4-（Tridecan-7-基）-4H-二硫代[3,2-b：2'，3'-d]吡咯 | 1158270-38-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并吡咯类
• 中文名称: 4-（Tridecan-7-基）-4H-二硫代[3,2-b：2'，3'-d]吡咯
• 英文名称: N-(1-hexylheptyl)dithieno[3,2-b:2',3'-d]pyrrole
• 英文别名: dithieno[3,2-b:2',3'-d]pyrrole；DTP；4-(Tridecan-7-yl)-4H-dithieno[3,2-b:2',3'-d]pyrrole；7-tridecan-7-yl-3,11-dithia-7-azatricyclo[6.3.0.02,6]undeca-1(8),2(6),4,9-tetraene
• CAS: 1158270-38-2
• 化学式: C₂₁H₃₁NS₂
• 分子量: 361.616
• InChiKey: WJUWUCXVQBXBSE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.6
• 重原子数：
  24
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  61.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-（Tridecan-7-基）-4H-二硫代[3,2-b：2'，3'-d]吡咯 在 N-溴代丁二酰亚胺(NBS) 、 四(三苯基膦)钯 、 potassium carbonate 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 3.5h， 生成 6-(4-(bis(2',4'-bis(hexyloxy)-[1,1'-biphenyl]-4-yl)amino)phenyl)-4-(tridecan-7-yl)-4H-dithieno[3,2-b:2',3'-d]pyrrole-2-carbaldehyde
  参考文献：
  名称：

  Unravelling the Potential for Dithienopyrrole Sensitizers in Dye-Sensitized Solar Cells

  摘要：

  Two D-pi-A dyes based on the dithieno[3,2-b:2',3'-d]pyrrole pi-bridge (DTP) were synthesized, characterized using UV-vis absorption spectroscopy and electrochemistry, modeled using quantum chemical calculations, and used as sensitizers in dye-sensitized solar cells (DSCs). The photoelectrochemical properties and DSC performance are thoroughly compared with their cyclopenta[1,2-b:5,4-b']dithiophene (CPDT) analogues. The use of DTP results in a small increase in the zero zero transition energy reflecting the higher lying lowest unoccupied molecular orbital that is commonly reported for DTP relative to CPDT systems. This increased optical gap manifests in slightly blue-shifted incident photon-to-collected electron conversion efficiency (IPCE) responses; however, increased open-circuit photovoltage values and improved charge-transfer kinetics relative to the CPDT systems result in comparable power conversion efficiencies. The present report highlights the potential of DTP for the development of tailored sensitizers employing stronger acceptors.

  DOI：

  10.1021/cm401144j
• 作为产物：
  描述：

  3,3'-二溴-2,2'-联噻吩 、 十三烷-7-胺 在 1,1'-双(二苯基膦)二茂铁 、 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 作用下， 以 甲苯 为溶剂， 生成 4-（Tridecan-7-基）-4H-二硫代[3,2-b：2'，3'-d]吡咯
  参考文献：
  名称：

  茚和1,2,5-噻二唑基聚（2,5-二噻吩基吡咯）衍生物的电化学合成，光学，电化学和电致变色表征†

  摘要：

  将茚和苯并噻二唑单元结合到聚（噻吩基吡咯）骨架的中心吡咯环上，它们分别表示为PDIT和PBDTA。PDIT，PBDTA及其相应的共聚物（P（DIT- co -DTP）和P（BDTA- co- DTP））是电化学合成的，并报道了它们的电致变色性能。PDIT和PBDTA膜不仅被可逆地氧化和还原，而且还伴有明显的颜色变化（黄色，绿色和蓝色）。它们相应的P（DIT- co -DTP）和P（BDTA- co -DTP）共聚物薄膜呈现多色电致变色现象。Δ Ť最大的P的（DIT-共-DTP）和P（BDTA-共-DTP）膜在离子液体溶液中分别在1314 nm和930 nm处测量为45.3％和439.5％，计算得出PBDTA和P（DIT- co -DTP）膜的η为167.8 cm 2 C -1在1070纳米和177.4厘米2 ç -1分别在1314纳米，在离子液体中的溶液。基于PDIT，PBDTA，P（DIT-

  DOI：

  10.1039/c5ra27902j

文献信息

• Novel NIR-absorbing conjugated polymers for efficient polymer solar cells: effect of alkyl chain length on device performance
  作者：Wei Yue、Yun Zhao、Shuyan Shao、Hongkun Tian、Zhiyuan Xie、Yanhou Geng、Fosong Wang

  DOI：10.1039/b818885h

  日期：——

  Three low bandgap conjugated polymers, i.e., PDTPBT-C8, PDTPBT-C6 and PDTPBT-C5, which consist of alternating N-alkyl dithieno[3,2-b:2′,3′-d]pyrrole and 2,1,3-benzothiadiazole units and carry 1-octylnonyl, 1-hexylheptyl and 1-pentylhexyl as side chains, respectively, were synthesized. These polymers show strong absorption in the wavelength range of 600–900 nm with enhanced absorption coefficient as the length of alkyl chain decreases. The film morphology of the polymers and 1-(3-methoxycarbonyl)propyl-1-phenyl-[6,6]-C-61 (PCBM) blends is also dependent on the alkyl chain length. As the length decreases, the film becomes more uniform and the domian size decreases from 400–900 nm for PDTPBT-C8 to ∼50 nm for PDTPBT-C5. Bulk heterojunction photovoltaic solar cells (PSCs) were fabricated based on the blend of the polymers and PCBM with a weight ratio of 1:3. The device performance is dramatically improved as the length of the side chain decreases, due to enhanced film absorption coefficient and improved film morphology. With the polymer PDTPBT-C5, which carries the shortest alkyl chain, power conversion efficiency (PCE) up to 2.80% has been achieved. This result indicates that optimizing the structure of the solublizing alkyl chain is also crucial for the design and synthesis of high performance PSC polymeric materials.

  合成了三种窄带隙共轭聚合物，即PDTPBT-C8，PDTPBT-C6和PDTPBT-C5，它们由交替的N-烷基二噻吩并[3,2-b:2',3'-d]吡咯和2,1,3-苯并噻二唑单元组成，并分别带有1-辛基壬基，1-己基庚基和1-戊基己基侧链。这些聚合物在600-900 nm波长范围内显示出强烈的吸收，并且随着烷基链长度的减少，吸收系数增强。聚合物和1-(3-甲氧羰基)丙基-1-苯基-[6,6]-C-61（PCBM）混合物的膜形态也取决于烷基链的长度。随着链长的减少，膜变得更加均匀，域尺寸从PDTPBT-C8的400-900 nm减小到PDTPBT-C5的约50 nm。基于聚合物和PCBM的混合物（重量比为1:3）制备了体异质结光伏太阳能电池（PSCs）。由于膜吸收系数的增强和膜形态的改善，随着侧链长度的减少，器件性能显著提高。带有最短烷基链的聚合物PDTPBT-C5，其功率转换效率（PCE）达到了2.80%。这一结果表明，优化溶解性烷基链的结构对于高性能PSCs聚合物材料的设计和合成也至关重要。