6-(2-ethylhexyl)-5H-thieno[3,4-f]isoindole-5,7(6H)-dione | 335594-58-6

• 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: 6-(2-ethylhexyl)-5H-thieno[3,4-f]isoindole-5,7(6H)-dione
• 英文别名: 6-(2-Ethylhexyl)-5H-thieno[3,4-f]isoindole-5,7(6H)-dione；6-(2-ethylhexyl)thieno[3,4-f]isoindole-5,7-dione
• CAS: 335594-58-6
• 化学式: C₁₈H₂₁NO₂S
• 分子量: 315.436
• InChiKey: FRJMWUCICRIVPW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  22
• 可旋转键数：
  6
• 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

• 作为反应物：
  描述：

  6-(2-ethylhexyl)-5H-thieno[3,4-f]isoindole-5,7(6H)-dione 在 N-溴代丁二酰亚胺(NBS) 作用下， 生成 1,3-Dibromo-6-(2-ethylhexyl)-5H-thieno[3,4-f]isoindole-5,7(6H)-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
• 作为产物：
  描述：

  噻吩-3,4-二甲醛 、 N-(2-乙基己基)马来酰亚胺 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙基膦 作用下， 生成 6-(2-ethylhexyl)-5H-thieno[3,4-f]isoindole-5,7(6H)-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

• Direct C-H Arylation as a Chemoselective Single-Step Access to π-Acceptor-π Type Building Blocks
  作者：Kuan-Ming Lu、Wei-Ming Li、Po-Yu Lin、Kuan-Ting Liu、Ching-Yuan Liu

  DOI：10.1002/adsc.201700762

  日期：2017.11.10

  Different from the traditional multi‐step synthesis, a chemoselective direct C–H arylation is reported for the single‐step synthesis of various useful π–acceptor–π (π–A–π) type building blocks for use in organic electronics. This well‐optimized C–H heteroarylation exhibits good product yields, broad substrate scope, and high functional group compatibility. Applications in the efficient synthesis of

  与传统的多步合成方法不同，据报道，化学合成的直接C–H芳基化反应可用于有机电子中各种有用的π–受体–π（π–A–π）类型构建单元的一步合成。经过充分优化的C–H杂芳基化具有良好的产品收率，广泛的底物范围和高度的官能团相容性。还展示了在用于染料敏化太阳能电池（DSSC）的新型无金属染料敏化剂的高效合成中的应用。
• 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).