2-甲基-9,10-二(2-萘基)蒽 | 804560-00-7

• 物质功能分类: 化学试剂 - 有机试剂 - 多环化合物
• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 芳基萘木脂素
• 中文名称: 2-甲基-9,10-二(2-萘基)蒽
• 中文别名: 2-甲基-9,10-双(萘-2-基)蒽
• 英文名称: MADN
• 英文别名: 2-methyl-9,10-bis(naphthalen-2-yl)anthracene；2-Methyl-9,10-di(naphthalen-2-yl)anthracene；2-methyl-9,10-dinaphthalen-2-ylanthracene
• CAS: 804560-00-7
• 化学式: C₃₅H₂₄
• 分子量: 444.576
• InChiKey: HNWFFTUWRIGBNM-UHFFFAOYSA-N

物化性质

• 熔点：
  253-258°C
• 沸点：
  607.2±50.0 °C(Predicted)
• 密度：
  1.192±0.06 g/cm3 (20 ºC 760 Torr)
• 最大波长(λmax)：
  398nm(CHCl3)(lit.)

计算性质

• 辛醇/水分配系数(LogP)：
  10.5
• 重原子数：
  35
• 可旋转键数：
  2
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.03
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

安全信息

• WGK Germany：
  3

反应信息

• 作为反应物：
  描述：

  2-甲基-9,10-二(2-萘基)蒽 在 N-溴代丁二酰亚胺(NBS) 、 2-硝基丙烷 、 2-(4-biphenyl)-5-phenyloxazole 、 potassium tert-butylate 、 potassium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二甲基亚砜 、 苯 为溶剂， 反应 0.5h， 生成 9,10-di(2-naphthalenyl)-2-vinylanthracene
  参考文献：
  名称：

  Synthesis and characterization of highly soluble blue emitting poly(2-vinylanthracene) with 9,10-di(2-naphthalenyl) and 9,10-di(3-quinolinyl) substituents

  摘要：

  Two new blue fluorescent polymers, poly(9,10-di(2-naphthalenyl)-2-vinylanthracene) (P(2ADN)) and poly(9,10-di(3-quinolinyl)-2-vinylanthracene) (P(3ADQ)), were polymerized from free radical solution addition polymerization with M-n = 21,500 and 15,400, respectively. The polymers are highly soluble in common organic solvents while P(3ADQ) is also soluble in polar solvents including a 1/1 mixture of ethanol/water. Both polymers are amorphous with excellent thermal stability (T-g (Midpoint) = 343 degrees C and 298 degrees C for P(2ADN) and P(3ADQ), respectively). P(2ADN) exhibited three prominent absorption bands in tetrahydrofuran (364, 383 and 403 nm) and is similar to that of P(3ADQ) (369, 384 and 404 nm). The solid-state Commission Internationale d'Eclairage (CIEx,y) color coordinates for illumination were (0.15, 0.10) for P(2ADN) and (0.15, 0.13) for P(3ADQ) which lied within the requirements for a true blue display color. The photoluminescence (PL) of the polymers red-shifted 16-17 nm from their respective pendant chromophore 2-methyl-9,10-di(2-naphthalenyl)anthracene (2MADN) and 2-methyl-9,10-di(3-quinolinyl)anthracene (3MADQ) and can be attributed to partial pi-pi stacking between the adjacent aromatic pendant groups in the polymer chains. The luminescences of 3MADQ and P(3ADQ) are sensitive to pH and the pK(a), for the alkalescent 3MADQ and P(3ADQ) calculated was 2.4 and 2.7, respectively. Both polymers have similar band-gap energy (E-g) between 2.88 and 2.91 eV, while the LUMO/HOMO for P(3ADQ) is shifted slightly downward -0.06 to -0.03 eV compared to P(2ADN). The mobility (mu(hole)) of the two polymers were measured to be 4.0 x 10(-7) and 10(-8) cm(2)/(V-s) for P(2ADN) and P(3ADQ), respectively. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2013.04.021
• 作为产物：
  描述：

  2-methyl-1,4,4a,9a-tetrahydroanthracene-9,10-dione 在 N-溴代丁二酰亚胺(NBS) 、 四(三苯基膦)钯 、 copper(ll) sulfate pentahydrate 、 氨 、 potassium carbonate 、 三氟乙酸 、 potassium hydroxide 、 锌 作用下， 以 四氢呋喃 、 甲醇 、 氯仿 、 水 为溶剂， 生成 2-甲基-9,10-二(2-萘基)蒽
  参考文献：
  名称：

  Synthesis and characterization of highly soluble blue emitting poly(2-vinylanthracene) with 9,10-di(2-naphthalenyl) and 9,10-di(3-quinolinyl) substituents

  摘要：

  Two new blue fluorescent polymers, poly(9,10-di(2-naphthalenyl)-2-vinylanthracene) (P(2ADN)) and poly(9,10-di(3-quinolinyl)-2-vinylanthracene) (P(3ADQ)), were polymerized from free radical solution addition polymerization with M-n = 21,500 and 15,400, respectively. The polymers are highly soluble in common organic solvents while P(3ADQ) is also soluble in polar solvents including a 1/1 mixture of ethanol/water. Both polymers are amorphous with excellent thermal stability (T-g (Midpoint) = 343 degrees C and 298 degrees C for P(2ADN) and P(3ADQ), respectively). P(2ADN) exhibited three prominent absorption bands in tetrahydrofuran (364, 383 and 403 nm) and is similar to that of P(3ADQ) (369, 384 and 404 nm). The solid-state Commission Internationale d'Eclairage (CIEx,y) color coordinates for illumination were (0.15, 0.10) for P(2ADN) and (0.15, 0.13) for P(3ADQ) which lied within the requirements for a true blue display color. The photoluminescence (PL) of the polymers red-shifted 16-17 nm from their respective pendant chromophore 2-methyl-9,10-di(2-naphthalenyl)anthracene (2MADN) and 2-methyl-9,10-di(3-quinolinyl)anthracene (3MADQ) and can be attributed to partial pi-pi stacking between the adjacent aromatic pendant groups in the polymer chains. The luminescences of 3MADQ and P(3ADQ) are sensitive to pH and the pK(a), for the alkalescent 3MADQ and P(3ADQ) calculated was 2.4 and 2.7, respectively. Both polymers have similar band-gap energy (E-g) between 2.88 and 2.91 eV, while the LUMO/HOMO for P(3ADQ) is shifted slightly downward -0.06 to -0.03 eV compared to P(2ADN). The mobility (mu(hole)) of the two polymers were measured to be 4.0 x 10(-7) and 10(-8) cm(2)/(V-s) for P(2ADN) and P(3ADQ), respectively. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2013.04.021

文献信息

• Synthesis and properties of novel 9,10-di(naphthalen-2-yl)anthracene derivatives
  作者：Ning Xiang、Xinghua Huang、Zhenyuan Xia、Guojian Tian、Jinhai Huang、Qiaochun Wang、Jianhua Su

  DOI：10.1016/j.tetlet.2016.03.048

  日期：2016.4

  known compound 9,10-di(naphthalen-2-yl)anthracene (MADN). To broaden the π-conjugated system, three units with different electronegativity were introduced and connected to the C-2 position of MADN by vinyl unit. The Suzuki reaction, the Wittig reaction, and the Heck reaction were employed to synthesize these compounds. MADN is a well-known anthracene derivative which has been widely used as blue emitter

  基于已知的化合物9,10-二（萘-2-基）蒽（MADN）设计并合成了三个新分子。为了拓宽π共轭体系，引入了三个不同电负性的单元，并通过乙烯基单元连接到MADN的C-2位。使用Suzuki反应，Wittig反应和Heck反应合成这些化合物。MADN是一种众所周知的蒽衍生物，已被广泛用作蓝色发光体。所有这些结果表明，这些新颖的MADN衍生物可能是OLED的某种潜在材料。
• 一种9,10-不对称二取代蒽衍生物的制备方法
  申请人：欧洛德(武汉)光电科技有限公司

  公开号：CN107641070B

  公开（公告）日：2020-05-22

  本发明公开了一种用于制备9,10‑不对称二取代蒽衍生物的两步合成新方法。本发明的新合成方法较文献中经常使用的三步合成方法，具有路径短，成本低的优点，而且可以很好地控制终产品的纯度，可以显著提高产物的纯度。本发明的新合成方法具有很高的商业化价值。