4-[3,6-Bis(4-carbazol-9-ylphenoxy)carbazol-9-yl]phenol | 1352916-26-7

• 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: 4-[3,6-Bis(4-carbazol-9-ylphenoxy)carbazol-9-yl]phenol
• 英文别名: 4-[3,6-bis(4-carbazol-9-ylphenoxy)carbazol-9-yl]phenol
• CAS: 1352916-26-7
• 化学式: C₅₄H₃₅N₃O₃
• 分子量: 773.89
• InChiKey: SUOPFJQVBGZVSO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.8
• 重原子数：
  60
• 可旋转键数：
  7
• 环数：
  12.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  53.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-[3,6-Bis(4-carbazol-9-ylphenoxy)carbazol-9-yl]phenol 、 三(4-溴苯基)胺 在 copper(l) iodide 、 N,N-二甲基甘氨酸盐酸盐 、 caesium carbonate 作用下， 以 苯甲腈 为溶剂， 反应 4.0h， 以31%的产率得到tris(4-(4-(3,6-bis(4-(9H-carbazol-9-yl)phenoxy)-9H-carbazol-9-yl)phenoxy)phenyl)amine
  参考文献：
  名称：

  Synthesis and Properties of Oxygen-Linked N-Phenylcarbazole Dendrimers

  摘要：

  A series of novel oxygen-linked N-phenylcarbazole (NPC) dendritic wedges (3-5) and triphenyl-amine-centered dendrimers (CBD-G0 to -G2) have been synthesized and extensively studied. The aryl-oxygen-aryl (Ar-O-Ar) linkages were established on 3,6-positions of carbazole and 4-position of N-phenyl group. UV-vis spectra revealed that the Ar-O-Ar linkage would break down the pi conjugation and make NPC units manifest their individual absorption moiety. Both steady-state luminescence and fluorescence decay dynamics at room temperature and 77 K in tetrahydrofuran suggested that the transfer of energy from the carbazole wedges to the triphenylamine (TPA) core operates in CBD-G1, so that the luminescence mainly arises from the core unit. The quenching of the emission from carbazole wedges by the TPA core becomes less effective as the generation develops into CBD-G2. The oxidation potential of the NPC derivatives clearly revealed the mesomeric electron-donating effect of the oxygen atom and inductive electron-withdrawing effect of the carbazole unit. The potential gradient could be established on those triphenylamine-centered dendrimers (CBD-G1 and CBD-G2), such that the outer layer is electron-poor and the inner layer is electron-rich. It is remarkable that the HOMO level of the NPC dendrimers is as high as -5.17 eV and triplet energy level is kept above 2.85 eV. These levels of HOMO and triplet energy, together with good thermal stability and compatibility of solution processing, make NPC dendrimers ideal host materials for blue triplet emitters. Using CBD-G2 as the host material, the FIrpic-doped solution-processed light-emitting diodes were fabricated, and maximum luminous efficiency could be achieved at a record high of 24.7 cd/A at 484 cd/m(2).

  DOI：

  10.1021/ma202433y
• 作为产物：
  描述：

  在 吡啶盐酸盐 作用下， 以 N-甲基吡咯烷酮 为溶剂， 反应 7.0h， 以86%的产率得到4-[3,6-Bis(4-carbazol-9-ylphenoxy)carbazol-9-yl]phenol
  参考文献：
  名称：

  Synthesis and Properties of Oxygen-Linked N-Phenylcarbazole Dendrimers

  摘要：

  A series of novel oxygen-linked N-phenylcarbazole (NPC) dendritic wedges (3-5) and triphenyl-amine-centered dendrimers (CBD-G0 to -G2) have been synthesized and extensively studied. The aryl-oxygen-aryl (Ar-O-Ar) linkages were established on 3,6-positions of carbazole and 4-position of N-phenyl group. UV-vis spectra revealed that the Ar-O-Ar linkage would break down the pi conjugation and make NPC units manifest their individual absorption moiety. Both steady-state luminescence and fluorescence decay dynamics at room temperature and 77 K in tetrahydrofuran suggested that the transfer of energy from the carbazole wedges to the triphenylamine (TPA) core operates in CBD-G1, so that the luminescence mainly arises from the core unit. The quenching of the emission from carbazole wedges by the TPA core becomes less effective as the generation develops into CBD-G2. The oxidation potential of the NPC derivatives clearly revealed the mesomeric electron-donating effect of the oxygen atom and inductive electron-withdrawing effect of the carbazole unit. The potential gradient could be established on those triphenylamine-centered dendrimers (CBD-G1 and CBD-G2), such that the outer layer is electron-poor and the inner layer is electron-rich. It is remarkable that the HOMO level of the NPC dendrimers is as high as -5.17 eV and triplet energy level is kept above 2.85 eV. These levels of HOMO and triplet energy, together with good thermal stability and compatibility of solution processing, make NPC dendrimers ideal host materials for blue triplet emitters. Using CBD-G2 as the host material, the FIrpic-doped solution-processed light-emitting diodes were fabricated, and maximum luminous efficiency could be achieved at a record high of 24.7 cd/A at 484 cd/m(2).

  DOI：

  10.1021/ma202433y

文献信息

• Synthesis and Properties of Oxygen-Linked <i>N</i>-Phenylcarbazole Dendrimers
  作者：Chung-Chieh Lee、Man-kit Leung、Pei-Yu Lee、Tien-Lung Chiu、Jiun-Haw Lee、Chun Liu、Pi-Tai Chou

  DOI：10.1021/ma202433y

  日期：2012.1.24

  A series of novel oxygen-linked N-phenylcarbazole (NPC) dendritic wedges (3-5) and triphenyl-amine-centered dendrimers (CBD-G0 to -G2) have been synthesized and extensively studied. The aryl-oxygen-aryl (Ar-O-Ar) linkages were established on 3,6-positions of carbazole and 4-position of N-phenyl group. UV-vis spectra revealed that the Ar-O-Ar linkage would break down the pi conjugation and make NPC units manifest their individual absorption moiety. Both steady-state luminescence and fluorescence decay dynamics at room temperature and 77 K in tetrahydrofuran suggested that the transfer of energy from the carbazole wedges to the triphenylamine (TPA) core operates in CBD-G1, so that the luminescence mainly arises from the core unit. The quenching of the emission from carbazole wedges by the TPA core becomes less effective as the generation develops into CBD-G2. The oxidation potential of the NPC derivatives clearly revealed the mesomeric electron-donating effect of the oxygen atom and inductive electron-withdrawing effect of the carbazole unit. The potential gradient could be established on those triphenylamine-centered dendrimers (CBD-G1 and CBD-G2), such that the outer layer is electron-poor and the inner layer is electron-rich. It is remarkable that the HOMO level of the NPC dendrimers is as high as -5.17 eV and triplet energy level is kept above 2.85 eV. These levels of HOMO and triplet energy, together with good thermal stability and compatibility of solution processing, make NPC dendrimers ideal host materials for blue triplet emitters. Using CBD-G2 as the host material, the FIrpic-doped solution-processed light-emitting diodes were fabricated, and maximum luminous efficiency could be achieved at a record high of 24.7 cd/A at 484 cd/m(2).