N,N'-dihydroxythieno[3,2-g][1]benzothiophene-4,5-diimine | 1415761-29-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: N,N'-dihydroxythieno[3,2-g][1]benzothiophene-4,5-diimine
• 英文别名: benzo[1,2-b:6,5-b']dithiophene-4,5-dione dioxime
• CAS: 1415761-29-3
• 化学式: C₁₀H₆N₂O₂S₂
• 分子量: 250.302
• InChiKey: RPGPNESMAKLIJJ-UHFFFAOYSA-N

物化性质

• 沸点：
  589.9±48.0 °C(Predicted)
• 密度：
  1.77±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.85
• 重原子数：
  16.0
• 可旋转键数：
  0.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  65.18
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  N,N'-dihydroxythieno[3,2-g][1]benzothiophene-4,5-diimine 在 二氯化二硫 、 palladium 10% on activated carbon 、 溴 、 一水合肼 作用下， 以 乙醇 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 63.0h， 生成 5,8-二溴二噻吩并[3',2':3,4;2'',3'':5,6]苯并[1,2-c][1,2,5]噻二唑
  参考文献：
  名称：

  Efficient Synthesis of Benzo[1,2-b:6,5-b′]dithiophene-4,5-dione (BDTD) and Its Chemical Transformations into Precursors for π-Conjugated Materials

  摘要：

  A straightforward synthesis of the fused-aromatic dione benzo[1,2-b:6,5-b']dithiophene-4,5-dione (BDTD) has been developed. This fused-aromatic dione was subjected to various chemical transformations to generate diverse molecules with potential use in pi-conjugated materials for organic electronics.

  DOI：

  10.1021/ol302704v
• 作为产物：
  描述：

  2,7-bis(trimethylsilyl)benzo[1,2-b:6,5-b']dithiophene-4,5-dione 在 硫酸 、 盐酸羟胺 作用下， 以 乙醇 为溶剂， 反应 24.0h， 生成 N,N'-dihydroxythieno[3,2-g][1]benzothiophene-4,5-diimine
  参考文献：
  名称：

  Efficient Synthesis of Benzo[1,2-b:6,5-b′]dithiophene-4,5-dione (BDTD) and Its Chemical Transformations into Precursors for π-Conjugated Materials

  摘要：

  A straightforward synthesis of the fused-aromatic dione benzo[1,2-b:6,5-b']dithiophene-4,5-dione (BDTD) has been developed. This fused-aromatic dione was subjected to various chemical transformations to generate diverse molecules with potential use in pi-conjugated materials for organic electronics.

  DOI：

  10.1021/ol302704v

文献信息

• Synthesis, optical properties and charge transport characteristics of a series of novel thiophene-fused phenazine derivatives
  作者：Yongfa Xie、Takuya Fujimoto、Simon Dalgleish、Yoshiaki Shuku、Michio M. Matsushita、Kunio Awaga

  DOI：10.1039/c3tc30346b

  日期：——

  synthesized via a simple condensation reaction between diketones and diamines. The redox potentials, UV-vis absorption spectra and fluorescence spectra of these derivatives are significantly affected by the positions of the sulfur atoms and the alkyl groups. The observed electronic properties were well reproduced by theoretical calculations based on density functional theory. X-ray analyses of these derivatives

  通过合成了一系列的四噻吩吩嗪衍生物（t- TTP，1- TTP，m -TTP及其烷基取代衍生物）。二酮和二胺之间的简单缩合反应。这些衍生物的氧化还原电势，紫外可见吸收光谱和荧光光谱受硫原子和烷基位置的影响很大。通过基于密度泛函理论的理论计算可以很好地再现观察到的电子性能。对这些导数的X射线分析揭示了广泛的π-π相互作用和短暂的S⋯S接触。烷基取代的衍生物通过气相沉积提供高度结晶的薄膜，并显示出合理的场效应晶体管性能。还研究了这些材料的掺杂单晶的电导率，并显示出在I 2上增加了几个数量级。蒸气掺杂。这些晶体的π-π堆叠结构和导电性能表明，这些噻吩稠合的吩嗪是用于有机电子产品的有用材料。
• New Quinoxaline-Containing Monomers for Narrow-Bandgap Polymers
  作者：M. L. Keshtov、S. A. Kuklin、I. O. Konstantinov、D. Yu. Godovskii、Y. Zou、I. E. Ostapov、E. E. Makhaeva、A. R. Khokhlov

  DOI：10.1134/s001250081809001x

  日期：2018.9

  Two new fused quinoxaline-containing monomers-2,3-bis(9-(2-decyltetradecyl)-9H-carbazol-3-yl)dithieno[3,2-f:2'3'-h]quinoxaline (M1) and 2,5-di(nonadecan-3-yl)bis[1,3]thiazolo[4,5-a:5',4'-c]bisthieno[3,2-h:2',3'-j]phenazine (M2)-have been synthesized in high yields of 88 and 83% as promising building blocks of D-A polymers for photovoltaic applications. The optical bandgaps, found from the absorption edge, are 2.79 and 2.88 eV, respectively. The HOMO/LUMO energies of M1 and M2 are -5.83/-2.96 and -5.83/-2.98 eV, respectively. Both monomers have low-lying HOMO levels, which is favorable for a high open-circuit voltage and a high stability in air in the development of PSCs. The E-g(ec) values of monomers M1 and M2 are 2.87 and 2.85 eV and are consistent well with the optical bandgap (2.79 and 2.88 eV, respectively).
• A Family of Donor–Acceptor Photovoltaic Polymers with Fused 4,7-Dithienyl-2,1,3-benzothiadiazole Units: Effect of Structural Fusion and Side Chains
  作者：Chong-Yu Mei、Long Liang、Fu-Gang Zhao、Jin-Tu Wang、Lin-Feng Yu、Yu-Xue Li、Wei-Shi Li

  DOI：10.1021/ma401298g

  日期：2013.10.8

  A new optoelectronic building block, dithieno[3',2':3,4;2 '',3 '':5,6]benzo[1,2-c][1,2,5]thiadiazole, was designed by applying a fusion strategy on 4,7-dithienyl-2,1,3-benzothiadazole (DTBT) and named as fDTBT. In combination with benzo[1,2-b:4,5-b']dithiophene (BDT), fDTBT was used for the construction of a family of donor-acceptor copolymers, P(BDTn-fDTBT), with different side chains (n is carbon number of the side chain and varies from 8, 10, 12, 16, 20, to 24). It was found that the side chains have great impact on processing and photovoltaic properties of the polymers. P(BDTn-fDTBT) (n = 8, 10, and 12) bearing small alkyl side chains show poor solubility even in hot solvents. P(BDTn-fDTBT) (n = 20 and 24) have good solubility but inferior photovoltaic performance with an efficiency of 1.04% and 0.49%, respectively. Only P(BDT16-fDTBT) having 2-hexyldecyl side chain possesses both suitable solution processability and good photovoltaic properties with an efficiency around 4.36%. The comparison between P(BDT16-fDTBT) with the nonfused reference polymer P(BDT20-DTBT) reveals that the structural fusion on DTBT endows the polymer a deeper HOMO energy level and a better film morphology when blending with [6,6]-phenyl-C-61-butyric acid methyl ester (PC61BM), finally resulting in improved photovoltaic performance.
• Dithienoquinoxalineimide‐Based Polymer Donor Enables All‐Polymer Solar Cells Over 19 % Efficiency
  作者：Zongtao Wang、Xin Wang、Lijun Tu、Hao Wang、Mengzhen Du、Tingting Dai、Qiang Guo、Yongqiang Shi、Erjun Zhou

  DOI：10.1002/anie.202319755

  日期：2024.5.21

  All‐polymer solar cells (all‐PSCs) have been regarded as one of the most promising candidates for commercial applications owing to their outstanding advantages such as mechanical flexibility, light weight and stable film morphology. However, compared to large amount of new‐emerging excellent polymer acceptors, the development of high‐performance polymer donor lags behind. Herein, a new D‐π‐A type polymer donor, namely QQ1, was developed based on dithienoquinoxalineimide (DTQI) as the A unit, benzodithiophene with thiophene‐conjugated side chains (BDTT) as the D unit, and alkyl‐thiophene as the π‐bridge, respectively. QQ1 not only possesses a strong dipole moment, but also shows a wide band gap of 1.80 eV and a deep HOMO energy level of −5.47 eV, even without halogen substituents that are commonly indispensable for high‐performance polymer donors. When blended with a classic polymer acceptor PY‐IT, the QQ1‐based all‐PSC delivers an outstanding PCE of 18.81 %. After the introduction of F‐BTA3 as the third component, a record PCE of 19.20 % was obtained, the highest value reported so far for all‐PSCs. The impressive photovoltaic performance originates from broad absorption range, reduced energy loss, and compact π–π stacking. These results provide new insight in the rational design of novel nonhalogenated polymer donors for further development of all‐PSCs.