1,3-Dibromo-2-benzothiophene-5,6-dicarbonitrile | 1374450-75-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: 1,3-Dibromo-2-benzothiophene-5,6-dicarbonitrile
• 英文别名: 1,3-dibromo-2-benzothiophene-5,6-dicarbonitrile
• CAS: 1374450-75-5
• 化学式: C₁₀H₂Br₂N₂S
• 分子量: 342.013
• InChiKey: YWCDFYDNAFNHJT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  75.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,3-Dibromo-2-benzothiophene-5,6-dicarbonitrile 、 2-dodecyl-5-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophen-2-yl)isoindoline-1,3-dione 在 palladium catalyst 作用下， 生成 1,3-Bis[5-(2-dodecyl-1,3-dioxoisoindol-5-yl)thiophen-2-yl]-2-benzothiophene-5,6-dicarbonitrile
  参考文献：
  名称：

  利用溶液处理的分子光伏技术，利用非富勒烯n型材料的空穴转移

  摘要：

  含有p型和非富勒烯n型小分子的溶液处理有机光伏器件的功率转换效率高达2.4％。n型材料BT（TTI- n 12）2的光电特性使这些器件能够显示高开路电压（> 0.85 V），并通过空穴转移以及电子转移途径产生大量的电荷载流子，这在基于富勒烯的设备中很常见。

  DOI：

  10.1002/adma.201305444
• 作为产物：
  描述：

  5,6-dicyanobenzothiophene 在 N-溴代丁二酰亚胺(NBS) 作用下， 生成 1,3-Dibromo-2-benzothiophene-5,6-dicarbonitrile
  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

• Suppressing intermolecular interactions for enhancing the performance of exciplex‐based OLEDs
  作者：Yuan‐Cheng Hu、Li‐Ming Chen、Zong‐Liang Lin、Jhih‐Wei Lee、Wei‐Chih Wei、Tzu‐Yu Ko、Chun‐Yuan Lo、Wen‐Yi Hung、Ken‐Tsung Wong

  DOI：10.1002/jccs.202200094

  日期：2022.8

  In this study, a new triazatruxene-based donor Tr-iBu bearing branched alkyl groups is reported to suppress the aggregation found in a previously reported methyl-substituted counterpart Tr-Me. The effects of a steric factor on the propensity of exciplex formation were examined by respectively mixing these triazatruxene-based donors with PO-T2T and two new acceptors PO-T2P and PO-Pyr, all bearing phosphine

  在这项研究中，据报道，一种新的基于三氮唑烯的供体Tr-iBu带有支链烷基，可抑制先前报道的甲基取代对应物Tr-Me中发现的聚集。通过分别将这些基于三氮杂芦烯的供体与PO-T2T和两种新受体PO-T2P和PO-Pyr混合来检查空间因子对激化复合物形成倾向的影响，它们都带有氧化膦作为外围基团和N-具有不同数量氮的杂芳烃核。基于侧基的空间位阻及其对应的供体和受体分子轨道排列，分析了激子形成体系的特征。其中，形成激态复合物的共混物Tr-iBu : PO-T2P和Tr-iBu : PO-Pyr被选为发光层 (EML)，以实现具有中等最大外量子效率 (EQE max ) 的OLED 器件分别为 8.27% 和 7.54%。采用 Förster 共振能量转移策略，exciplex cohost 掺杂有荧光发射器DPy2CN，以实现深红色 OLED 器件，其发射峰中心在 674 nm，同时保持 6.28%
• 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).
• Solution-Processed, Molecular Photovoltaics that Exploit Hole Transfer from Non-Fullerene, n-Type Materials
  作者：Jessica D. Douglas、Mark S. Chen、Jeremy R. Niskala、Olivia P. Lee、Alan T. Yiu、Eric P. Young、Jean M. J. Fréchet

  DOI：10.1002/adma.201305444

  日期：2014.7

  Solution‐processed organic photovoltaic devices containing p‐type and non‐fullerene n‐type small molecules obtain power conversion efficiencies as high as 2.4%. The optoelectronic properties of the n‐type material BT(TTI‐n12)2 allow these devices to display high open‐circuit voltages (>0.85 V) and generate significant charge carriers through hole transfer in addition to the electron‐transfer pathway, which is

  含有p型和非富勒烯n型小分子的溶液处理有机光伏器件的功率转换效率高达2.4％。n型材料BT（TTI- n 12）2的光电特性使这些器件能够显示高开路电压（> 0.85 V），并通过空穴转移以及电子转移途径产生大量的电荷载流子，这在基于富勒烯的设备中很常见。