2,6-bis((4-hexylphenyl)ethynyl)anthracene-9,10-dione | 1284214-22-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 2,6-bis((4-hexylphenyl)ethynyl)anthracene-9,10-dione
• 英文别名: 2,6-Bis[2-(4-hexylphenyl)ethynyl]anthracene-9,10-dione；2,6-bis[2-(4-hexylphenyl)ethynyl]anthracene-9,10-dione
• CAS: 1284214-22-7
• 化学式: C₄₂H₄₀O₂
• 分子量: 576.778
• InChiKey: UKAAMTKYPBDMEQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.8
• 重原子数：
  44
• 可旋转键数：
  14
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,6-bis((4-hexylphenyl)ethynyl)anthracene-9,10-dione 、 4-己基苯乙炔 在 正丁基锂 、 盐酸 、 水 、 tin(ll) chloride 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 3.55h， 以68%的产率得到2,6,9,10-tetrakis((4-hexylphenyl)ethynyl)anthracene
  参考文献：
  名称：

  Highly Crystalline 2,6,9,10-Tetrakis((4-hexylphenyl)ethynyl)anthracene for Efficient Solution-Processed Field-effect Transistors

  摘要：

  通过Sonogashira偶联和还原反应合成了一种新的含蒽的共轭分子。1-乙炔基-4-己基苯与2,6-双((4-己基苯基)乙炔基)蒽-9,10-二酮通过还原反应偶联，生成2,6,9,10-四乙炔基(4-己基苯基)蒽。我们在有机薄膜晶体管（OTFT）和单晶场效应晶体管（SC-FET）中评估了其半导体特性。OTFT的迁移率约为0.13 $cm^2\;V^{-1}\;s^{-1}$（$I_{ON}/I_{OFF}$ > $10^6$），而SC-FET的迁移率为1.00-1.35 $cm^2\;V^{-1}\;s^{-1}$，显著高于OTFT。由于2,6,9,10-四乙炔基(4-己基苯基)蒽具有高的光致发光量子产率，我们观察到在可见光照射下（${\lambda}$ = 538 nm, 12.5 ${\mu}W/cm^2$）漏电流显著增加。

  DOI：

  10.5012/bkcs.2012.33.5.1653
• 作为产物：
  描述：

  2,6-二溴蒽醌 、 4-己基苯乙炔 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 二异丙胺 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 以74%的产率得到2,6-bis((4-hexylphenyl)ethynyl)anthracene-9,10-dione
  参考文献：
  名称：

  Highly Crystalline 2,6,9,10-Tetrakis((4-hexylphenyl)ethynyl)anthracene for Efficient Solution-Processed Field-effect Transistors

  摘要：

  通过Sonogashira偶联和还原反应合成了一种新的含蒽的共轭分子。1-乙炔基-4-己基苯与2,6-双((4-己基苯基)乙炔基)蒽-9,10-二酮通过还原反应偶联，生成2,6,9,10-四乙炔基(4-己基苯基)蒽。我们在有机薄膜晶体管（OTFT）和单晶场效应晶体管（SC-FET）中评估了其半导体特性。OTFT的迁移率约为0.13 $cm^2\;V^{-1}\;s^{-1}$（$I_{ON}/I_{OFF}$ > $10^6$），而SC-FET的迁移率为1.00-1.35 $cm^2\;V^{-1}\;s^{-1}$，显著高于OTFT。由于2,6,9,10-四乙炔基(4-己基苯基)蒽具有高的光致发光量子产率，我们观察到在可见光照射下（${\lambda}$ = 538 nm, 12.5 ${\mu}W/cm^2$）漏电流显著增加。

  DOI：

  10.5012/bkcs.2012.33.5.1653

文献信息

• Semiconducting 2,6,9,10-Tetrakis(phenylethynyl)anthracene Derivatives: Effect of Substitution Positions on Molecular Energies
  作者：Jung A Hur†、Suk Young Bae、Kyung Hwan Kim、Tae Wan Lee、Min Ju Cho、Dong Hoon Choi

  DOI：10.1021/ol200299s

  日期：2011.4.15

  10-bis(phenylethynyl)anthracene, 4, and 9,10-bis((4-hexylphenyl)ethynyl)-2,6-bis (phenyl ethynyl)anthracene, 5, have been synthesized to study their electronic and photophysical properties. It should be noted that the difference between these compounds is the substitution position of 1-ethynyl-4-hexylbenzene groups into an anthracene ring. In particular, substitution in the 9,10-positions of the anthracene ring enhanced

  2,6-双（（（4-己基苯基）乙炔基）-9,10-双（苯基乙炔基）蒽，4和9,10-双（（4-己基苯基）乙炔基）-2,6-双（苯基乙炔基）蒽5已被合成来研究其电子和光物理性质。应该注意的是，这些化合物之间的区别是1-乙炔基-4-己基苯基在蒽环中的取代位置。特别地，在蒽环的9，10位上的取代增强了J聚集的分子间相互作用。由于5具有较低的带隙能量和更紧凑的膜形态，因此在薄膜晶体管器件中它具有较高的空穴迁移率（〜0.27 cm 2 V -1 s -1）。
• 2-Hexylthieno[3,2-b]thiophene-substituted Anthracene Derivatives for Organic Field Effect Transistors and Photovoltaic Cells
  作者：So-Young Jo、Jung-A Hur、Kyung-Hwan Kim、Tae-Wan Lee、Ji-Cheol Shin、Kyung-Seok Hwang、Byung-Doo Chin、Dong-Hoon Choi

  DOI：10.5012/bkcs.2012.33.9.3061

  日期：2012.9.20

  Novel 2-hexylthieno[3,2-b]thiophene-containing conjugated molecules have been synthesized via a reduction reaction using tin chloride in an acidic medium. They exhibited good solubility in common organic solvents and good self-film and crystal-forming properties. The single-crystalline objects were fabricated by a solvent slow diffusion process and then were employed for fabricating field-effect transistors (FETs) along with thinfilm transistors (TFTs). TFTs made of 5 and 6 exhibited carrier mobility as high as 0.10-0.15 $cm^2V^-1}s^-1}$. The single-crystal-based FET made of 6 showed 0.70 $cm^2V^-1}s^-1}$ which was relatively higher than that of the 5-based FET ($\mu}=0.23cm^2V^-1}s^-1}$). In addition, we fabricated organic photovoltaic (OPV) cells with new 2-hexylthieno [3,2-b]thiophene-containing conjugated molecules and methanofullerene [6,6]-phenyl C61-butyric acid methyl ester ($PC_61}BM$) without thermal annealing. The ternary system for a bulk heterojunction (BHJ) OPV cell was elaborated using $PC_61}BM$ and two p-type conjugated molecules such as 5 and 7 for modulating the molecular energy levels. As a result, the OPV cell containing 5, 7, and $PC_61}BM$ had improved results with an open-circuit voltage of 0.90 V, a short-circuit current density of 2.83 $mA/cm^2$, and a fill factor of 0.31, offering an overall power conversion efficiency (PCE) of 0.78%, which was larger than those of the devices made of only molecule 5 ($\eta}$~0.67%) or 7 ($\eta}$~0.46%) with $PC_61}BM$ under identical weight compositions.

  合成了包含2-己基噻吩[3,2-b]噻吩的共轭分子，采用在酸性介质中使用氯化锡的还原反应。这些分子在常见有机溶剂中表现出良好的溶解性以及良好的自制膜和晶体形成特性。通过溶剂缓慢扩散过程制备了单晶物体，随后用于制造场效应晶体管（FETs）和薄膜晶体管（TFTs）。由5和6制成的TFTs展现出高达0.10-0.15 $cm^2V^-1}s^-1}$的载流子迁移率。基于6的单晶FET表现出0.70 $cm^2V^-1}s^-1}$的迁移率，相对高于基于5的FET（$\mu}=0.23cm^2V^-1}s^-1}$）。此外，我们还利用新的2-己基噻吩[3,2-b]噻吩含有的共轭分子和甲烷富勒烯[6,6]-苯基C61-丁酸甲酯（$PC_61}BM$）制造了有机光伏（OPV）电池，而无需热退火。为大块异质结（BHJ）OPV电池构建了一个三元系统，采用<※>$PC_61}BM$和两种p型共轭分子，如5和7，来调节分子能级。因此，包含5、7和$PC_61}BM$的OPV电池表现出改善的结果，开路电压为0.90 V，短路电流密度为2.83 $mA/cm^2$，填充因子为0.31，总体功率转换效率（PCE）为0.78%，高于仅由分子5（$\eta}$~0.67%）或7（$\eta}$~0.46%）与$PC_61}BM$在相同重量配比下制成的器件。
• Highly Crystalline 2,6,9,10-Tetrakis((4-hexylphenyl)ethynyl)anthracene for Efficient Solution-Processed Field-effect Transistors
  作者：Jung-A Hur、Ji-Cheol Shin、Tae-Wan Lee、Kyung-Hwan Kim、Min-Ju Cho、Dong-Hoon Choi

  DOI：10.5012/bkcs.2012.33.5.1653

  日期：2012.5.20

  A new anthracene-containing conjugated molecule was synthesized through the Sonogashira coupling and reduction reactions. 1-Ethynyl-4-hexylbenzene was coupled to 2,6-bis((4-hexylphenyl) ethynyl)anthracene-9,10-dione through a reduction reaction to generate 2,6,9,10-tetrakis((4-hexylphenyl)ethynyl) anthracene. The semiconducting properties were evaluated in an organic thin film transistor (OTFT) and a single-crystal field-effect transistor (SC-FET). The OTFT showed a mobility of around 0.13 $cm^2\;V^-1}\;s^-1}$ ($I_ON}/I_OFF}$ > $10^6$), whereas the SC-FET showed a mobility of 1.00-1.35 $cm^2\;V^-1}\;s^-1}$, which is much higher than that of the OTFT. Owing to the high photoluminescence quantum yield of 2,6,9,10-tetrakis((4-hexylphenyl)ethynyl) anthracene, we could observe a significant increase in drain current under irradiation with visible light ($\lambda}$ = 538 nm, 12.5 $\mu}W/cm^2$).

  通过Sonogashira偶联和还原反应合成了一种新的含蒽的共轭分子。1-乙炔基-4-己基苯与2,6-双((4-己基苯基)乙炔基)蒽-9,10-二酮通过还原反应偶联，生成2,6,9,10-四乙炔基(4-己基苯基)蒽。我们在有机薄膜晶体管（OTFT）和单晶场效应晶体管（SC-FET）中评估了其半导体特性。OTFT的迁移率约为0.13 $cm^2\;V^-1}\;s^-1}$（$I_ON}/I_OFF}$ > $10^6$），而SC-FET的迁移率为1.00-1.35 $cm^2\;V^-1}\;s^-1}$，显著高于OTFT。由于2,6,9,10-四乙炔基(4-己基苯基)蒽具有高的光致发光量子产率，我们观察到在可见光照射下（$\lambda}$ = 538 nm, 12.5 $\mu}W/cm^2$）漏电流显著增加。