4-(heptadecan-9-yl)-2,6-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-4H-dithieno[3,2-b:2',3'-d]pyrrole | 1265622-23-8

• 物质功能分类: 医药中间体 - 噻吩类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 4-(heptadecan-9-yl)-2,6-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-4H-dithieno[3,2-b:2',3'-d]pyrrole
• CAS: 1265622-23-8
• 化学式: C₃₇H₆₁B₂NO₄S₂
• 分子量: 669.65
• InChiKey: BBIIOAPLYVMQKN-UHFFFAOYSA-N

物化性质

• 沸点：
  691.9±55.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  10.56
• 重原子数：
  46.0
• 可旋转键数：
  17.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  41.85
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  4-(heptadecan-9-yl)-2,6-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-4H-dithieno[3,2-b:2',3'-d]pyrrole 在 四(三苯基膦)钯 、 ammonium acetate 、 potassium carbonate 、 溶剂黄146 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 72.0h， 生成 (2E,2'E)-3,3'-(5,5'-(4-(heptadecan-9-yl)-4H-dithieno[3,2-b:2',3'-d]pyrrole-2,6-diyl)bis(thiophene-5,2-diyl))bis(2-cyanoacrylic acid)
  参考文献：
  名称：

  Synthesis and applications of novel acceptor–donor–acceptor organic dyes with dithienopyrrole- and fluorene-cores for dye-sensitized solar cells

  摘要：

  Four novel symmetrical organic dyes (S1-S4) configured with acceptor-donor-acceptor (A-D-A) structures containing electron donating fluorene (S1 and S2) and N-alkyl dithieno[3,2-b:2',3'-d]pyrrole (DTP) (S3 and S4) cores terminated with two anchoring cyanoacrylic acids (as electron acceptors) were synthesized and applied to dye-sensitized solar cells (DSSCs). The DSSC device based on S2 dye showed the best photovoltaic performance among S1-S4 dyes: a maximum monochromatic incident photon-to-current conversion efficiency (IPCE) of 76%, a short circuit current (J(SC)) of 12.27 mA/cm(2), an open circuit voltage (V-OC) of 0.61 V. a fill factor (FF) of 0.63, and an overall power conversion efficiency (eta) of 4.73%. Besides, the utilization of chenodoxycholic acid (CDCA) as a co-adsorbent in the DSSC device based on S3 dye showed a significant improvement in its eta value (from 3.70% to 4.31%), which is attributed to the suppression of dye aggregation on TiO2 surface and thus to increase the J(SC) value eventually. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.11.044
• 作为产物：
  描述：

  2-(heptadecan-9-yl)isoindoline-1,3-dione 在 tris-(dibenzylideneacetone)dipalladium(0) 、 正丁基锂 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 、 一水合肼 、 sodium t-butanolate 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 、 甲苯 为溶剂， 反应 24.75h， 生成 4-(heptadecan-9-yl)-2,6-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-4H-dithieno[3,2-b:2',3'-d]pyrrole
  参考文献：
  名称：

  Synthesis and applications of novel acceptor–donor–acceptor organic dyes with dithienopyrrole- and fluorene-cores for dye-sensitized solar cells

  摘要：

  Four novel symmetrical organic dyes (S1-S4) configured with acceptor-donor-acceptor (A-D-A) structures containing electron donating fluorene (S1 and S2) and N-alkyl dithieno[3,2-b:2',3'-d]pyrrole (DTP) (S3 and S4) cores terminated with two anchoring cyanoacrylic acids (as electron acceptors) were synthesized and applied to dye-sensitized solar cells (DSSCs). The DSSC device based on S2 dye showed the best photovoltaic performance among S1-S4 dyes: a maximum monochromatic incident photon-to-current conversion efficiency (IPCE) of 76%, a short circuit current (J(SC)) of 12.27 mA/cm(2), an open circuit voltage (V-OC) of 0.61 V. a fill factor (FF) of 0.63, and an overall power conversion efficiency (eta) of 4.73%. Besides, the utilization of chenodoxycholic acid (CDCA) as a co-adsorbent in the DSSC device based on S3 dye showed a significant improvement in its eta value (from 3.70% to 4.31%), which is attributed to the suppression of dye aggregation on TiO2 surface and thus to increase the J(SC) value eventually. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.11.044