4,5-bis(2-ethylhexyl)benzo[1,2-b:6,5-b’]dithiophene | 1256165-40-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: 4,5-bis(2-ethylhexyl)benzo[1,2-b:6,5-b’]dithiophene
• 英文别名: 4,5-di(2-ethylhexyloxy)benzo[2,1-b:3,4-b']dithiophene；4,5-Bis(2-ethylhexoxy)thieno[3,2-g][1]benzothiole
• CAS: 1256165-40-8
• 化学式: C₂₆H₃₈O₂S₂
• 分子量: 446.719
• InChiKey: IXMAVULTWDMCAW-UHFFFAOYSA-N

物化性质

• 沸点：
  548.6±45.0 °C(Predicted)
• 密度：
  1.072±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  10.2
• 重原子数：
  30
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  74.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4,5-bis(2-ethylhexyl)benzo[1,2-b:6,5-b’]dithiophene 、 三甲基氯化锡 在 正丁基锂 作用下， 以80%的产率得到2,7-bis(trimethyltin)-4,5-di(2-ethylhexyloxy)benzo[2,1-b:3,4-b']dithiophene
  参考文献：
  名称：

  新型苯并二噻吩稠合的per二酰亚胺受体的合成和表征：通过结构异构性调节光伏性能

  摘要：

  通过per二酰亚胺（PDI）受体与两个异构苯并二噻吩供体核心（包括苯并[2,1- b]）之间的光诱导闭环反应，设计并合成了两个异构的苯并二噻吩稠合的per二酰亚胺BPDI-1和BPDI-2：3,4- b' ]二噻吩（BDP）和苯并[1,2- b：4,3- b' ]二噻吩（BdT）。比较研究了结构异构对分子几何结构，吸收，能级，薄膜形态以及光伏性能的影响。发现供体核中S原子取代位置的变化导致新开发的分子具有不同的分子几何形状BPDI-1和BPDI-2受体。与含BDP的BPDI-1相比，BdT核的掺入使BPDI-2具有显着增强的主链畸变。当与市售的聚合物供体（PTB7-Th）共混时，BPDI-2受体的这种扭曲结构特征在减少分子聚集中起关键作用，这有助于有效地提高短路电流密度和光伏效率。其结果是，非富勒烯太阳能电池制造从BPDI-2受体实现更高的光电转换效率（4.44％）显着的BPDI-1（2.

  DOI：

  10.1016/j.dyepig.2019.04.027
• 作为产物：
  描述：

  2,7-bis(trimethylsilyl)benzo[1,2-b:6,5-b']dithiophene-4,5-dione 在 硫酸 、 caesium carbonate 、 三乙胺 、 锌 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 72.0h， 生成 4,5-bis(2-ethylhexyl)benzo[1,2-b:6,5-b’]dithiophene
  参考文献：
  名称：

  Efficient Synthesis of Benzo[1,2-b:6,5-b′]dithiophene-4,5-dione (BDTD) and Its Chemical Transformations into Precursors for π-Conjugated Materials

  摘要：

  A straightforward synthesis of the fused-aromatic dione benzo[1,2-b:6,5-b']dithiophene-4,5-dione (BDTD) has been developed. This fused-aromatic dione was subjected to various chemical transformations to generate diverse molecules with potential use in pi-conjugated materials for organic electronics.

  DOI：

  10.1021/ol302704v

文献信息

• Correlation of intermolecular packing distance and crystallinity of D-A polymers according to π-spacer for polymer solar cells
  作者：Tae Ho Lee、Min Hee Choi、Sung Jae Jeon、Doo Kyung Moon

  DOI：10.1016/j.polymer.2016.07.082

  日期：2016.9

  Donor-acceptor-type polymers, PBDPBT-T, PBDPBT-TT, and PBDPBT-biT, were polymerized via Stille coupling reactions. In the unfavorable mode of DFT calculations, the distance between BDP in the two different polymer main chains showed different distance of repeating unit (Dn) according to the pi-spacers type. Especially, PBDPBT-TT caused larger D2 than PBDPBT-T and PBDPBT-biT. The UV-vis absorption spectra of PBDPBT-T and PBDPBT-biT films were red-shifted compared with the solution absorption, whereas that of a PBDPBT-TT film was blue-shifted. PBDPBT-T and PBDPBT-biT had high crystallinity and a tendency of face-on orientation. In contrast, PBDPBT-TT had low crystallinity. Owing to differences in packing formation, the polymers had different J(SC) values. When a polymer solar cell device was fabricated through a solution process, PBDPBT-biT (in a 1:1.5 ratio with PC70BM) exhibited a PCE of 4.50%, with a J(SC) value of 8.6 mA/cm(2), a V-OC value of 0.88 V, and an FF value of 59.4%. (C) 2016 Elsevier Ltd. All rights reserved.
• DIKETOPYRROLOPYRROLE POLYMERS FOR USE IN ORGANIC SEMICONDUCTOR DEVICES
  申请人：BASF SE

  公开号：EP2435500B1

  公开（公告）日：2019-10-30
• Efficient Synthesis of Benzo[1,2-<i>b</i>:6,5-<i>b</i>′]dithiophene-4,5-dione (BDTD) and Its Chemical Transformations into Precursors for π-Conjugated Materials
  作者：Frank A. Arroyave、Coralie A. Richard、John R. Reynolds

  DOI：10.1021/ol302704v

  日期：2012.12.21

  A straightforward synthesis of the fused-aromatic dione benzo[1,2-b:6,5-b']dithiophene-4,5-dione (BDTD) has been developed. This fused-aromatic dione was subjected to various chemical transformations to generate diverse molecules with potential use in pi-conjugated materials for organic electronics.
• Synthesis and characterization of novel benzodithiophene-fused perylene diimide acceptors: Regulate photovoltaic performance via structural isomerism
  作者：Xiaolin Li、Kaile Wu、Liping Zheng、Yihua Deng、Songting Tan、Huajie Chen

  DOI：10.1016/j.dyepig.2019.04.027

  日期：2019.9

  BPDI-2, are designed and synthesized via photo-induced ring-closure reaction between perylene diimide (PDI) acceptor and both isomeric benzodithiophene donor cores, including benzo[2,1-b:3,4-b']dithiophene (BDP) and benzo[1,2-b:4,3-b']dithiophene (BdT). The effect of structural isomerism on the molecular geometry, absorption, energy level, film morphology as well as photovoltaic performance is comparatively

  通过per二酰亚胺（PDI）受体与两个异构苯并二噻吩供体核心（包括苯并[2,1- b]）之间的光诱导闭环反应，设计并合成了两个异构的苯并二噻吩稠合的per二酰亚胺BPDI-1和BPDI-2：3,4- b' ]二噻吩（BDP）和苯并[1,2- b：4,3- b' ]二噻吩（BdT）。比较研究了结构异构对分子几何结构，吸收，能级，薄膜形态以及光伏性能的影响。发现供体核中S原子取代位置的变化导致新开发的分子具有不同的分子几何形状BPDI-1和BPDI-2受体。与含BDP的BPDI-1相比，BdT核的掺入使BPDI-2具有显着增强的主链畸变。当与市售的聚合物供体（PTB7-Th）共混时，BPDI-2受体的这种扭曲结构特征在减少分子聚集中起关键作用，这有助于有效地提高短路电流密度和光伏效率。其结果是，非富勒烯太阳能电池制造从BPDI-2受体实现更高的光电转换效率（4.44％）显着的BPDI-1（2.