2-(4-hexyl-5-(3-hexyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-2-yl)thiophen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane | 1244994-65-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 双噻吩和低聚噻吩
• 英文名称: 2-(4-hexyl-5-(3-hexyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-2-yl)thiophen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• 英文别名: 3,3'-dihexyl-5,5'-di(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,2'-bithiophene；2,2'-(3,3'-Dihexyl-2,2'-bithiophene-5,5'-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)；2-[4-hexyl-5-[3-hexyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophen-2-yl]thiophen-2-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS: 1244994-65-7
• 化学式: C₃₂H₅₂B₂O₄S₂
• 分子量: 586.516
• InChiKey: JYSRLZFQUWTGNH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.32
• 重原子数：
  40
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  93.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-溴-3-己基噻吩 在 正丁基锂 、 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) 、 magnesium 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 6.5h， 生成 2-(4-hexyl-5-(3-hexyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-2-yl)thiophen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
  参考文献：
  名称：

  Synthesis of a New Conjugated Polymer Composed of Pyrene and Bithiophene Units for Organic Solar Cells

  摘要：

  一种由芘和双噻吩单元组成的交替共轭共聚合物聚(DHBT-alt-PYR)已被合成。合成的聚合物展现出良好的溶液加工性和热稳定性，在加热至约370°C时，其重量损失不到5%。该聚合物的最大吸收和峰值光致发光（PL）发射波长分别为401 nm和548 nm。通过吸收边界确定该聚合物的光学带隙能量为2.64 eV。通过循环伏安法（CV）和光学带隙，该聚合物的最高占据分子轨道（HOMO）和最低未占据分子轨道（LUMO）能级分别为−5.48 eV和−2.84 eV。采用聚(DHBT-alt-PYR)作为电子供体，C60-PCBM或C70-PCBM作为电子受体，制备了具有典型三明治结构的聚合物光伏器件，结构为ITO/PEDOT:PSS/活性层/LiF/Al。使用C70-PCBM作为受体的器件的开路电压、短路电流和填充因子分别为0.75 V、3.80 mA/cm²和0.28，器件的最大功率转换效率为0.80%。

  DOI：

  10.1166/jnn.2011.3710

文献信息

• Band structure engineering for low band gap polymers containing thienopyrazine
  作者：Chi-Yang Chao、Chung-Hsiang Chao、Lung-Pin Chen、Ying-Chieh Hung、Shiang-Tai Lin、Wei-Fang Su、Ching-Fuh Lin

  DOI：10.1039/c2jm12312f

  日期：——

  In this research, we demonstrated that the energy levels, including highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO), and the optical absorptions of low band gap conjugated copolymers, consisting of 3-hexylthiophene (3HT) as electron-donating units and 2,3-diethylthieno[3,4-b]pyrazine (ETP) as electron-accepting units, could be systematically tuned by adjusting the composition and the geometric structure of the copolymers. Four new copolymers comprising of 3HT and ETP in different molar ratios (from 1 : 1 to 4 : 1), named P1–P4, were designed and synthesized via Suzuki coupling. The positions of the hexyl side chains on 3HT were varied to adjust the co-planarity of the copolymers. The LUMO, ranging from −2.94 eV to −3.11 eV, was lowered monotonically with increasing ETP content, and the break of co-planarity along the main chain showed a trivial effect on the LUMO. By contrast, the HOMO (−4.74 eV to −4.88 eV) was controlled by both the composition and the geometric structure of the copolymer. P2, having a twisted geometric structure, possessed a lower HOMO and a larger band gap compared to the planar P3. Bimodal optical absorptions with a relatively stronger absorption at long wavelengths were observed for all polymers which are due to intramolecular charge transfer. Optical band gaps in solution, ranging from 1.27 eV to 1.76 eV, decreased with increasing ETP content in the copolymer except P2 and the trend was consistent with the HOMO–LUMO gaps. The optical absorptions and the energy levels are further confirmed by theoretical calculations. Good co-planarity was also found to benefit the electrical conductivity of p-doped thin films. Our results suggested that tuning the composition and the geometric structure would be an effective molecular design strategy toward desired band structure for low band gap conjugated polymers based on thiophene and thienopyrazine derivatives.

  在本研究中，我们展示了低带隙共轭共聚物的能级，包括最高占据分子轨道（HOMO）和最低未占据分子轨道（LUMO），以及它们的光学吸收特性，可以通过调整共聚物的组成和几何结构进行系统调节。这些共聚物由3-己基噻吩（3HT）作为给电子单元和2,3-二乙基噻吩[3,4-b]吡唑（ETP）作为受电子单元组成，设计并合成了四种不同摩尔比（从1:1到4:1）的新型共聚物，命名为P1-P4，采用铃木偶联反应合成。3HT上的己基侧链的位置有所变化，以调节共聚物的共平面性。随着ETP含量的增加，LUMO（范围从-2.94 eV到-3.11 eV）单调下降，主链的共平面性破坏对LUMO的影响微乎其微。相比之下，HOMO（-4.74 eV到-4.88 eV）则受到共聚物的组成和几何结构的共同控制。P2具有扭曲的几何结构，相较于平面结构的P3，其HOMO较低且带隙较大。所有聚合物均观察到双峰光学吸收，长波长处的吸收相对强烈，这源于分子内电荷转移。溶液中的光学带隙范围从1.27 eV到1.76 eV，随着共聚物中ETP含量的增加而减小，除了P2外，此趋势与HOMO-LUMO间隙一致。光学吸收和能级也得到了理论计算的进一步验证。良好的共平面性被发现有利于p掺杂薄膜的电导率。我们的结果表明，调节组成和几何结构将是一种有效的分子设计策略，以实现基于噻吩和噻吡唑衍生物的低带隙共轭聚合物所需的能带结构。