5',5''-(4-(heptadecan-9-yl)-4H-dithieno[3,2-b:2',3'-d]pyrrole-2,6-diyl)di-2',2''-bithiophene-5-carbaldehyde | 1265622-25-0

• 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: 5',5''-(4-(heptadecan-9-yl)-4H-dithieno[3,2-b:2',3'-d]pyrrole-2,6-diyl)di-2',2''-bithiophene-5-carbaldehyde
• CAS: 1265622-25-0
• 化学式: C₄₃H₄₇NO₂S₆
• 分子量: 802.248
• InChiKey: VXBMTSFVKFKCKM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  16.5
• 重原子数：
  52.0
• 可旋转键数：
  21.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  39.07
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  5',5''-(4-(heptadecan-9-yl)-4H-dithieno[3,2-b:2',3'-d]pyrrole-2,6-diyl)di-2',2''-bithiophene-5-carbaldehyde 、 氰乙酸 在 ammonium acetate 、 溶剂黄146 作用下， 反应 36.0h， 以88.2%的产率得到(2E,2'E)-3,3'-(5',5''-(4-(heptadecan-9-yl)-4H-dithieno[3,2-b:2',3'-d]pyrrole-2,6-diyl)bis(2',2''-bithiophene-5',5'-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) 、 四(三苯基膦)钯 、 正丁基锂 、 potassium carbonate 、 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 60.75h， 生成 5',5''-(4-(heptadecan-9-yl)-4H-dithieno[3,2-b:2',3'-d]pyrrole-2,6-diyl)di-2',2''-bithiophene-5-carbaldehyde
  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

文献信息

• Effects of bridging atom in donor units and nature of acceptor groups on physical and photovoltaic properties of A-π-D-π-A oligomers
  作者：Jie Min、Yuriy N. Luponosov、Dmitry A. Khanin、Petr V. Dmitryakov、Evgeniya A. Svidchenko、Svetlana M. Peregudova、Linda Grodd、Souren Grigorian、Sergei N. Chvalun、Sergei A. Ponomarenko、Christoph J. Brabec

  DOI：10.1016/j.orgel.2017.12.052

  日期：2018.4

  A-π-D-π-A oligomers bearing either electron-donating dithieno[3,2-b:2′,3′-d]silole (DTS) or dithieno[3,2-b:2′,3′-d]pyrrole (DTP) units linked through a bithiophene π-bridge with the electron-withdrawing methyldicyanovinyl (DCV) or N-ethylrhodanine (Rh) groups is described. In order to evaluate the effects of different donor-acceptor combinations on various physical properties of the oligomers they are

  带有电子给体双噻吩并[3,2- b：2'，3'- d ]硅酮（DTS）或双噻吩并[3,2- b ]的一系列新型A-π-D-π-A低聚物的合成：2′，3′- d描述了通过联噻吩π桥与吸电子的甲基二氰基乙烯基（DCV）或N-乙基罗丹宁（Rh）基团连接的]吡咯（DTP）单元。为了评估不同供体-受体组合对低聚物各种物理性质的影响，已通过紫外可见光谱，差示扫描量热法（DSC），热重分析（TGA）和循环伏安法（CV）对其进行了全面研究。用DTP代替DTS以及用Rh代替DCV分别导致HOMO能级增加和LUMO能级稍微降低。与基于DTS的类似物相比，基于DTP的低聚物具有吸收光谱的红移和增加的溶解度。用Rh取代受体DCV单元也会显着提高溶解度，但是Rh基低聚物表现出较弱的分子间相互作用，较弱的太阳光吸收率以及较低的共混物中的载流子迁移率。总而言之，DTS-DCV和DTP-DCV共混物在退火后的结构改进与有