5,5'-bis(4-bromo-5-fluoro-7-benzo[c][1,2,5]thiadiazole)-3,3'-di-2-ethylhexylsilylene-2,2’-bithiophene | 1589072-33-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻二唑类
• 英文名称: 5,5'-bis(4-bromo-5-fluoro-7-benzo[c][1,2,5]thiadiazole)-3,3'-di-2-ethylhexylsilylene-2,2’-bithiophene
• 英文别名: 5,5'-bis{4-(6-fluoro-7-bromo-[c][1,2,5]thiadiazolobenzene)}-3,3'-di-2-ethylhexylsilylene-2,2'-bithiophene；7,7'-(4,4-bis(2-ethylhexyl)-4H-silolo[3,2-b:4,5-b']dithiophene-2,6-diyl)bis(4-bromo-5-fluorobenzo[c][1,2,5]thiadiazole)
• CAS: 1589072-33-2
• 化学式: C₃₆H₃₈Br₂F₂N₄S₄Si
• 分子量: 880.879
• InChiKey: KJOOKWYCMFJDMH-UHFFFAOYSA-N

物化性质

• 沸点：
  803.7±65.0 °C(Predicted)
• 密度：
  1.53±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  12.93
• 重原子数：
  49.0
• 可旋转键数：
  14.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  51.56
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  4-(4,4-bis(2-ethylhexyl)-6-(trimethylstannyl)-4H-silolo[3,2-b:4,5-b']dithiophen-2-yl)-7-(5'-hexyl-[2,2'-bithiophen]-5-yl)-[1,2,5]thiadiazolo[3,4-c]pyridine 、 5,5'-bis(4-bromo-5-fluoro-7-benzo[c][1,2,5]thiadiazole)-3,3'-di-2-ethylhexylsilylene-2,2’-bithiophene 在 四(三苯基膦)钯 作用下， 以 甲苯 为溶剂， 反应 0.82h， 以70%的产率得到C₁₂₂H₁₄₆F₂N₁₀S₁₄Si₃
  参考文献：
  名称：

  Design and Properties of Intermediate-Sized Narrow Band-Gap Conjugated Molecules Relevant to Solution-Processed Organic Solar Cells

  摘要：

  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.

  DOI：

  10.1021/ja413144u
• 作为产物：
  描述：

  44’-双(2-乙基己酯)-55’-双(三甲基锡)-噻吩[32-b:23-d]硅杂环戊二烯 、 5-氟-4,7-二溴-[2,1,3]苯并噻二唑 在 四(三苯基膦)钯 作用下， 以 甲苯 、 甲醇 、 正己烷 为溶剂， 以26%的产率得到5,5'-bis(4-bromo-5-fluoro-7-benzo[c][1,2,5]thiadiazole)-3,3'-di-2-ethylhexylsilylene-2,2’-bithiophene
  参考文献：
  名称：

  具有对称的F原子远侧/远侧取向的基于规则二硫杂硅基和双硫杂诺基的小分子

  摘要：

  该研究描述了一系列区域规整二噻吩并的的合成和表征（3,2-B; 2'，3'- d）-silole（DTSI） -和二噻吩并（3,2-B; 2'，3'- d）-germole（DTGe）基小分子-7,7'-（4,4-双（2-乙基己基）-4 H -silolo [3,2- b：4,5- b ']二噻吩-2， 6-二基）双（5-氟-4-（5'-己基-[2,2'-联噻吩] -5-基）苯并[ c ] [1,2,5]噻二唑）（DTSi（BTFTh 2）2），7,7'-（4,4-双（2-乙基己基）-4 H-锗[[3,2- b：4,5 - b ']二噻吩-2,6-二基）双（5-氟-4-（5'-己基-[2,2'-联噻吩] -5-基）苯并[ c ] [1,2,5]噻二唑）（DTGe（BTFTh 2）2），7,7'-（4,4-双（2-乙基己基）-4 H -silolo [3,2- b：4,5 - b ']二噻吩-2

  DOI：

  10.1016/j.dyepig.2018.03.010

文献信息

• Topological Considerations for the Design of Molecular Donors with Multiple Absorbing Units
  作者：Lai Fan Lai、John A. Love、Alexander Sharenko、Jessica E. Coughlin、Vinay Gupta、Sergei Tretiak、Thuc-Quyen Nguyen、Wai-Yeung Wong、Guillermo C. Bazan

  DOI：10.1021/ja501711m

  日期：2014.4.16

  The molecule AT1, with two weakly conjugated chromophores, was designed, synthesized, and examined within the context of its film forming tendencies. While the addition of the second chromophore to the central core enables broadening of the absorption spectrum, this change is mostly apparent in films that are grown slowly. Grazing incidence X-ray scattering (GI-WAXS) analysis indicates that these spectral characteristics correspond to an increase in solid state ordering. This information, in combination with differential scanning calorimetry, suggests that the overall molecular shape provides a kinetic barrier to crystallization. As a result, one finds the absence of molecular order when AT1 is combined with PC71BM in solution-cast blends. These findings highlight the importance of molecular topology when designing molecular components for solar cell devices.