5,5'-bis[4-(7-bromobenzo[2,1,3]thiadiazole)]-3,3'-bis(2-ethylhexyl)silylene-2,2'-bithiophene | 1401032-28-7

• 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-(7-bromobenzo[2,1,3]thiadiazole)]-3,3'-bis(2-ethylhexyl)silylene-2,2'-bithiophene
• 英文别名: 5,5’-bis{4-(7-bromo-[1,2,5]thiadiazolobenzene)}-3,3’-di-2-ethylhexylsilylene-2,2’-bithiophene；4-Bromo-7-[10-(4-bromo-2,1,3-benzothiadiazol-7-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]-2,1,3-benzothiadiazole；4-bromo-7-[10-(4-bromo-2,1,3-benzothiadiazol-7-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]-2,1,3-benzothiadiazole
• CAS: 1401032-28-7
• 化学式: C₃₆H₄₀Br₂N₄S₄Si
• 分子量: 844.898
• InChiKey: RFHWZLGFDBCVIH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.65
• 重原子数：
  47
• 可旋转键数：
  14
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  165
• 氢给体数：
  0
• 氢受体数：
  8

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-(7-bromobenzo[2,1,3]thiadiazole)]-3,3'-bis(2-ethylhexyl)silylene-2,2'-bithiophene 在 四(三苯基膦)钯 作用下， 以 甲苯 为溶剂， 反应 0.82h， 以72%的产率得到C₁₂₂H₁₄₈N₁₀S₁₄Si₃
  参考文献：
  名称：

  Narrow-Band-Gap Conjugated Chromophores with Extended Molecular Lengths

  摘要：

  The influence of extending the molecular length of donor acceptor chromophores on properties relevant to organic optoelectronic devices has been studied by using two new narrow-band-gap systems. Most significantly, we find that the higher molecular weight systems exhibit higher thermal stabilities (beyond 200 degrees C) when introduced into field effect transistor devices. It is also possible to fabricate bulk heterojunction solar cells using PC61BM with power conversion efficiencies >6%. These high values are not heavily influenced by the blend composition and are achieved without the influence of solvent additives or postdeposition thermal annealing.

  DOI：

  10.1021/ja310483w
• 作为产物：
  描述：

  4,7-二溴-2,1,3-苯并噻二唑 、 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 在 四(三苯基膦)钯 作用下， 以 甲苯 为溶剂， 反应 1.33h， 以45%的产率得到5,5'-bis[4-(7-bromobenzo[2,1,3]thiadiazole)]-3,3'-bis(2-ethylhexyl)silylene-2,2'-bithiophene
  参考文献：
  名称：

  Solar Cell Efficiency, Self-Assembly, and Dipole–Dipole Interactions of Isomorphic Narrow-Band-Gap Molecules

  摘要：

  We examine the correlations of the dipole moment and conformational stability to the self-assembly and solar cell performance within a series of isomorphic, solution-processable molecules. These charge-transfer chromophores are described by a D-1-A-D-A-D-1 structure comprising electron-rich 2-hexylbithiophene and 3,3'-di-2-ethylhexylsilylene-2,2'-bithiophene moieties as the donor units D-1 and D, respectively. The building blocks 2,1,3-benzothiadiazole (BT) and [1,2,5]thiadiazolo[3,4-c]pyridine (PT) were used as the electron-deficient acceptor units A. Using a combination of UV-visible spectroscopy, field-effect transistors, solar cell devices, grazing incident wide-angle X-ray scattering, and transmission electron microscopy, three PT-containing compounds (1-3) with varying regiochemistry and symmetry, together with the BT-based compound 5,5'-bis{(4-(7-hexylthiophen-2-yl)thiophen-2-yl)-[1,2,5]thiadiazolobenzene}-3,3'-di-2-ethylhexylsilylene-2,2'-bithiophene (4), are compared and contrasted in solution, in thin films, and as blends with the electron acceptor [6,6]-phenyl-C-70-butyric acid methyl ester. The molecules with symmetric orientations of the PT acceptor, 1 and 2, yield highly ordered blended thin films. The best films, processed with the solvent additive 1,8-diiodooctane, show donor "crystallite" length scales on the order or 15-35 nm and photovoltaic power conversion efficiencies (PCEs) of 7.0 and 5.6%, respectively. Compound 3, with an unsymmetrical orientation of PT heterocycles, shows subtle differences in the crystallization behavior and a best PCE of 3.2%. In contrast, blends of the BT-containing donor 4 are highly disordered and give PCEs below 0.2%. We speculate that the differences in self-assembly arise from the strong influence of the BT acceptor and its orientation on the net dipole moment and geometric description of the chromophore.

  DOI：

  10.1021/ja3050713

文献信息

• Narrow-Band-Gap Conjugated Chromophores with Extended Molecular Lengths
  作者：Xiaofeng Liu、Yanming Sun、Louis A. Perez、Wen Wen、Michael F. Toney、Alan J. Heeger、Guillermo C. Bazan

  DOI：10.1021/ja310483w

  日期：2012.12.26

  The influence of extending the molecular length of donor acceptor chromophores on properties relevant to organic optoelectronic devices has been studied by using two new narrow-band-gap systems. Most significantly, we find that the higher molecular weight systems exhibit higher thermal stabilities (beyond 200 degrees C) when introduced into field effect transistor devices. It is also possible to fabricate bulk heterojunction solar cells using PC61BM with power conversion efficiencies >6%. These high values are not heavily influenced by the blend composition and are achieved without the influence of solvent additives or postdeposition thermal annealing.
• 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.
• Solar Cell Efficiency, Self-Assembly, and Dipole–Dipole Interactions of Isomorphic Narrow-Band-Gap Molecules
  作者：Christopher J. Takacs、Yanming Sun、Gregory C. Welch、Louis A. Perez、Xiaofeng Liu、Wen Wen、Guillermo C. Bazan、Alan J. Heeger

  DOI：10.1021/ja3050713

  日期：2012.10.10

  We examine the correlations of the dipole moment and conformational stability to the self-assembly and solar cell performance within a series of isomorphic, solution-processable molecules. These charge-transfer chromophores are described by a D-1-A-D-A-D-1 structure comprising electron-rich 2-hexylbithiophene and 3,3'-di-2-ethylhexylsilylene-2,2'-bithiophene moieties as the donor units D-1 and D, respectively. The building blocks 2,1,3-benzothiadiazole (BT) and [1,2,5]thiadiazolo[3,4-c]pyridine (PT) were used as the electron-deficient acceptor units A. Using a combination of UV-visible spectroscopy, field-effect transistors, solar cell devices, grazing incident wide-angle X-ray scattering, and transmission electron microscopy, three PT-containing compounds (1-3) with varying regiochemistry and symmetry, together with the BT-based compound 5,5'-bis(4-(7-hexylthiophen-2-yl)thiophen-2-yl)-[1,2,5]thiadiazolobenzene}-3,3'-di-2-ethylhexylsilylene-2,2'-bithiophene (4), are compared and contrasted in solution, in thin films, and as blends with the electron acceptor [6,6]-phenyl-C-70-butyric acid methyl ester. The molecules with symmetric orientations of the PT acceptor, 1 and 2, yield highly ordered blended thin films. The best films, processed with the solvent additive 1,8-diiodooctane, show donor "crystallite" length scales on the order or 15-35 nm and photovoltaic power conversion efficiencies (PCEs) of 7.0 and 5.6%, respectively. Compound 3, with an unsymmetrical orientation of PT heterocycles, shows subtle differences in the crystallization behavior and a best PCE of 3.2%. In contrast, blends of the BT-containing donor 4 are highly disordered and give PCEs below 0.2%. We speculate that the differences in self-assembly arise from the strong influence of the BT acceptor and its orientation on the net dipole moment and geometric description of the chromophore.