4,7-bis(5-formyl-3-hexylthien-2-yl)benzo-2,1,3-thiadiazole | 1246814-44-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻二唑类
• 英文名称: 4,7-bis(5-formyl-3-hexylthien-2-yl)benzo-2,1,3-thiadiazole
• 英文别名: 5,5'-(2,1,3-benzothiadiazole-4,7-diyl)bis(3-hexylthiophene-2-carbaldehyde)；4,7-Di-(3-hexyl-2-formylthiophene-5-yl)-2,1,3-benzothiadiazole；5-[4-(5-formyl-4-hexylthiophen-2-yl)-2,1,3-benzothiadiazol-7-yl]-3-hexylthiophene-2-carbaldehyde
• CAS: 1246814-44-7
• 化学式: C₂₈H₃₂N₂O₂S₃
• 分子量: 524.772
• InChiKey: RBOVEFHICYXFAR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10
• 重原子数：
  35
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  145
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4,7-bis(5-formyl-3-hexylthien-2-yl)benzo-2,1,3-thiadiazole 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成
  参考文献：
  名称：

  Benzothiadiazole-Based D−π-A−π-D Organic Dyes with Tunable Band Gap: Synthesis and Photophysical Properties

  摘要：

  A series of symmetrical D-pi-A-pi-D molecules based on benzothiadiazole and oligo(thienylenevinylene)s were facilely developed. The investigation of their photophysical and electrochemical properties demonstrated that these compounds exhibited broad absorption covering the whole visible range with appropriate energy levels for light-harvesting donors.

  DOI：

  10.1021/ol101754q
• 作为产物：
  描述：

  4,7-二溴-2,1,3-苯并噻二唑 在 四(三苯基膦)钯 、 sodium hydroxide 、 三氯氧磷 作用下， 以 四氢呋喃 、 1,2-二氯乙烷 为溶剂， 反应 12.5h， 生成 4,7-bis(5-formyl-3-hexylthien-2-yl)benzo-2,1,3-thiadiazole
  参考文献：
  名称：

  用于染料敏化太阳能电池的含苯并噻二唑的D-π-A共轭化合物：合成，性质和光伏性能

  摘要：

  通过简便的合成方法为染料敏化太阳能电池开发了两个D - π -A共轭分子BzTCA和BzTMCA。对BzTCA和BzTMCA在稀溶液和薄膜中的光物理性质的研究表明，它们的吸收表现出对太阳光谱的广泛覆盖。BzTCA和BzTMCA的吸收特征在溶液中约710 nm处开始，在固态时约800 nm处开始。最大吸收（λ最大）为既BzTCA和BzTMCA在TiO 2胶片几乎与稀溶液中的胶片相同。发现它们的HOMO和LUMO在这些染料的中心部分重叠，从而确保了供体和受体之间的明显相互作用。对由BzTCA和BzTMCA制成的染料敏化太阳能电池性能的研究表明，功率转换效率分别为6.04％和4.68％，可以与普通的敏化剂N3相媲美。BzTMCA显示出较低的入射光子-电子转化效率（IPCE）和Ĵ SC相对于值BzTCA，这是可能是由于染料再生和电子注入过程中较弱的驱动力BzTMCA。IPCE响应区域达到近800

  DOI：

  10.1002/asia.201000158

文献信息

• A novel donor–acceptor carbazole and benzothiadiazole material for deep red and infrared emitting applications
  作者：Przemyslaw Ledwon、Pawel Zassowski、Tomasz Jarosz、Mieczyslaw Lapkowski、Pawel Wagner、Vladyslav Cherpak、Pavlo Stakhira

  DOI：10.1039/c5tc04183j

  日期：——

  A novel organic material (C1) with the structure D–π–A–π–D was synthesised and characterised. Carbazole was utilised as the electron donor and benzothiadiazole as the electron acceptor unit. The electrochemical, optical and electronic properties of the synthesised compound were studied. Compound C1 exhibits absorption in the visible and ultraviolet range with a high molar absorption coefficient. A

  合成并表征了结构为D–π–A–π–D的新型有机材料（C1）。咔唑用作电子给体，苯并噻二唑用作电子受体单元。研究了合成化合物的电化学，光学和电子性质。化合物C1在可见光和紫外线范围内显示出高摩尔吸收系数的吸收。在其发射光谱中观察到强烈的溶剂变色效应。为了估计分子在不同氧化还原状态下的性质，进行了电化学和光谱电化学测量。电子顺磁共振（EPR）测量表明自由基阳离子和自由基阴离子在不同部分上的离域。电化学和光学结果的解释得到DFT计算的支持。基于C1的OLED在红色和红外光谱范围内均表现出有效的发射，量子效率为3.13％，电流效率为6.8 cd A -1。与基于其他咔唑和苯并噻二唑单元的类似设备相比，该性能要好得多。
• Synthesis and photovoltaic properties of low-bandgap 4,7-dithien-2-yl-2,1,3-benzothiadiazole-based poly(heteroarylenevinylene)s
  作者：Shanpeng Wen、Jianing Pei、Pengfei Li、Yinhua Zhou、Weidong Cheng、Qingfeng Dong、Zaifang Li、Wenjing Tian

  DOI：10.1002/pola.24704

  日期：2011.6.15

  AbstractThree novel low‐bandgap copolymers containing alkylated 4,7‐dithien‐2‐yl‐2,1,3‐benzothiadiazole (HBT) and different electron‐rich functional groups (dialkylfluorene (PFV‐HBT), dialkyloxyphenylene (PPV‐HBT) and dialkylthiophene (PTV‐HBT)) were prepared by Horner polycondensation reactions and characterized by 1H NMR, gel permeation chromatography, and elemental analysis. The alkyl side chain brings these polymeric materials good solubility in common organic solvents, which is critical for the manufacture of solar cells in a cost‐effective manner. The copolymers exhibit low optical bandgap from 1.48 to 1.83 eV. The highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) energy levels of the copolymers were measured by cyclic voltammetry. Theoretical calculations revealed that the variation laws of HOMO and the LUMO energy levels are well consistent with cyclic voltammetry measurement. The bulk heterojunction photovoltaic devices with the structure of ITO/PEDOT‐PSS/polymer:PCBM/LiF/Al were fabricated by using the three copolymers as the donor and (6,6)‐phenyl‐C61‐butyric acid methyl ester (PCBM) as the acceptor in the active layer. The device based on PTV‐HBT:PCBM (1:4 w/w) achieved a power conversion efficiency of 1.05% under the illumination of AM 1.5, 100 mW/cm2. © 2011 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2011.
• Benzothiadiazole-Based D−π-A−π-D Organic Dyes with Tunable Band Gap: Synthesis and Photophysical Properties
  作者：Jin-Liang Wang、Qi Xiao、Jian Pei

  DOI：10.1021/ol101754q

  日期：2010.9.17

  A series of symmetrical D-pi-A-pi-D molecules based on benzothiadiazole and oligo(thienylenevinylene)s were facilely developed. The investigation of their photophysical and electrochemical properties demonstrated that these compounds exhibited broad absorption covering the whole visible range with appropriate energy levels for light-harvesting donors.
• Benzothiadiazole Containing D-π-A Conjugated Compounds for Dye-Sensitized Solar Cells: Synthesis, Properties, and Photovoltaic Performances
  作者：Zheng-Ming Tang、Ting Lei、Ke-Jian Jiang、Yan-Lin Song、Jian Pei

  DOI：10.1002/asia.201000158

  日期：——

  Two D‐π‐A conjugated molecules, BzTCA and BzTMCA, were developed through facile synthetic approaches for dye‐sensitized solar cells. The investigation of the photophysical properties of BzTCA and BzTMCA both in dilute solutions and in thin films indicates that their absorption exhibits a wide coverage of the solar spectrum. The absorption features for BzTCA and BzTMCA commence at about 710 nm in solution

  通过简便的合成方法为染料敏化太阳能电池开发了两个D - π -A共轭分子BzTCA和BzTMCA。对BzTCA和BzTMCA在稀溶液和薄膜中的光物理性质的研究表明，它们的吸收表现出对太阳光谱的广泛覆盖。BzTCA和BzTMCA的吸收特征在溶液中约710 nm处开始，在固态时约800 nm处开始。最大吸收（λ最大）为既BzTCA和BzTMCA在TiO 2胶片几乎与稀溶液中的胶片相同。发现它们的HOMO和LUMO在这些染料的中心部分重叠，从而确保了供体和受体之间的明显相互作用。对由BzTCA和BzTMCA制成的染料敏化太阳能电池性能的研究表明，功率转换效率分别为6.04％和4.68％，可以与普通的敏化剂N3相媲美。BzTMCA显示出较低的入射光子-电子转化效率（IPCE）和Ĵ SC相对于值BzTCA，这是可能是由于染料再生和电子注入过程中较弱的驱动力BzTMCA。IPCE响应区域达到近800