benzo[1,2-b:4,5-b]bis(4,4’-dihexyl-4H-silolo[3,2-b]thiophene-2,2’-diyl)bis(6-fluoro-4-(5'-hexyl-[2,2'-bithiophen]-5-yl)benzo[c][1,2,5]thiadiazole) | 1569453-41-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 双噻吩和低聚噻吩
• 英文名称: benzo[1,2-b:4,5-b]bis(4,4’-dihexyl-4H-silolo[3,2-b]thiophene-2,2’-diyl)bis(6-fluoro-4-(5'-hexyl-[2,2'-bithiophen]-5-yl)benzo[c][1,2,5]thiadiazole)
• 英文别名: 4,4'-(4,4,9,9-Tetrahexyl-4,9-dihydrobenzo[1'',2'':4,5;4'',5'':4',5']bissilolo[3,2-b:3',2'-b']dithiophene-2,7-diyl)bis[5-fluoro-7-(5'-hexyl[2,2'-bithiophen]-5-yl)-2,1,3-benzothiadiazole]；5-fluoro-4-[15-[5-fluoro-7-[5-(5-hexylthiophen-2-yl)thiophen-2-yl]-2,1,3-benzothiadiazol-4-yl]-9,9,18,18-tetrahexyl-5,14-dithia-9,18-disilapentacyclo[10.6.0.03,10.04,8.013,17]octadeca-1(12),2,4(8),6,10,13(17),15-heptaen-6-yl]-7-[5-(5-hexylthiophen-2-yl)thiophen-2-yl]-2,1,3-benzothiadiazole
• CAS: 1569453-41-3
• 化学式: C₇₈H₉₂F₂N₄S₈Si₂
• 分子量: 1436.31
• InChiKey: UBXQUHUVSJDOAN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  26.0
• 重原子数：
  94
• 可旋转键数：
  36
• 环数：
  13.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  278
• 氢给体数：
  0
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  4-溴-5-氟-7-(5'-己基-[2,2'-联噻吩]-5-基)苯并[C][1,2,5]噻二唑 、 2,7-双三甲基锡-苯并[1,2-B:4,5-B]双(4,4'-二辛基-4H-二噻吩并噻咯)-双三甲基锡 在 四(三苯基膦)钯 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以66%的产率得到benzo[1,2-b:4,5-b]bis(4,4’-dihexyl-4H-silolo[3,2-b]thiophene-2,2’-diyl)bis(6-fluoro-4-(5'-hexyl-[2,2'-bithiophen]-5-yl)benzo[c][1,2,5]thiadiazole)
  参考文献：
  名称：

  Silaindacenodithiophene-Based Molecular Donor: Morphological Features and Use in the Fabrication of Compositionally Tolerant, High-Efficiency Bulk Heterojunction Solar Cells

  摘要：

  A novel solution-processable small molecule, namely, benzo[1,2-b:4,5-b]bis(4,4'-dihexyl-4H-silolo[3,2-b]-thiophene-2,2'-diyl)bis(6-fluoro-4-(5'-hexyl-[2,2'-bithiophene]-5-yl)benzo[c][1,2,5]thiadiazole (p-SIDT(FBTTh2)(2)), was designed and synthesized by utilizing the silaindacenodithiophene (SIDT) framework as the central D-2 donor unit within the D(1)AD(2)AD(1) chromophore configuration. Relative to the widely studied 7,7'-[4,4-bis(2-ethylhexyl)-4H-silolo[3,2-b:4,5-b']dithiophene-2,6-diyl]bis [6-fluoro-4-(5'-hexyl-[2,2 '-bithiophene]-5-yl)benzo[c][1,2,5]thiadiazole] (p-DTS(FBTTh2)(2)), which contains the stronger donor fragment clithienosilole (DTS) as D-2, one finds that p-SIDT(FBTTh2)(2) exhibits a wider band gap and can be used to fabricate bulk heterojunction solar cells with higher open circuit voltage (0.91 V). Most remarkably, thin films comprising p-SIDT(FBTTh2)(2) can achieve exceptional levels of self-organization directly via solution deposition. For example, high-resolution transmission electron microscopy analysis shows that p-SIDT(FBTTh2)(2) spin-cast from chlorobenzene organizes into crystalline domains with lattice planes that extend over length scales on the order of hundreds of nanometers. Such features suggest liquid crystalline properties during the evolution of the film. Moreover, grazing incidence wide-angle X-ray scattering analysis shows a strong tendency for the molecules to exist with a strong "face-on" orientation relative to the substrate plane. Similar structural features, albeit of more restricted dimensions, can be observed within p-SIDT(FBTTh2)(2):PC7IBM bulk heterojunction thin films when the films are processed with 0.4% diiodooctane (DIO) solvent additive. DIO use also increases the solar cell power conversion efficiencies (PCEs) from 1.7% to 6.4%. Of significance from a practical device fabrication perspective is that, for p-SIDT(FBTTh2)(2):PC71BM blends, there is a wide range of compositions (from 20:80 to 70:30 p-SIDT(FBTTh2)(2):PC71BM) that provide good photovoltaic response, i.e., PCE = 4-6%, indicating a robust tendency to form the necessary continuous phases for charge carrier collection. Light intensity photocurrent measurements, charge selective diode fabrication, and internal quantum efficiency determinations were carried out to obtain insight into the mechanism of device operation. Inclusion of DIO in the casting solution results in films that exhibit much lower photocurrent dependence on voltage and a concomitant increase in fill factor. At the optimum blend ratio, devices show high charge carrier mobilities, while mismatched hole and electron mobilities in blends with high or low donor content result in reduced fill factors and device performance.

  DOI：

  10.1021/ja412473p

文献信息

• Effects of solvent additive on “s-shaped” curves in solution-processed small molecule solar cells
  作者：John A Love、Shu-Hua Chou、Ye Huang、Guilllermo C Bazan、Thuc-Quyen Nguyen

  DOI：10.3762/bjoc.12.249

  日期：——

  A novel molecular chromophore, p-SIDT(FBTThCA8)₂, is introduced as an electron-donor material for bulk heterojunction (BHJ) solar cells with broad absorption and near ideal energy levels for the use in combination with common acceptor materials. It is found that films cast from chlorobenzene yield devices with strongly s-shaped current–voltage curves, drastically limiting performance. We find that addition of the common solvent additive diiodooctane, in addition to facilitating crystallization, leads to improved vertical phase separation. This yields much better performing devices, with improved curve shape, demonstrating the importance of morphology control in BHJ devices and improving the understanding of the role of solvent additives.

  介绍了一种新型分子色团p-SIDT（FBTThCA8）2作为电子给体材料，用于与常见受体材料结合的大面积异质结（BHJ）太阳能电池，具有广泛的吸收和接近理想能级。研究发现，用氯苯溶液制备的薄膜会产生强烈的S形电流-电压曲线，严重限制了性能。我们发现，添加常用的溶剂添加剂二碘辛烷不仅有助于结晶，而且导致垂直相分离的改善。这产生了性能更好的设备，改善了曲线形状，证明了在BHJ设备中控制形态的重要性，并提高了溶剂添加剂的作用的理解。
• Silaindacenodithiophene-Based Molecular Donor: Morphological Features and Use in the Fabrication of Compositionally Tolerant, High-Efficiency Bulk Heterojunction Solar Cells
  作者：John A. Love、Ikuhiro Nagao、Ye Huang、Martijn Kuik、Vinay Gupta、Christopher J. Takacs、Jessica E. Coughlin、Li Qi、Thomas S. van der Poll、Edward J. Kramer、Alan J. Heeger、Thuc-Quyen Nguyen、Guillermo C. Bazan

  DOI：10.1021/ja412473p

  日期：2014.3.5

  A novel solution-processable small molecule, namely, benzo[1,2-b:4,5-b]bis(4,4'-dihexyl-4H-silolo[3,2-b]-thiophene-2,2'-diyl)bis(6-fluoro-4-(5'-hexyl-[2,2'-bithiophene]-5-yl)benzo[c][1,2,5]thiadiazole (p-SIDT(FBTTh2)(2)), was designed and synthesized by utilizing the silaindacenodithiophene (SIDT) framework as the central D-2 donor unit within the D(1)AD(2)AD(1) chromophore configuration. Relative to the widely studied 7,7'-[4,4-bis(2-ethylhexyl)-4H-silolo[3,2-b:4,5-b']dithiophene-2,6-diyl]bis [6-fluoro-4-(5'-hexyl-[2,2 '-bithiophene]-5-yl)benzo[c][1,2,5]thiadiazole] (p-DTS(FBTTh2)(2)), which contains the stronger donor fragment clithienosilole (DTS) as D-2, one finds that p-SIDT(FBTTh2)(2) exhibits a wider band gap and can be used to fabricate bulk heterojunction solar cells with higher open circuit voltage (0.91 V). Most remarkably, thin films comprising p-SIDT(FBTTh2)(2) can achieve exceptional levels of self-organization directly via solution deposition. For example, high-resolution transmission electron microscopy analysis shows that p-SIDT(FBTTh2)(2) spin-cast from chlorobenzene organizes into crystalline domains with lattice planes that extend over length scales on the order of hundreds of nanometers. Such features suggest liquid crystalline properties during the evolution of the film. Moreover, grazing incidence wide-angle X-ray scattering analysis shows a strong tendency for the molecules to exist with a strong "face-on" orientation relative to the substrate plane. Similar structural features, albeit of more restricted dimensions, can be observed within p-SIDT(FBTTh2)(2):PC7IBM bulk heterojunction thin films when the films are processed with 0.4% diiodooctane (DIO) solvent additive. DIO use also increases the solar cell power conversion efficiencies (PCEs) from 1.7% to 6.4%. Of significance from a practical device fabrication perspective is that, for p-SIDT(FBTTh2)(2):PC71BM blends, there is a wide range of compositions (from 20:80 to 70:30 p-SIDT(FBTTh2)(2):PC71BM) that provide good photovoltaic response, i.e., PCE = 4-6%, indicating a robust tendency to form the necessary continuous phases for charge carrier collection. Light intensity photocurrent measurements, charge selective diode fabrication, and internal quantum efficiency determinations were carried out to obtain insight into the mechanism of device operation. Inclusion of DIO in the casting solution results in films that exhibit much lower photocurrent dependence on voltage and a concomitant increase in fill factor. At the optimum blend ratio, devices show high charge carrier mobilities, while mismatched hole and electron mobilities in blends with high or low donor content result in reduced fill factors and device performance.