9-(naphthalen-1-yl)-9H-carbazole-3,6-dicarbaldehyde | 885476-53-9

• 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: 9-(naphthalen-1-yl)-9H-carbazole-3,6-dicarbaldehyde
• 英文别名: 9-Naphthalen-1-ylcarbazole-3,6-dicarbaldehyde；9-naphthalen-1-ylcarbazole-3,6-dicarbaldehyde
• CAS: 885476-53-9
• 化学式: C₂₄H₁₅NO₂
• 分子量: 349.389
• InChiKey: MRBCFCLYAPSVQW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  39.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  9-(naphthalen-1-yl)-9H-carbazole-3,6-dicarbaldehyde 、 丙二腈 在 aluminum oxide 作用下， 以 甲苯 为溶剂， 反应 6.0h， 以80%的产率得到2,2'-((9-(naphthalen-1-yl)-9H-carbazol-3,3'-yl)methylene)malononitrile
  参考文献：
  名称：

  Photophysical Study of Blue, Green, and Orange-Red Light-Emitting Carbazoles

  摘要：

  Simple synthetic procedures have been developed to prepare suitably substituted stable carbazoles B1-B3, G1-G3, and R1-R3. These compounds emit blue, green, and orange-red light, respectively, and show a red-shifted emission in the solid state relative to that in solution. The extent of the shift is highly dependent on the nature and the positions of the substituents. A red-shift as high as 120 nm can be achieved by a suitable substitution, especially by N-substitution of carbazole. The presence of a carbaldehyde or malononitrile group on the carbazole moiety is found to quench fluorescence severely in solution and in the solid state, as indicated by low fluorescence quantum yields of B1 (phi(F) similar to 0.03), B3 (phi(F) similar to 0.04), and G1-G3 (phi(F) similar to 0.04-0.15). However, the effect is not the same for the fluorescence lifetime (tau(F) similar to 1-5.69 ns). The rate constants of radiative and nonradiative deactivation of B1-R3 have been found to be in the range of 6.40 x 10(6) to 9.50 x 10(8) and 1.38 x 10(8) to 9.84 x 10(8), respectively. Lowering the temperature from 25 to -10 degrees C causes a small but distinct red-shift in the emissions and a systematic increase in the phi(F) values of the blue and green emitters. Solvatochromism and concentration-dependent emissions of the compounds are also discussed.

  DOI：

  10.1021/jo9002757
• 作为产物：
  描述：

  3,6-二溴-N-(1-萘基)咔唑 、 N,N-二甲基甲酰胺 在 叔丁基锂 、 盐酸 、 水 作用下， 以 四氢呋喃 、 正戊烷 为溶剂， 反应 2.0h， 以30%的产率得到3-formyl-9-(α-naphthyl)carbazole
  参考文献：
  名称：

  Photophysical Study of Blue, Green, and Orange-Red Light-Emitting Carbazoles

  摘要：

  Simple synthetic procedures have been developed to prepare suitably substituted stable carbazoles B1-B3, G1-G3, and R1-R3. These compounds emit blue, green, and orange-red light, respectively, and show a red-shifted emission in the solid state relative to that in solution. The extent of the shift is highly dependent on the nature and the positions of the substituents. A red-shift as high as 120 nm can be achieved by a suitable substitution, especially by N-substitution of carbazole. The presence of a carbaldehyde or malononitrile group on the carbazole moiety is found to quench fluorescence severely in solution and in the solid state, as indicated by low fluorescence quantum yields of B1 (phi(F) similar to 0.03), B3 (phi(F) similar to 0.04), and G1-G3 (phi(F) similar to 0.04-0.15). However, the effect is not the same for the fluorescence lifetime (tau(F) similar to 1-5.69 ns). The rate constants of radiative and nonradiative deactivation of B1-R3 have been found to be in the range of 6.40 x 10(6) to 9.50 x 10(8) and 1.38 x 10(8) to 9.84 x 10(8), respectively. Lowering the temperature from 25 to -10 degrees C causes a small but distinct red-shift in the emissions and a systematic increase in the phi(F) values of the blue and green emitters. Solvatochromism and concentration-dependent emissions of the compounds are also discussed.

  DOI：

  10.1021/jo9002757

文献信息

• Photophysical Study of Blue, Green, and Orange-Red Light-Emitting Carbazoles
  作者：Ravi M. Adhikari、Douglas C. Neckers、Bipin K. Shah

  DOI：10.1021/jo9002757

  日期：2009.5.1

  Simple synthetic procedures have been developed to prepare suitably substituted stable carbazoles B1-B3, G1-G3, and R1-R3. These compounds emit blue, green, and orange-red light, respectively, and show a red-shifted emission in the solid state relative to that in solution. The extent of the shift is highly dependent on the nature and the positions of the substituents. A red-shift as high as 120 nm can be achieved by a suitable substitution, especially by N-substitution of carbazole. The presence of a carbaldehyde or malononitrile group on the carbazole moiety is found to quench fluorescence severely in solution and in the solid state, as indicated by low fluorescence quantum yields of B1 (phi(F) similar to 0.03), B3 (phi(F) similar to 0.04), and G1-G3 (phi(F) similar to 0.04-0.15). However, the effect is not the same for the fluorescence lifetime (tau(F) similar to 1-5.69 ns). The rate constants of radiative and nonradiative deactivation of B1-R3 have been found to be in the range of 6.40 x 10(6) to 9.50 x 10(8) and 1.38 x 10(8) to 9.84 x 10(8), respectively. Lowering the temperature from 25 to -10 degrees C causes a small but distinct red-shift in the emissions and a systematic increase in the phi(F) values of the blue and green emitters. Solvatochromism and concentration-dependent emissions of the compounds are also discussed.