3,6-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9-(4-dodecyloxyphenyl)carbazole | 865163-48-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 3,6-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9-(4-dodecyloxyphenyl)carbazole
• 英文别名: 9-(4-Dodecoxyphenyl)-3,6-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)carbazole；9-(4-dodecoxyphenyl)-3,6-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)carbazole
• CAS: 865163-48-0
• 化学式: C₄₂H₅₉B₂NO₅
• 分子量: 679.556
• InChiKey: RHEDWTIKAQOPKN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.68
• 重原子数：
  50
• 可旋转键数：
  15
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  51.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1-十二烷氧基-4-碘苯 在 N-溴代丁二酰亚胺(NBS) 、 正丁基锂 、 铜 、 potassium carbonate 作用下， 以 四氢呋喃 、 正己烷 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 42.0h， 生成 3,6-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9-(4-dodecyloxyphenyl)carbazole
  参考文献：
  名称：

  Synthesis, Characterization, and Optical and Electrochemical Properties of New 2,1,3-Benzoselenadiazole-Based CT-Type Copolymers

  摘要：

  New alternating donor-acceptor charge-transfer (CT)-type copolymers consisting of didodecyloxy-p-phenylene (Ph), N-(4-dodecyloxyphenyl)carbazole (Cz), or N-hexyldiphenylamine (Da) unit (pi-electron donor) and 2,1,3-benzoselenadiazole (BSe) unit ( T-electron acceptor) were prepared by palladium-catalyzed Suzuki coupling reaction in 85-96% yields. The copolymers with the Ph and Cz units were soluble in common organic solvents and gave number-average molecular weights of 8300 and 6600, respectively, in GPC analysis; the copolymer with the Da unit was partly soluble in the solvents. The UV-vis absorption peak of the polymers appeared in the range of 420-530 nm in solutions and films, and the optical transition is considered to be accompanied by CT from the donor unit to the BSe unit. Quantum-chemical calculations of a trimeric model compound (Ph-BSe-Ph: 10) supported the notion that the optical activation of the copolymer involved the CT process. Cyclic voltammetry revealed that the copolymers were susceptible to both electrochemical oxidation and reduction, and they had a LUMO level ranging from -3.08 to -2.91 eV and a HOMO level ranging from -5.56 to -5.12 eV. Comparison of the electronic effect of the BSe unit with that of a 2,1,3-benzothiadiazole unit is discussed.

  DOI：

  10.1021/ma051102i

文献信息

• Synthesis, Characterization, and Optical and Electrochemical Properties of New 2,1,3-Benzoselenadiazole-Based CT-Type Copolymers
  作者：Takuma Yasuda、Tatsuya Imase、Takakazu Yamamoto

  DOI：10.1021/ma051102i

  日期：2005.8.1

  New alternating donor-acceptor charge-transfer (CT)-type copolymers consisting of didodecyloxy-p-phenylene (Ph), N-(4-dodecyloxyphenyl)carbazole (Cz), or N-hexyldiphenylamine (Da) unit (pi-electron donor) and 2,1,3-benzoselenadiazole (BSe) unit ( T-electron acceptor) were prepared by palladium-catalyzed Suzuki coupling reaction in 85-96% yields. The copolymers with the Ph and Cz units were soluble in common organic solvents and gave number-average molecular weights of 8300 and 6600, respectively, in GPC analysis; the copolymer with the Da unit was partly soluble in the solvents. The UV-vis absorption peak of the polymers appeared in the range of 420-530 nm in solutions and films, and the optical transition is considered to be accompanied by CT from the donor unit to the BSe unit. Quantum-chemical calculations of a trimeric model compound (Ph-BSe-Ph: 10) supported the notion that the optical activation of the copolymer involved the CT process. Cyclic voltammetry revealed that the copolymers were susceptible to both electrochemical oxidation and reduction, and they had a LUMO level ranging from -3.08 to -2.91 eV and a HOMO level ranging from -5.56 to -5.12 eV. Comparison of the electronic effect of the BSe unit with that of a 2,1,3-benzothiadiazole unit is discussed.