4,5-dioctyloxybenzo[1,2-b:4,3-b']dithiophene | 1174653-36-1

• 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-dioctyloxybenzo[1,2-b:4,3-b']dithiophene
• 英文别名: 7,8-dioctyloxybenzo[1,2-b:4,3-b']dithiophene；BDT-Oct；4,5-Dioctoxythieno[3,2-e][1]benzothiole；4,5-dioctoxythieno[3,2-e][1]benzothiole
• CAS: 1174653-36-1
• 化学式: C₂₆H₃₈O₂S₂
• 分子量: 446.719
• InChiKey: YAGLAMKCXSOVNA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.7
• 重原子数：
  30
• 可旋转键数：
  16
• 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-dioctyloxybenzo[1,2-b:4,3-b']dithiophene 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以65%的产率得到2,7-dibromo-4,5-dioctyloxybenzo[1,2-b:4,3-b']dithiophene
  参考文献：
  名称：

  Interchain interactions in poly(benzo[1,2-b:4,3-b′]dithiophene)s and the effect of substituents on aggregation

  摘要：

  使用科隆/凯尔西和铃木聚合方法合成了两种具有线性和支链取代基的聚（苯并[1,2-b:4,3-b²]二噻吩）[PBDT]，它们是可自由溶解的聚合物（分子量：6.6-12.7 kDa，DP：15-29）。具有线性取代基的聚合物表现出聚合体聚集增加的效果，这可以从浴色光谱带中得到证实。电化学结果还显示了链间相互作用的影响，其中线性衍生物的聚集体在比支链衍生物低0.5 V的电压下发生氧化过程。

  DOI：

  10.1039/b820002e
• 作为产物：
  描述：

  1-碘辛烷 、 4,5-diacetoxybenzo[1,2-b:4,3-b']dithiophene 在 caesium carbonate 作用下， 以 乙腈 为溶剂， 反应 72.0h， 以90%的产率得到4,5-dioctyloxybenzo[1,2-b:4,3-b']dithiophene
  参考文献：
  名称：

  Synthesis and Characterization of Dioctyloxybenzo[1,2-b:4,3-b′]dithiophene-Containing Copolymers for Polymer Solar Cells

  摘要：

  A series of D-A copolymers containing dioctyloxybenzo[1,2-b:4,3-b']dithiophene (BdT) donor unit and different acceptor unit of bithiazole (BTz), thiazolo[5,4-d]-thiazole (TTz), dithienylylbenzothiadiazole (DTBT), and dithienyl-pyrrolo[3,4-c]pyrrole-1,4-dione (DPP), PBdT-BTz, PBdT-TTz, PBdT-DTBT, and PBdT-DPP, were synthesized for the application as donor materials in polymer solar cells (PSCs). Bandgaps and HOMO (the highest occupied molecular orbital) energy levels of the copolymers were tuned effectively by using different acceptor units from 2.01 and -5.16 eV for PBdT-BTz, to 1.91 and -5.19 eV for PBdT-TTz, 1.70 and -5.09 eV for PBdT-DTBT, and 1.41 and -5.01 eV for PBdT-DPP. The PSCs based on the blend of PBdT-TTz (with a lower HOMO of -5.19 eV) and PC70BM (1:3 w/w) exhibited a power conversion efficiency of 3.40% with a J(sc) of 5.50 mA/cm(2), a high V-oc of 0.90 V, and a high FF of 68.7%.

  DOI：

  10.1021/ma201565f

文献信息

• Interchain interactions in poly(benzo[1,2-b:4,3-b′]dithiophene)s and the effect of substituents on aggregation
  作者：Robert N. Brookins、Erik Berda、John R. Reynolds

  DOI：10.1039/b820002e

  日期：——

  Two poly(benzo[1,2-b:4,3-b′]dithiophene)s [PBDTs] with linear and branched substituents have been synthesized as freely soluble polymers using Colon/Kelsey and Suzuki polymerizations (Mn = 6.6–12.7 kDa, DP: 15–29). Polymers with linear substituents show effects due to increased polymer aggregation as evidenced bathochromic spectral bands. The electrochemical results also show the influence of interchain interactions where the aggregate of the linear derivative has oxidative processes at 0.5 V lower potentials than the branched derivative.

  使用科隆/凯尔西和铃木聚合方法合成了两种具有线性和支链取代基的聚（苯并[1,2-b:4,3-b²]二噻吩）[PBDT]，它们是可自由溶解的聚合物（分子量：6.6-12.7 kDa，DP：15-29）。具有线性取代基的聚合物表现出聚合体聚集增加的效果，这可以从浴色光谱带中得到证实。电化学结果还显示了链间相互作用的影响，其中线性衍生物的聚集体在比支链衍生物低0.5 V的电压下发生氧化过程。
• Synthesis and Characterization of Dioctyloxybenzo[1,2-<i>b</i>:4,3-<i>b</i>′]dithiophene-Containing Copolymers for Polymer Solar Cells
  作者：Maojie Zhang、Yeping Sun、Xia Guo、Chaohua Cui、Youjun He、Yongfang Li

  DOI：10.1021/ma201565f

  日期：2011.10.11

  A series of D-A copolymers containing dioctyloxybenzo[1,2-b:4,3-b']dithiophene (BdT) donor unit and different acceptor unit of bithiazole (BTz), thiazolo[5,4-d]-thiazole (TTz), dithienylylbenzothiadiazole (DTBT), and dithienyl-pyrrolo[3,4-c]pyrrole-1,4-dione (DPP), PBdT-BTz, PBdT-TTz, PBdT-DTBT, and PBdT-DPP, were synthesized for the application as donor materials in polymer solar cells (PSCs). Bandgaps and HOMO (the highest occupied molecular orbital) energy levels of the copolymers were tuned effectively by using different acceptor units from 2.01 and -5.16 eV for PBdT-BTz, to 1.91 and -5.19 eV for PBdT-TTz, 1.70 and -5.09 eV for PBdT-DTBT, and 1.41 and -5.01 eV for PBdT-DPP. The PSCs based on the blend of PBdT-TTz (with a lower HOMO of -5.19 eV) and PC70BM (1:3 w/w) exhibited a power conversion efficiency of 3.40% with a J(sc) of 5.50 mA/cm(2), a high V-oc of 0.90 V, and a high FF of 68.7%.