(Z)-2,2'-(octadec-9-ene-9,10-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) | 1379672-13-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 硼酸衍生物
• 英文名称: (Z)-2,2'-(octadec-9-ene-9,10-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)
• 英文别名: (Z)-1,2-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2-dioctylethene；4,4,5,5-tetramethyl-2-[(Z)-10-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)octadec-9-en-9-yl]-1,3,2-dioxaborolane
• CAS: 1379672-13-5
• 化学式: C₃₀H₅₈B₂O₄
• 分子量: 504.41
• InChiKey: BBJGIMUITFZYOZ-QPLCGJKRSA-N

物化性质

• 沸点：
  488.6±55.0 °C(Predicted)
• 密度：
  0.92±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.05
• 重原子数：
  36
• 可旋转键数：
  16
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,2'-(2,5-dibromo-1,4-phenylene)bis(3-bromothiophene) 、 (Z)-2,2'-(octadec-9-ene-9,10-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) 在 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 48.0h， 以59%的产率得到4,5,10,11-tetraoctylanthra[1,2-b:5,6-b']dithiophene
  参考文献：
  名称：

  New Angular-Shaped and Isomerically Pure Anthradithiophene with Lateral Aliphatic Side Chains for Conjugated Polymers: Synthesis, Characterization, and Implications for Solution-Prossessed Organic Field-Effect Transistors and Photovoltaics

  摘要：

  An isomerically pure anti-anthradithiophene (aADT) arranged in an angular shape is developed. Formation of the framework of aADT incorporating four lateral alkyl substituents was accomplished by a one-pot benzannulation via multiple Suzuki coupling. This newly designed 2,8-stannylated aADT monomer was copolymerized with a ditheniodiketopyrrolopyrrole (DPP) unit and a bithiophene unit, respectively, to furnish an alternating donor-acceptor copolymer poly(anthradithiophene-alt-dithienyldiketopyrrolopyrrole) (PaADTDPP) and a thiophene-rich poly(anthradithiophene-alt-bithiophene) (PaADTT). PaADTT with crystalline nature achieved a high FET mobility of 7.9 x 10(-2) cm(-2) V-1 s(-1) with an on-off ratio of 1.1 x 10(7). The photovoltaic device based on the PaADTDPP:PC71BM (1:2.5, w/w) blend exhibited a V-oc, of 0.66 V, a J(sc) of 9.49 mA/cm(2), and a FF of 58.4%, delivering a power conversion efficiency (PCE) of 3.66%. By adding 1.5 vol % 1-chloronaphthalene (CN) as a processing additive, the PCE can be improved to 4.24%. We demonstrated that these angular-shaped and alkylated aADT-based polymers have better organic photovoltaic (OPVs) and field-effect transistor (FETs) characteristics than the linear-shaped ADT-containing polymers.

  DOI：

  10.1021/cm301176s
• 作为产物：
  描述：

  1-溴辛烷 在 四(三苯基膦)铂 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 26.0h， 生成 (Z)-2,2'-(octadec-9-ene-9,10-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)
  参考文献：
  名称：

  一种含蒽并二噻吩的有机小分子半导体材料 及其制备方法和应用

  摘要：

  本发明公开了一种含蒽并二噻吩的有机小分子半导体材料及其制备方法和应用，所述材料结构式如式Ⅰ所示，其中，A单元为缺电子性基团；R1为氢，或者是具有1‑30个碳原子的烷基，或者是所述具有1‑30个碳原子的烷基中一个或多个碳原子被卤素原子、氧原子、烯基、炔基、芳基、羟基、氨基、羰基、羧基、酯基、氰基或硝基取代形成的基团。该材料具有较好的光捕获能力，合适的电子能级，较高的电子迁移率等独特优势，作为电子受体材料应用于有机太阳电池器件中，获得良好的器件性能。

  公开号：

  CN108117563B

文献信息

• 一种含蒽并二噻吩的有机小分子半导体材料 及其制备方法和应用
  申请人：华南协同创新研究院

  公开号：CN108117563B

  公开（公告）日：2019-12-03

  本发明公开了一种含蒽并二噻吩的有机小分子半导体材料及其制备方法和应用，所述材料结构式如式Ⅰ所示，其中，A单元为缺电子性基团；R1为氢，或者是具有1‑30个碳原子的烷基，或者是所述具有1‑30个碳原子的烷基中一个或多个碳原子被卤素原子、氧原子、烯基、炔基、芳基、羟基、氨基、羰基、羧基、酯基、氰基或硝基取代形成的基团。该材料具有较好的光捕获能力，合适的电子能级，较高的电子迁移率等独特优势，作为电子受体材料应用于有机太阳电池器件中，获得良好的器件性能。
• New Angular-Shaped and Isomerically Pure Anthradithiophene with Lateral Aliphatic Side Chains for Conjugated Polymers: Synthesis, Characterization, and Implications for Solution-Prossessed Organic Field-Effect Transistors and Photovoltaics
  作者：Jhong-Sian Wu、Chung-Te Lin、Chien-Lung Wang、Yen-Ju Cheng、Chain-Shu Hsu

  DOI：10.1021/cm301176s

  日期：2012.6.26

  An isomerically pure anti-anthradithiophene (aADT) arranged in an angular shape is developed. Formation of the framework of aADT incorporating four lateral alkyl substituents was accomplished by a one-pot benzannulation via multiple Suzuki coupling. This newly designed 2,8-stannylated aADT monomer was copolymerized with a ditheniodiketopyrrolopyrrole (DPP) unit and a bithiophene unit, respectively, to furnish an alternating donor-acceptor copolymer poly(anthradithiophene-alt-dithienyldiketopyrrolopyrrole) (PaADTDPP) and a thiophene-rich poly(anthradithiophene-alt-bithiophene) (PaADTT). PaADTT with crystalline nature achieved a high FET mobility of 7.9 x 10(-2) cm(-2) V-1 s(-1) with an on-off ratio of 1.1 x 10(7). The photovoltaic device based on the PaADTDPP:PC71BM (1:2.5, w/w) blend exhibited a V-oc, of 0.66 V, a J(sc) of 9.49 mA/cm(2), and a FF of 58.4%, delivering a power conversion efficiency (PCE) of 3.66%. By adding 1.5 vol % 1-chloronaphthalene (CN) as a processing additive, the PCE can be improved to 4.24%. We demonstrated that these angular-shaped and alkylated aADT-based polymers have better organic photovoltaic (OPVs) and field-effect transistor (FETs) characteristics than the linear-shaped ADT-containing polymers.