5,5'-bis{4-(7-bromo-[1,2,5]thiadiazolo[3,4-c]pyridine)}-3,3'-di-2-ethylhexylsilylene-2,2’-bithiophene | 1351374-93-0

• 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: 5,5'-bis{4-(7-bromo-[1,2,5]thiadiazolo[3,4-c]pyridine)}-3,3'-di-2-ethylhexylsilylene-2,2’-bithiophene
• 英文别名: 5,5’-bis{(4-(7-bromo-1,2,5-thiadiazolo[3,4-c]pyridinyl))}-3,3’-di-2-ethylhexylsilyl-2,2’-bithiophene；7-Bromo-4-[10-(7-bromo-[1,2,5]thiadiazolo[3,4-c]pyridin-4-yl)-7,7-bis(2-ethylhexyl)-3,11-dithia-7-silatricyclo[6.3.0.02,6]undeca-1(8),2(6),4,9-tetraen-4-yl]-[1,2,5]thiadiazolo[3,4-c]pyridine；7-bromo-4-[10-(7-bromo-[1,2,5]thiadiazolo[3,4-c]pyridin-4-yl)-7,7-bis(2-ethylhexyl)-3,11-dithia-7-silatricyclo[6.3.0.02,6]undeca-1(8),2(6),4,9-tetraen-4-yl]-[1,2,5]thiadiazolo[3,4-c]pyridine
• CAS: 1351374-93-0
• 化学式: C₃₄H₃₈Br₂N₆S₄Si
• 分子量: 846.873
• InChiKey: IPQYJLYZWPMENN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.44
• 重原子数：
  47
• 可旋转键数：
  14
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  190
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2-(2-乙基己基)噻吩 、 5,5'-bis{4-(7-bromo-[1,2,5]thiadiazolo[3,4-c]pyridine)}-3,3'-di-2-ethylhexylsilylene-2,2’-bithiophene 在 正丁基锂 、 四(三苯基膦)钯 、 三丁基氯化锡 作用下， 以 四氢呋喃 、 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 73.0h， 以620 mg的产率得到4-[7,7-Bis(2-ethylhexyl)-10-[7-[5-(2-ethylhexyl)thiophen-2-yl]-[1,2,5]thiadiazolo[3,4-c]pyridin-4-yl]-3,11-dithia-7-silatricyclo[6.3.0.02,6]undeca-1(8),2(6),4,9-tetraen-4-yl]-7-[5-(2-ethylhexyl)thiophen-2-yl]-[1,2,5]thiadiazolo[3,4-c]pyridine
  参考文献：
  名称：

  [EN] LIQUID CRYSTALLINE MEDIUM
  [FR] MILIEU CRISTALLIN LIQUIDE

  摘要：

  本发明涉及一种液晶介质，其包括由苯并噻二唑和相关的扩展杂环衍生物制成的二色性染料，该介质用于光学、电光和电子目的，特别是在调节辐射能量从外部空间进入内部空间的设备中，例如在窗户中。该发明还涉及包含根据本发明的液晶介质的装置。一些新的二色性染料被揭示。

  公开号：

  WO2019243216A1
• 作为产物：
  描述：

  2,6-二溴-4,4-双(2-乙基己基)-4H-硅杂环戊二烯并[3,2-b:4,5-b’]二噻吩 在 四(三苯基膦)钯 、 正丁基锂 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 48.5h， 生成 5,5'-bis{4-(7-bromo-[1,2,5]thiadiazolo[3,4-c]pyridine)}-3,3'-di-2-ethylhexylsilylene-2,2’-bithiophene
  参考文献：
  名称：

  FLUORINATED DYE COMPOUNDS FOR ORGANIC SOLAR CELLS

  摘要：

  包含第一电极、第二电极和位于第一电极和第二电极之间并与其电连接的有源层的电子或光电子器件。该有源层包括至少一种染料化合物，其中包括小分子有机太阳能电池。

  公开号：

  US20180114930A1

文献信息

• Impact of Regiochemistry and Isoelectronic Bridgehead Substitution on the Molecular Shape and Bulk Organization of Narrow Bandgap Chromophores
  作者：Gregory C. Welch、Ronald C. Bakus、Simon J. Teat、Guillermo C. Bazan

  DOI：10.1021/ja310694t

  日期：2013.2.13

  A comparison of two classes of small molecules relevant to the field of organic electronics is carried out at the molecular and supramolecular levels. First, two molecules that differ only in the position of a pyridyl N-atom within an acceptor fragment are compared and contrasted. X-ray investigation of single crystals reveals that positioning the pyridyl N-atoms proximal to the molecules center changes

  在分子和超分子水平上进行了与有机电子领域相关的两类小分子的比较。首先，比较和对比两个仅在受体片段中吡啶基 N 原子位置不同的分子。单晶的 X 射线研究表明，将吡啶基 N 原子置于分子中心附近会通过将分子弯曲成香蕉形状来改变分子形状。其次，我们证明了分子的香蕉形状可以通过用 C 或 Ge 原子替换二噻吩噻吩片段中的 Si 原子来控制。在这里，使用环戊二噻吩或二噻吩并锗作为内部富电子单元分别导致共轭骨架弯曲的减少或增加。
• Design and Properties of Intermediate-Sized Narrow Band-Gap Conjugated Molecules Relevant to Solution-Processed Organic Solar Cells
  作者：Xiaofeng Liu、Yanming Sun、Ben B. Y. Hsu、Andreas Lorbach、Li Qi、Alan J. Heeger、Guillermo C. Bazan

  DOI：10.1021/ja413144u

  日期：2014.4.16

  Increases in the molecular length of narrow band gap conjugated chromophores reveal potentially beneficial optical and electronic properties, thermal stabilities, and high power conversion efficiencies when integrated into optoelectronic devices, such as bulk heterojunction organic solar cells. With the objective of providing useful information for understanding the transition from small-sized molecules to polymers, as well as providing a general chemical design platform for extracting relationships between molecular structure and bulk properties, we set out to vary the electron affinity of the molecular backbone. Therefore, a series of donor (D) acceptor (A) alternating narrow band gap conjugated chromophores were synthesized based on the general molecular frameworks: D-1-A(1)-D-2-A(2)-D-2-A(1)-D-1 and D-1-A(1)-D-2-A(2)-D-2-A(2)-D-2-A(1)-D-1. When the central electron-accepting moiety (A(2)) was varied or modified, two classes of molecules could be compared. First, we showed that the alteration of one single electron-accepting group, while maintaining the shape of the molecular framework, can effectively impact the optical properties and energy levels of the molecules. DFT ground state structure optimizations show similar "U" shape conformations among these molecules. Second, we examined how the site-specific introduction of fluorine atom(s) modifies the thermal properties in the solid state, while maintaining relatively similar optical and electrochemical features of interest. Structure property relationship of such molecular systems could be rationally evaluated in the aspects of thermal-responsive molecular organizations in the solid state and dipole moments both in the ground and excited states. The impact of molecular structure on charge carrier mobilities in field effect transistors and the performance of photovoltaic devices were also studied.
• FLUORINATED DYE COMPOUNDS FOR ORGANIC SOLAR CELLS
  申请人：Next Energy Technologies, Inc.

  公开号：US20180114930A1

  公开（公告）日：2018-04-26

  Electronic or optoelectronic device comprising a first electrode, a second electro, and an active layer arranged between and in electrical connection with the first and the second electrode. The active layer comprises at least one dye compound, which comprises small-molecule organic solar cells.

  包含第一电极、第二电极和位于第一电极和第二电极之间并与其电连接的有源层的电子或光电子器件。该有源层包括至少一种染料化合物，其中包括小分子有机太阳能电池。
• [EN] LIQUID CRYSTALLINE MEDIUM<br/>[FR] MILIEU CRISTALLIN LIQUIDE
  申请人：MERCK PATENT GMBH

  公开号：WO2019243216A1

  公开（公告）日：2019-12-26

  The present invention relates to a liquid crystalline medium comprising dichroitic dyes made of benzothiadiazoles and related extended heterocyclic derivatives, the use of said medium for optical, electro-optical and electronic purposes, in particular in devices for regulating the passage of radiation energy from an outside space into an inside space, for example in windows. The invention further relates to devices containing the liquid crystalline medium according to the invention. Some new dichroitic dyes are disclosed.

  本发明涉及一种液晶介质，其包括由苯并噻二唑和相关的扩展杂环衍生物制成的二色性染料，该介质用于光学、电光和电子目的，特别是在调节辐射能量从外部空间进入内部空间的设备中，例如在窗户中。该发明还涉及包含根据本发明的液晶介质的装置。一些新的二色性染料被揭示。