2-methoxy-9-methyl-9H-carbazole-3-carbaldehyde | 39027-89-9

• 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-methoxy-9-methyl-9H-carbazole-3-carbaldehyde
• 英文别名: 2-Methoxy-9-methylcarbazole-3-carbaldehyde；2-methoxy-9-methylcarbazole-3-carbaldehyde
• CAS: 39027-89-9
• 化学式: C₁₅H₁₃NO₂
• 分子量: 239.274
• InChiKey: HWJGRVSYZUPLRH-UHFFFAOYSA-N

物化性质

• 沸点：
  376.5±35.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  31.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-methoxy-9-methyl-9H-carbazole-3-carbaldehyde 在 lithium chloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以42%的产率得到2-hydroxy-9-methyl-9H-carbazole-3-carbaldehyde
  参考文献：
  名称：

  基于可逆质子转移的光致变色

  摘要：

  研究了基于亚稳态光酸和酸性变色染料之间可逆质子转移的光致变色现象。亚稳态光酸在中等照射下可逆地产生大量的质子浓度，使酸性变色染料质子化并引起颜色变化。这种机理与基于光致结构变化的常规光致变色材料的机理不同。可以通过选择不同的酸性变色染料和光酸来控制颜色变化和激发波长。在溶液和聚合物基质中均证明了在阳光或不同波长的可见光下各种颜色的可逆变化。

  DOI：

  10.1016/j.jphotochem.2014.12.008
• 作为产物：
  描述：

  2-methoxy-9-methyl-9H-carbazole 、 N,N-二甲基甲酰胺 在 三氯氧磷 作用下， 反应 5.0h， 以72%的产率得到2-methoxy-9-methyl-9H-carbazole-3-carbaldehyde
  参考文献：
  名称：

  基于可逆质子转移的光致变色

  摘要：

  研究了基于亚稳态光酸和酸性变色染料之间可逆质子转移的光致变色现象。亚稳态光酸在中等照射下可逆地产生大量的质子浓度，使酸性变色染料质子化并引起颜色变化。这种机理与基于光致结构变化的常规光致变色材料的机理不同。可以通过选择不同的酸性变色染料和光酸来控制颜色变化和激发波长。在溶液和聚合物基质中均证明了在阳光或不同波长的可见光下各种颜色的可逆变化。

  DOI：

  10.1016/j.jphotochem.2014.12.008

文献信息

• Substituted 7H-pyrido[4,3-c]carbazoles with potent anti-HIV activity
  作者：Kazuma Hirata、Chihiro Ito、Hiroshi Furukawa、Masataka Itoigawa、L.Mark Cosentino、Kuo-Hsiung Lee

  DOI：10.1016/s0960-894x(98)00708-2

  日期：1999.1

  Several substituted 7H-pyrido[4,3-c]carbazoles were synthesized from the natural product mukonal and tested for inhibition of HIV replication in H9 lymphocytes. 5-Methoxy-7-methyl-7H-pyrido[4,3-c]carbazole (7) had an EC50 value of 0.0054 microgram/mL and the highest therapeutic index (TI = 503) in the series.

  从天然产物粘蛋白合成了几种取代的7H-吡啶并[4,3-c]咔唑，并测试了其在H9淋巴细胞中对HIV复制的抑制作用。5-甲氧基-7-甲基-7H-吡啶并[4,3-c]咔唑（7）的EC50值为0.0054微克/毫升，是该系列中最高的治疗指数（TI = 503）。
• Rhodanine-3-acetic acid containing D-π-A push-pull chromophores: Effect of methoxy group on the performance of dye-sensitized solar cells
  作者：Kiran Avhad、Manoj Jadhav、Dinesh Patil、Towhid H. Chowdhury、Ashraful Islam、Idriss Bedja、Nagaiyan Sekar

  DOI：10.1016/j.orgel.2018.11.041

  日期：2019.2

  julolidine and carbazole with methoxy group as an additional auxiliary donor and rhodanine-3-acetic acid as an acceptor were synthesized, and used in dye-sensitized solar cells application. The impact of the different donors with additional methoxy group on the photophysical, electrochemical, and photovoltaic properties are studied. The electron transfer kinetics are investigated by transient absorption spectroscopy

  合成了三种有机光敏剂（TPA-R9，J-R9，CAR-R9），它们由三苯胺，甲氧吡啶和带有甲氧基的咔唑作为辅助辅助供体，并由若丹宁-3-乙酸作为受体，并用于染料敏化太阳能电池的应用。研究了具有不同甲氧基的不同供体对光物理，电化学和光伏性质的影响。通过瞬态吸收光谱和阻抗光谱研究电子转移动力学。在固定的V OC时，电子寿命按供体的顺序增加：聚氯丁二烯<二苯胺<咔唑，其顺序与V OC的增加顺序一致。在电解质存在下，瞬态吸收衰减显示CAR-R9，TPA-R9和J-R9的半衰期（τ1 /2）分别为1.40、1.98和3.81μs 。所观察到的短寿命CAR-R9由我证明最高染料再生-允许的11.29毫安厘米最高短路光电流密度-2。在不添加TBP的情况下获得的敏化剂的效率为3.01至5.40％。的CAR-R9与短路光电流密度（表现出优异的发电性能的Jsc的11.29毫安厘米）-2，开路光电压（开路电压）为0
• Reverse photochromic compound
  申请人：FUJIFILM Wako Pure Chemical Corporation

  公开号：US10696898B2

  公开（公告）日：2020-06-30

  A reverse photochromic compound of the related art has difficulty in sensing light with a wavelength of 600 nm or greater in a visible light region which has been used for medical applications. Therefore, an object of the present invention is to provide a reverse photochromic compound and a polymer which have a high sensitivity to light having a wavelength of 600 nm or greater. The present invention relates to a compound and the like represented by the following general formula (1). In the formula, R1 and R4 each independently represent a hydrogen atom or the like, R2, R3, and R5 each independently represent an alkyl group or the like, R6 represents a group having a polymerizable unsaturated group, a carboxy group, or an alkoxycarbonyl group, R31 and R32 each independently represent an alkoxy group or the like, R33 and R34 each independently represent a hydrogen atom or the like, Y1 represents an oxygen atom or a sulfur atom, An− represents an anion, n1 to n3 represent a specific integer, and R1 and R2, R3 and R4, and/or R33 and R34 may form an alkylene group.

  相关技术中的一种反向光致变色化合物难以感应波长为 600 nm 或更长的可见光区域的光，而这种光一直被用于医疗用途。因此，本发明的目的是提供一种反向光致变色化合物和聚合物，它们对波长为 600 nm 或更大的光具有高灵敏度。本发明涉及由以下通式（1）表示的化合物及类似物。 式中，R1 和 R4 各自独立地代表氢原子或类似物，R2、R3 和 R5 各自独立地代表烷基或类似物，R6 代表具有可聚合的不饱和基团、羧基或烷氧基羰基的基团、R31 和 R32 各自独立地代表烷氧基或类似基团，R33 和 R34 各自独立地代表氢原子或类似基团，Y1 代表氧原子或硫原子，An- 代表阴离子，n1 至 n3 代表特定整数，R1 和 R2、R3 和 R4 和/或 R33 和 R34 可形成亚烷基。
• Aggregation induced emissive carbazole-based push pull NLOphores: Synthesis, photophysical properties and DFT studies
  作者：Sandip K. Lanke、Nagaiyan Sekar

  DOI：10.1016/j.dyepig.2015.09.013

  日期：2016.1

  2-Alkoxy-9-methyl-9H-carbazole-3-carbaldehyde based push pull chromophore were efficiently synthesized by a multi-step reaction starting from 9H-carbazole-2-ol. The fluorescence properties of these D-pi-A chromophores were investigated in various solvents of varying polarities and in mixed solvent solutions of DMF and H2O. They exhibited low fluorescent intensity in solution but a high fluorescent intensity in aggregate forms and in their solid state due to the promising aggregation-induced emission enhancement characteristics. These dyes were fully characterized by FT-IR, H-1 NMR and HRMS spectra. The ratio of ground to excited state dipole moment of the novel push pull chromophore were calculated by Bakhshiev and Bilot-Kawski correlations. All the four dyes show more or less twisted intramolecular charge transfer (TILT) characteristics. They show a large first hyperpolarizability value ranging from 189-721 x 10(-3) esu by theoretical method and 73-330 x 10(-30) esu by experimental method. (C) 2015 Elsevier Ltd. All rights reserved.
• Novel NLOphoric 2-methoxy carbazole-based push pull chromophores: Synthesis, photophysical properties and TD-DFT Study
  作者：Sandip K. Lanke、Nagaiyan Sekar

  DOI：10.1016/j.jphotochem.2016.01.014

  日期：2016.5

  TD-DFT computation were performed to study structural, molecular, electronic and photophysical parameters of the dyes. The four dyes are showing red shifted solid sate emission in the range of 487–593 nm. The ratio of ground to excited state dipole moment of the synthesized dyes were calculated using solvent polarity correlations and DFT method. The absorption wavelength and emission wavelength values

  含“推-拉”新颖咔唑光物理性质对染料2-甲氧基-9-甲基-9-的缩合得到ħ进行了研究-咔唑-3-甲醛3具有不同的活性亚甲基部分。这些染料已通过1 H NMR很好地表征，13C NMR和HRMS光谱。在不同极性的溶剂中研究了染料的紫外可见吸收和荧光发射光谱。进行DFT和TD-DFT计算以研究染料的结构，分子，电子和光物理参数。四种染料在487–593 nm范围内显示出红移的固态状态发射。使用溶剂极性相关性和DFT方法计算了合成染料的基态与激发态偶极矩之比。发现吸收波长和发射波长值与实验结果良好吻合。通过溶剂变色法和理论方法研究了非线性光学性质。