5-ethyl-10,10-dioctyl-2,8-di(thiophen-2-yl)-5,10-dihydroindeno[1,2-b]indole | 1450985-82-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 5-ethyl-10,10-dioctyl-2,8-di(thiophen-2-yl)-5,10-dihydroindeno[1,2-b]indole
• CAS: 1450985-82-6
• 化学式: C₄₁H₅₁NS₂
• 分子量: 621.995
• InChiKey: KPHNDNAIOKHIBR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.89
• 重原子数：
  44.0
• 可旋转键数：
  17.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  4.93
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  5-ethyl-10,10-dioctyl-2,8-di(thiophen-2-yl)-5,10-dihydroindeno[1,2-b]indole 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41%的产率得到2,8-bis(5-bromothiophen-2-yl)-5-ethyl-10,10-dioctyl-5,10-dihydroindeno[1,2-b]indole
  参考文献：
  名称：

  Synthesis and characterization of new indeno[1,2-b]indole-co-benzothiadiazole-based π-conjugated ladder type polymers for bulk heterojunction polymer solar cells

  摘要：

  We have developed a new ladder type, tetrafused, pi-conjugated building block with indeno[1,2-b]indole (II) and extended the pi-conjugation of the indeno[1,2-b]indole ring by incorporating a thiophene it-spacer in the 2nd and 8th positions to attain dithiophene-substituted indeno[1,2-b]indole (IIDT). The two newly synthesized donor monomers II and IIDT were polymerized with 2,1,3-benzothiadiazole (BT) acceptor to obtain poly[4-(5-ethyl-10,10-dioctyl-5,10-dihydroindeno[1,2-b]indol-2-y1)benzo[c][1,2,5] thiadiazole] (PIIBT) and poly[4-(5-(5-ethyl-10,10-dioctyl-8-(thiophen-2-yl)-5,10-dihydroindeno[1,2-b] indol-2-yl)thiophen-2-yl)benzo[c][1,2,5]thiadiazole] (PIIDTBT). The photophysical studies of PIIBT and PIIDTBT reveal the bandgaps 1.99 and 1.75 eV, respectively. Both the polymers showing a deep-lying highest occupied molecular orbital (HOMO) energy levels similar to -5.37 eV. The hole mobilities of PIIBT (4.03 x 10(-6) cm(2)/V s) and PIIDTBT (1.94 x 10(-4) cm(2)/V s) were studied by the space charge limited current (SCLC) method. Owing to the incorporation of the thiophene moiety as a pi-spacer, PIIDTBT displayed extended pi-electron conjugation and improved intermolecular pi pi interaction in the polymer backbone. The bulk heterojunction polymer solar cells (BHJ PSCs) fabricated using PIIBT:PC71BM (1:3, 1.5 wt%) exhibited a power conversion efficiency (PCE) of 1.23%, which was enhanced to 3.72% for the BHJ PSCs based on PIIDTBT:PCTIBM (1:3, 1.5 wt%) blend. The high hole mobility of PIIDTBT is in good agreement with its high short-circuit current density (J(sc)) and fill factor (FF). This is the first report of an enhanced PCE using indeno[1,2-b]indole derivative as a donor material in BHJ PSCs. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.polymer.2013.07.004
• 作为产物：
  描述：

  1-茚酮 在 盐酸 、 四(三苯基膦)钯 、 溴 、 sodium hydride 、 溶剂黄146 、 sodium t-butanolate 作用下， 以 四氢呋喃 、 乙醇 、 氯仿 、 水 、 二甲基亚砜 、 甲苯 为溶剂， 反应 29.09h， 生成 5-ethyl-10,10-dioctyl-2,8-di(thiophen-2-yl)-5,10-dihydroindeno[1,2-b]indole
  参考文献：
  名称：

  Synthesis and characterization of new indeno[1,2-b]indole-co-benzothiadiazole-based π-conjugated ladder type polymers for bulk heterojunction polymer solar cells

  摘要：

  We have developed a new ladder type, tetrafused, pi-conjugated building block with indeno[1,2-b]indole (II) and extended the pi-conjugation of the indeno[1,2-b]indole ring by incorporating a thiophene it-spacer in the 2nd and 8th positions to attain dithiophene-substituted indeno[1,2-b]indole (IIDT). The two newly synthesized donor monomers II and IIDT were polymerized with 2,1,3-benzothiadiazole (BT) acceptor to obtain poly[4-(5-ethyl-10,10-dioctyl-5,10-dihydroindeno[1,2-b]indol-2-y1)benzo[c][1,2,5] thiadiazole] (PIIBT) and poly[4-(5-(5-ethyl-10,10-dioctyl-8-(thiophen-2-yl)-5,10-dihydroindeno[1,2-b] indol-2-yl)thiophen-2-yl)benzo[c][1,2,5]thiadiazole] (PIIDTBT). The photophysical studies of PIIBT and PIIDTBT reveal the bandgaps 1.99 and 1.75 eV, respectively. Both the polymers showing a deep-lying highest occupied molecular orbital (HOMO) energy levels similar to -5.37 eV. The hole mobilities of PIIBT (4.03 x 10(-6) cm(2)/V s) and PIIDTBT (1.94 x 10(-4) cm(2)/V s) were studied by the space charge limited current (SCLC) method. Owing to the incorporation of the thiophene moiety as a pi-spacer, PIIDTBT displayed extended pi-electron conjugation and improved intermolecular pi pi interaction in the polymer backbone. The bulk heterojunction polymer solar cells (BHJ PSCs) fabricated using PIIBT:PC71BM (1:3, 1.5 wt%) exhibited a power conversion efficiency (PCE) of 1.23%, which was enhanced to 3.72% for the BHJ PSCs based on PIIDTBT:PCTIBM (1:3, 1.5 wt%) blend. The high hole mobility of PIIDTBT is in good agreement with its high short-circuit current density (J(sc)) and fill factor (FF). This is the first report of an enhanced PCE using indeno[1,2-b]indole derivative as a donor material in BHJ PSCs. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.polymer.2013.07.004