2-(heptadecan-9-yl)isoindoline-1,3-dione | 943920-62-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 2-(heptadecan-9-yl)isoindoline-1,3-dione
• 英文别名: N-(heptadecan-9-yl)phthalimide
• CAS: 943920-62-5
• 化学式: C₂₅H₃₉NO₂
• 分子量: 385.59
• InChiKey: CWJNPJJCDDIFNQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.15
• 重原子数：
  28.0
• 可旋转键数：
  15.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  37.38
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2-(heptadecan-9-yl)isoindoline-1,3-dione 在 C.I.酸性橙108 、 溶剂黄146 作用下， 反应 3.0h， 生成 N-(1-Octyl-nonyl)-3,6-dibromo-phthalimide
  参考文献：
  名称：

  Multifunctional materials for OFETs, LEFETs and NIR PLEDs

  摘要：

  邻苯二甲酰亚胺-噻吩共聚物是多功能材料，具有相当高的光致发光效率、双极性迁移率，并且在单层近红外发射有机发光二极管中表现非常出色作为宿主材料。

  DOI：

  10.1039/c4tc00342j
• 作为产物：
  描述：

  正辛基镁溴盐 在 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 生成 2-(heptadecan-9-yl)isoindoline-1,3-dione
  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

• 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。