(4-(5-(2-ethylhexyl)thiophen-2-yl)-8-(5-(2-ethylpentyl)thiophen-2-yl)benzo[1,2-b:4,5-b']dithiophene-2,6-diyl)bis(tributylstannane) | 1439862-07-3

• 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: (4-(5-(2-ethylhexyl)thiophen-2-yl)-8-(5-(2-ethylpentyl)thiophen-2-yl)benzo[1,2-b:4,5-b']dithiophene-2,6-diyl)bis(tributylstannane)
• 英文别名: (4,8-bis(5-(2-ethylhexyl)-thiophen-2-yl)benzo[1,2-b:4,5-b′]dithiophene-2,6-diyl)bis-tributylstannane；(4,8-bis(5-(2-ethylhexyl)thiophen-2-yl)benzo[1,2-b:4,5-b'] dithiophene-2,6-diyl)bis(tributylstannane)；2,6-bis(tributyltin)-4,8-bis[5-(2-ethylhexyl)-2-thienyl]benzodithiophene
• CAS: 1439862-07-3
• 化学式: C₅₈H₉₄S₄Sn₂
• 分子量: 1157.07
• InChiKey: MUAKSCVOVFQAEE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  20.45
• 重原子数：
  64
• 可旋转键数：
  20
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  58.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-bromo-7-(4-hexylthiophen-2-yl)benzo[c][1,2,5]thiadiazole 、 (4-(5-(2-ethylhexyl)thiophen-2-yl)-8-(5-(2-ethylpentyl)thiophen-2-yl)benzo[1,2-b:4,5-b']dithiophene-2,6-diyl)bis(tributylstannane) 在 四(三苯基膦)钯 作用下， 以 甲苯 为溶剂， 反应 48.0h， 以34%的产率得到
  参考文献：
  名称：

  Synthesis, characterization and photovoltaic properties of benzo[1,2-b:4,5-b′]dithiophene-bridged molecules

  摘要：

  四种以苯并[1,2-b:4,5-b′]二噻吩（BDT）为中心的小分子被合成，它们具有不同的受体和端基团，作为有机太阳能电池的给体材料。

  DOI：

  10.1039/c4ra10081f
• 作为产物：
  描述：

  苯并[1,2-b:4,5-b']二噻吩-4,8-二酮 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 3.5h， 生成 (4-(5-(2-ethylhexyl)thiophen-2-yl)-8-(5-(2-ethylpentyl)thiophen-2-yl)benzo[1,2-b:4,5-b']dithiophene-2,6-diyl)bis(tributylstannane)
  参考文献：
  名称：

  Molecular electron-acceptors based on benzodithiophene for organic photovoltaics

  摘要：

  Two extended conjugated molecules potentially active as electron-acceptor materials for organic solar cells have been synthesized by grafting the electron-withdrawing dicyanovinyl (1) and p-cyano pyridyl (2) groups on the rigid and planar benzodithiophene (BDT) platform. UV Vis spectroscopy shows that both compounds absorb in the visible region of the solar spectrum. Cyclic voltammetry indicates that only compound 1 presents a LUMO level comparable to that of fullerene C-60. A preliminary evaluation of the potentialities of compound 1 as an electron-acceptor has been carried out on 'all-molecular' solution-processed bulk hetero-junction solar cells using a small triphenylamine-based system as the molecular donor. In spite of a high open-circuit voltage, the devices present a modest efficiency indicating that the light-harvesting properties and charge-mobility of the acceptor-molecules need further structural optimization. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.03.070

文献信息

• Significant Enhancement of Polymer Solar Cell Performance via Side-Chain Engineering and Simple Solvent Treatment
  作者：Yang Wang、Ying Liu、Shaojie Chen、Ruixiang Peng、Ziyi Ge

  DOI：10.1021/cm401618h

  日期：2013.8.13

  Rational design and synthesis of polymeric semiconductors is critical to the development of polymer solar cells (PSCs). In this work, a new series of benzodithiophene–difuranylbenzooxadiazole-based donor–acceptor co-polymers—namely, PBDT-DFBO, PBDTT-DFBO, and PBDTF-DFBO, with various side groups—have been developed for bulk-heterojunction PSCs. These side-group substituents provide the opportunity

  聚合物半导体的合理设计和合成对于聚合物太阳能电池（PSC）的开发至关重要。在这项工作中，针对本体-异质结PSC，开发了一系列新的基于苯并二噻吩-二呋喃基苯并恶二唑的供体-受体共聚物，即PBDT-DFBO，PBDTT-DFBO和PBDTF-DFBO，带有不同的侧基。这些侧基取代基提供了调整聚合物的光电性能的机会。另外，我们表明，可以通过用烷基噻吩基侧基与呋喃对应物取代来同时实现聚合物带隙的减少和装置中电荷迁移率的提高。在初步研究中，对于带有烷氧基侧链的PBDT-DFBO，人们可以获得功率转换效率（PCE）为2.1％的PSC，2。具有烷基噻吩基侧基的PBDTT-DFBO为2％，具有烷基呋喃基侧基的PBDTF-DFBO为3.0％。通过简单的溶剂处理进一步优化了器件的性能。基于PBDTF-DFBO：PC的PSC71 BM甚至可以达到7.0％的PCE，表现出130％的增强。据我们所知，7.0％的值是
• Solution-Processed and High-Performance Organic Solar Cells Using Small Molecules with a Benzodithiophene Unit
  作者：Jiaoyan Zhou、Yi Zuo、Xiangjian Wan、Guankui Long、Qian Zhang、Wang Ni、Yongsheng Liu、Zhi Li、Guangrui He、Chenxi Li、Bin Kan、Miaomiao Li、Yongsheng Chen

  DOI：10.1021/ja403318y

  日期：2013.6.12

  Three small molecules named DR3TBDTT, DR3TBDTT-HD, and DR3TBD2T with a benzo[1,2-b:4,5-b']dithiophene (BDT) unit as the central building block have been designed and synthesized for solution-processed bulk-heterojunction solar cells. Power conversion efficiencies (PCEs) of 8.12% (certified 7.61%) and 8.02% under AM 1.5G irradiation (100 mW cm(-2)) have been achieved for DR3TBDTT- and DR3TBDT2T-based

  已经设计并合成了三种名为 DR3TBDTT、DR3TBDTT-HD 和 DR3TBD2T 的小分子，其中苯并[1,2-b:4,5-b']二噻吩 (BDT) 单元作为中心结构单元，用于溶液处理的大容量-异质结太阳能电池。使用 PC71BM 作为基于 DR3TBDTT 和 DR3TBDT2T 的有机光伏器件 (OPV)，在 AM 1.5G 辐照 (100 mW cm(-2)) 下的功率转换效率 (PCE) 为 8.12%（经认证为 7.61%）和 8.02%接受者，分别。通过将传统小分子和聚合物的优点结合用于 OPV 的策略，通过提高短路电流密度而不牺牲高开路电压和填充因子来实现更好的 PCE。
• Stable organic dyes based on the benzo[1,2-b:4,5-b′]dithiophene donor for efficient dye-sensitized solar cells
  作者：Yi-Fan Chen、Jun-Min Liu、Jian-Feng Huang、Li-Lin Tan、Yong Shen、Li-Min Xiao、Dai-Bin Kuang、Cheng-Yong Su

  DOI：10.1039/c5ta00332f

  日期：——

  A stable sensitizer incorporating the benzo[1,2-b:4,5-b′]dithiophene donor was used in dye-sensitized solar cells, showing the highest efficiency reported for amine-free organic dyes.

  一种稳定的敏化剂，包含苯并[1,2-b:4,5-b′]噻吩给体，被用于染料敏化太阳能电池中，显示出无胺有机染料中报告的最高效率。
• Hydrophobic Hole-Transporting Materials Incorporating Multiple Thiophene Cores with Long Alkyl Chains for Efficient Perovskite Solar Cells
  作者：Pei-Yang Su、Yi-Fan Chen、Jun-Min Liu、Li-Min Xiao、Dai-Bin Kuang、Marcel Mayor、Cheng-Yong Su

  DOI：10.1016/j.electacta.2016.05.122

  日期：2016.8

  structure-property relationships of these HTMs for perovskite solar cells have been systematically investigated. It is found that introducing hydrophobic alkyl chains into HTMs can retard interfacial charge recombination and, specifically, improve stability owing to the enhanced moisture resistance. Perovskite solar cells based on SP-01 give an overall conversion efficiency of 12.37% without, and 13.91% with the

  两种带有5,7-双（3-己基噻吩-2-基）-2,3-二氢噻吩并[3,4-b] [1,4]二恶英的噻吩核的疏水空穴传输材料（HTM）（用于SP- 01）或4,8-双（5-（2-（乙基乙基己基）噻吩-2-基）苯并[1,2-b：4,5-b']二噻吩（对于SP-02）和长烷基取代基通过空穴转移分子2,5-双（4,4'-双（甲氧基苯基）氨基酚-4''-基）-3,4-乙撑二氧噻吩（H101）作为参考化合物。已经对钙钛矿型太阳能电池的这些HTM的结构性质关系进行了系统研究。已经发现，将疏水性烷基链引入HTM可以延迟界面电荷的重组，并且由于增强的耐湿性而特别地提高了稳定性。基于SP-01的钙钛矿太阳能电池在不添加FK102的情况下的总转换效率为12.37％，在添加FK102的情况下的总转换效率为13.91％。这些值比H101（11.59％）更好，并且与标准spiro-OMeTAD（12.95％）相当。此外，基于疏水性HTM
• Molecular electron-acceptors based on benzodithiophene for organic photovoltaics
  作者：Yue Jiang、Clément Cabanetos、Magali Allain、Ping Liu、Jean Roncali

  DOI：10.1016/j.tetlet.2015.03.070

  日期：2015.4

  Two extended conjugated molecules potentially active as electron-acceptor materials for organic solar cells have been synthesized by grafting the electron-withdrawing dicyanovinyl (1) and p-cyano pyridyl (2) groups on the rigid and planar benzodithiophene (BDT) platform. UV Vis spectroscopy shows that both compounds absorb in the visible region of the solar spectrum. Cyclic voltammetry indicates that only compound 1 presents a LUMO level comparable to that of fullerene C-60. A preliminary evaluation of the potentialities of compound 1 as an electron-acceptor has been carried out on 'all-molecular' solution-processed bulk hetero-junction solar cells using a small triphenylamine-based system as the molecular donor. In spite of a high open-circuit voltage, the devices present a modest efficiency indicating that the light-harvesting properties and charge-mobility of the acceptor-molecules need further structural optimization. (C) 2015 Elsevier Ltd. All rights reserved.