1,3-dibromo-6-octyl-thieno[3,4-f ]isoindole-5-7-dione | 1364222-93-4

• 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: 1,3-dibromo-6-octyl-thieno[3,4-f ]isoindole-5-7-dione
• 英文别名: 1,3-Dibromo-6-octylthieno[3,4-f]isoindole-5,7-dione；1,3-dibromo-6-octylthieno[3,4-f]isoindole-5,7-dione
• CAS: 1364222-93-4
• 化学式: C₁₈H₁₉Br₂NO₂S
• 分子量: 473.228
• InChiKey: MJGDDPJRSTZGPE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  65.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-辛基吡咯-2,5-二酮 在 N-溴代丁二酰亚胺(NBS) 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙基膦 作用下， 生成 1,3-dibromo-6-octyl-thieno[3,4-f ]isoindole-5-7-dione
  参考文献：
  名称：

  Functionalized Isothianaphthene Monomers That Promote Quinoidal Character in Donor–Acceptor Copolymers for Organic Photovoltaics

  摘要：

  A series of low band gap isothianaphthene-based (ITN) polymers with various electron-withdrawing substituents and intrinsic quinoidal character were synthesized, characterized, and tested in organic photovoltaic (OPV) devices. The three investigated ITN cores contained either ester, imide, or nitrile functionalities and were each synthesized in only four linear steps. The relative electron-withdrawing strength of the three substituents on the ITN moiety was evaluated and correlated to the optical and electronic properties of ITN-based copolymers. The ester- and imide-containing p-type polymers reached device efficiencies as high as 3% in bulk heterojunction blends with phenyl C-61-butyric acid methyl ester (PC61BM), while the significantly electron-deficient nitrile-functionalized polymer behaved as an n-type material with an efficiency of 0.3% in bilayer devices with poly(3-(4-n-octyl)phenylthiophene) (POPT).

  DOI：

  10.1021/ma300589k

文献信息

• Benzodithiophene and Imide-Based Copolymers for Photovoltaic Applications
  作者：Wade A. Braunecker、Zbyslaw R. Owczarczyk、Andres Garcia、Nikos Kopidakis、Ross E. Larsen、Scott R. Hammond、David S. Ginley、Dana C. Olson

  DOI：10.1021/cm2038427

  日期：2012.4.10

  Conjugated alternating copolymers were designed with low optical band gaps for organic photovoltaic (OPV) applications by considering quinoid resonance stabilization. Copolymers of thienoisoindoledione (TID) and benzodithiophene (BDT) had appreciably lower band gaps (by ∼0.4 eV) than copolymers of thienopyrroledione (TPD) and BDT. In addition to intramolecular charge transfer stabilization (i.e., the

  考虑到醌型共振稳定性，共轭交替共聚物的光学带隙低，设计用于有机光伏（OPV）应用。噻吩异吲哚二酮（TID）和苯并二噻吩（BDT）的共聚物的带隙（约0.4eV）比噻吩并吡咯二酮（TPD）和BDT的共聚物低得多。除了分子内电荷转移稳定化（即“推挽”效应）外，前者共聚物的醌型共振结构还通过增加异吲哚单元中的芳香族共振能而得以稳定。另外，可以通过对BDT单体进行化学修饰来调节共聚物的HOMO含量，从而在光伏器件中产生大于1 V的开路电压。尽管优化了带隙，但含TID的聚合物仍显示出较低的光电导性，由时间分辨的微波电导率确定，与TPD类似物相比，器件效率降低（2.1％对4.8％）。这些结果部分归因于形态，因为计算模型表明TID共聚物具有扭曲的主链，并且X射线衍射数据表明聚合物膜未形成有序域，而TPD共聚物的平面性明显更高，并显示出形成了部分有序域。 。
• Functionalized Isothianaphthene Monomers That Promote Quinoidal Character in Donor–Acceptor Copolymers for Organic Photovoltaics
  作者：Jessica D. Douglas、Gianmarco Griffini、Thomas W. Holcombe、Eric P. Young、Olivia P. Lee、Mark S. Chen、Jean M. J. Fréchet

  DOI：10.1021/ma300589k

  日期：2012.5.22

  A series of low band gap isothianaphthene-based (ITN) polymers with various electron-withdrawing substituents and intrinsic quinoidal character were synthesized, characterized, and tested in organic photovoltaic (OPV) devices. The three investigated ITN cores contained either ester, imide, or nitrile functionalities and were each synthesized in only four linear steps. The relative electron-withdrawing strength of the three substituents on the ITN moiety was evaluated and correlated to the optical and electronic properties of ITN-based copolymers. The ester- and imide-containing p-type polymers reached device efficiencies as high as 3% in bulk heterojunction blends with phenyl C-61-butyric acid methyl ester (PC61BM), while the significantly electron-deficient nitrile-functionalized polymer behaved as an n-type material with an efficiency of 0.3% in bilayer devices with poly(3-(4-n-octyl)phenylthiophene) (POPT).