTB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.19
• 重原子数：
  35
• 可旋转键数：
  22
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.75
• 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-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
• 作为产物：
  描述：

  3,3'-二溴-2,2'-联噻吩 、 二(十二烷基)二氯硅烷 在 正丁基锂 、 水 、 氯化铵 作用下， 以 四氢呋喃 为溶剂， 以61.5%的产率得到4,4-didodecyl-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

• Band Gap Control in Conjugated Oligomers via Lewis Acids
  作者：Gregory C. Welch、Robert Coffin、Jeff Peet、Guillermo C. Bazan

  DOI：10.1021/ja902789w

  日期：2009.8.12

  A simple and effective strategy for optical band gap control is demonstrated through the use of a novel small acceptor/donor/acceptor molecule, 1, and group-13 Lewis acids. Chromophore 1 contains a dithienolesilole donor unit end-capped with benzo-2,1,3-thiadiazole (BT) acceptor units. Addition to 1 of stoichiometeric quantities of Lewis acids of varying strength resulted in the formation of Lewis adducts with progressively red-shifted primary charge-transfer absorption bands. These complexes have absorption spectra that approach those of known conjugated copolymers containing related units. NMR spectroscopy and X-ray diffraction studies revealed that 1 binds 2 equiv of Lewis acid via the nitrogen at the 3-position of BT.
• 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。