5-octyl-2,7-dithia-5-azacyclopenta[a]pentalene-4,6-dione | 1431850-19-9

• 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-octyl-2,7-dithia-5-azacyclopenta[a]pentalene-4,6-dione
• 英文别名: 6-octyl-5H-thieno[3',4':4,5]thieno[2,3-c]pyrrole-5,7(6H)-dione；N-octyl-2,7-dithia-5-azacyclopenta[a]pentalene-4,6-dione；10-Octyl-4,7-dithia-10-azatricyclo[6.3.0.02,6]undeca-1(8),2,5-triene-9,11-dione
• CAS: 1431850-19-9
• 化学式: C₁₆H₁₉NO₂S₂
• 分子量: 321.464
• InChiKey: WWRUYUVEYUHTHX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  93.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-octyl-2,7-dithia-5-azacyclopenta[a]pentalene-4,6-dione 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 氯仿 为溶剂， 生成 ethyl 2-(4-bromothiophen-3-yl)-2-oxoacetate
  参考文献：
  名称：

  Highly Stable Polymer Solar Cells Based on Poly(dithienobenzodithiophene-co-thienothiophene)

  摘要：

  It is important to develop new denor (D)acceptor (A) type low band gap polymers for highly stable polymer solar cells (PSCs). Here, we describe the synthesis and photovoltaic properties of two D-A type low band gap polymers. The polymers consist of dithienobentodfthiophene (DTBDT) moieties with expanded conjugation side: groups as donors and 2-ethyl-1-(thieno[3,4-b]thiophen-2yl)hwtan-1-one (TTEH) or 6-octyl-5H-thieno[3',4':4,5]thieno[2,3-c]pyrrole-5,7(6H)-dione (DTPD) as acceptors to give pDTBDT-TTEH and pDTBDT-DTPD polymers, respectively. The pDTBDT-TTEH is quite flat, resulting in a highly crystalline film. In contrast, the pDTBDT-DTPD is highly twisted to yield an amorphous film. Photovoltaic devices based on pDTBDT-TTEH and pDTBDT-DTPD exhibited power conversion efficiencies (PCEs) of 6.74% and 4.44%, respectively. The PCE difference results mainly from morphological differences between the two polymer:PC71BM blend films; the pDTBDT-TTEH polymer formed a nanoscopically networked domains in the blend state, while the pDTBDT-DTPD polymer film contained aggregated domains with large phase separation between the poly-mer and PC71BM molecules. Importantly, we observed that pDTBDT-TTEH-based devices showed excellent stability-in air, retaining 95% of the initial PCE after storage for over 1000 h without encapsulation. The high stability of the pDTBDT-TTEH-based device was originated mainly by the crystalline nature of the pDTBDT-TTEH:PC71BM film. This work suggests that designing highly conjugated planar backboned polymers is crucial to improve not only the photovoltaic performance but also the stability of PSCs.

  DOI：

  10.1021/acs.macromol.5b00514
• 作为产物：
  描述：

  thieno[3,4-b]thiophenefuran-2,3-dione 在 氯化亚砜 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 5-octyl-2,7-dithia-5-azacyclopenta[a]pentalene-4,6-dione
  参考文献：
  名称：

  N-Octyl-2,7-dithia-5-azacyclopenta[a]pentalene-4,6-dione-Based Low Band Gap Polymers for Efficient Solar Cells

  摘要：

  We report the synthesis, characterization, and solar cell 15 properties of new donor-acceptor-type low band gap polymers (POBDTPD and PEBDTPD) that incorporate dialkoxybenzodithiophene (BDT) as the g donor and N-octyl-2,7-dithia-5-azacyclopenta[a]pentalene-4,6-dione (DTPD) as the acceptor. The newly developed DTPD moiety was carefully designed to lower a band gap via strong interaction between donor acceptor moieties and keep polymer energy levels deep. Remarkably, the DTPD acceptor moiety effectively widens the light absorption range of the polymers up to similar to 900 nm while positioning their HOMO and LUMO levels in the optimal range, i.e., -5.3 3 and -4.0 eV, respectively, for high power conversion efficiencies (PCEs) as we intended. Solar cell devices were fabricated according to the structure ITO/PEDOT:PSS/photoactive (polymer:PC70BM)/TiO2/Al. The POBDTPD devices exhibited a PCE of 4.7% with a V-oc of 070 V, a J(sc) of 10.6 in mA/cm(2), and a FF of 0.64. The PEBDTPD devices yielded a higher PCE of 5.3% with a V-oc of 0.72 V, a J(sc) of 13.5 mA/cm(2), and a FF of 0.54. AFM, TEM, and PL quenching measurements revealed that the high J(sc)s are a result of the appropriate morphology and efficient charge separation. In comparing the performances of the two polymer devices, the higher J(sc) for the PEBDTPD device was attributed to its better nanoscale phase separation, smoother surface, and higher carrier mobility in the polymer:PC70BM blend films. The higher FF for the POBDTPD device was ascribed to a good balance between the hole and electron mobilities. Overall, we demonstrate that the DTPD unit is a promising electron accepting moiety to develop high performance low band gap polymers.

  DOI：

  10.1021/ma400257q

文献信息

• POLYMER AND SOLAR CELL USING THE SAME
  申请人：KABUSHIKI KAISHA TOSHIBA

  公开号：US20160099414A1

  公开（公告）日：2016-04-07

  In one embodiment, a polymer includes a repeating unit represented by a formula (1) shown below. A weight-average molecular weight of the polymer is in a range of 3000 or more to 1000000 or less. R1 indicates a monovalent group selected from hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aromatic group, and a substituted or unsubstituted hetero-aromatic group. R2, R3, and R4 indicate independently a monovalent group selected from hydrogen, halogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aromatic group, and a substituted or unsubstituted hetero-aromatic group. X, Y, and Z indicate independently an atom selected from O, S, and Se.
• US9818945B2
  申请人：——

  公开号：US9818945B2

  公开（公告）日：2017-11-14
• [EN] POLYMER AND SOLAR CELL USING THE SAME<br/>[FR] POLYMÈRE ET CELLULE SOLAIRE L'UTILISANT
  申请人：TOSHIBA KK

  公开号：WO2014208011A1

  公开（公告）日：2014-12-31

  In one embodiment, a polymer includes a repeating unit represented by a formula (1) shown below. A weight-average molecular weight of the polymer is in a range of 3000 or more to 1000000 or less. R1 indicates a monovalent group selected from hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aromatic group, and a substituted or unsubstituted hetero-aromatic group. R2, R3, and R4 indicate independently a monovalent group selected from hydrogen, halogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aromatic group, and a substituted or unsubstituted hetero-aromatic group. X, Y, and Z indicate independently an atom selected from O, S, and Se.