2-bromo-9-dodecylcarbazole | 1482521-70-9

• 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: 2-bromo-9-dodecylcarbazole
• 英文别名: 2-bromo-9-dodecyl-9H-carbazole
• CAS: 1482521-70-9
• 化学式: C₂₄H₃₂BrN
• 分子量: 414.429
• InChiKey: IAPKBTSOXNDVJS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.48
• 重原子数：
  26.0
• 可旋转键数：
  11.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  4.93
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  2-bromo-9-dodecylcarbazole 在 正丁基锂 、 potassium tert-butylate 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 18.0h， 生成 9,10-bis(N-dodecylcarbazol-2-ylvinyl-2)anthracene
  参考文献：
  名称：

  Synthesis and piezochromic luminescence of aggregation-enhanced emission 9,10-bis(N-alkylcarbazol-2-yl-vinyl-2)anthracenes

  摘要：

  Aggregation-enhanced emission active 9,10-bis(N-alkylcarbazol-2-yl-vinyl-2)anthracenes with changed length of N-alkyl chains (methyl, propyl, pentyl, and dodecyl) have been synthesized and their piezofluorochromic properties investigated. The results show that these homologues all exhibit remarkable piezofluorochromism with the pressing-induced spectral shifts of 36-45 nm, but the alkyl lengths do not affect significantly the fluorescence properties. The fluorescence emission changes induced by pressing can be restored by heat-annealing or solvent-fuming and regenerated by repressing. Powder wide-angle X-ray diffraction and differential scanning calorimetric experiments reveal that the transformation between crystalline and amorphous states upon external stimuli is responsible for piezofluorochromic behavior. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2013.07.012
• 作为产物：
  描述：

  2-溴咔唑 、 溴代十二烷 在 sodium hydroxide 作用下， 以 水 、 二甲基亚砜 为溶剂， 以75%的产率得到2-bromo-9-dodecylcarbazole
  参考文献：
  名称：

  Synthesis and piezochromic luminescence of aggregation-enhanced emission 9,10-bis(N-alkylcarbazol-2-yl-vinyl-2)anthracenes

  摘要：

  Aggregation-enhanced emission active 9,10-bis(N-alkylcarbazol-2-yl-vinyl-2)anthracenes with changed length of N-alkyl chains (methyl, propyl, pentyl, and dodecyl) have been synthesized and their piezofluorochromic properties investigated. The results show that these homologues all exhibit remarkable piezofluorochromism with the pressing-induced spectral shifts of 36-45 nm, but the alkyl lengths do not affect significantly the fluorescence properties. The fluorescence emission changes induced by pressing can be restored by heat-annealing or solvent-fuming and regenerated by repressing. Powder wide-angle X-ray diffraction and differential scanning calorimetric experiments reveal that the transformation between crystalline and amorphous states upon external stimuli is responsible for piezofluorochromic behavior. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2013.07.012

文献信息

• Catalytic Synthesis of Conjugated Azopolymers from Aromatic Diazides
  作者：John M. Andjaba、Christopher J. Rybak、Zhiyang Wang、Jianheng Ling、Jianguo Mei、Christopher Uyeda

  DOI：10.1021/jacs.1c00447

  日期：2021.3.17

  Conjugated polymers containing main chain azoarene repeat units are synthesized by a dinickel catalyzed N=N coupling reaction of aromatic diazides. The polymerization exhibits broad substrate scope and is compatible with heterocycles commonly featured in high performance organic materials, including carbazole, thiophene, propylenedioxythiophene (ProDOT), diketopyrrolopyrrole (DPP), and isoindigo. Copolymerizations

  含有主链偶氮芳烃重复单元的共轭聚合物是通过二镍催化的芳族二叠氮化物的 N=N 偶联反应合成的。该聚合反应具有广泛的底物范围，并且与高性能有机材料中常见的杂环相容，包括咔唑、噻吩、丙烯二氧噻吩 (ProDOT)、二酮吡咯并吡咯 (DPP) 和异靛蓝。可以使用单体混合物进行共聚，并且可以使用单叠氮链终止剂来安装明确定义的端基。由于偶氮键的功能性，偶氮聚合物具有独特的性质。例如，氮质子化导致 LUMO 降低和红移吸收带。此外，N=N 键具有较低的 π* 水平，允许偶氮聚合物在温和条件下可逆还原。