9,10-bis(4-methoxystyryl)anthracene | 136384-80-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 9,10-bis(4-methoxystyryl)anthracene
• 英文别名: Anthracene, 9,10-bis[2-(4-methoxyphenyl)ethenyl]-；9,10-bis[(E)-2-(4-methoxyphenyl)ethenyl]anthracene
• CAS: 136384-80-0
• 化学式: C₃₂H₂₆O₂
• 分子量: 442.557
• InChiKey: VQBOLXYNPLCQBJ-YHARCJFQSA-N

物化性质

• 沸点：
  663.8±45.0 °C(Predicted)
• 密度：
  1.189±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.9
• 重原子数：
  34
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  9,10-bis(4-methoxystyryl)anthracene 在 potassium tert-butylate 、 溴 作用下， 生成 9,10-双(4-甲氧基苯基乙炔)蒽
  参考文献：
  名称：

  Nakatsuji, Shin'ichi; Matsuda, Kosei; Uesugi, Yukiko, Journal of the Chemical Society. Perkin transactions I, 1992, # 7, p. 755 - 758

  摘要：

  DOI：
• 作为产物：
  描述：

  4-甲氧基苯乙烯 、 9,10-二溴蒽 在 potassium phosphate 、 palladium diacetate 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 24.0h， 以65%的产率得到9,10-bis(4-methoxystyryl)anthracene
  参考文献：
  名称：

  Novel Fluorescent pH Sensors and a Biological Probe Based on Anthracene Derivatives with Aggregation-Induced Emission Characteristics

  摘要：

  Three functionalized 9,10-distyrylanthracene (DSA) derivatives, namely, 9,10-bis(4-hydroxystyryl)anthracene (2), 9,10-bis{4-[2-(diethylamino)ethoxy]styryl}anthracene (4), and 9,10-bis{4-[2-(N,N,N-triethylammonium)ethoxy]-styryl}anthracene dibromide (5), were synthesized and their fluorescence properties were investigated. The three DSA derivatives possess a typical aggregation-induced emission (ALE) property (i.e., they are nonluminescent in dilute solutions but are efficiently fluorescent as induced by molecular aggregation). Different ALE properties were tuned through molecular structure control. Dye 2 is a phenol-moiety-containing compound, which shows aggregation at pH values smaller than 10, resulting in a high fluorescence intensity. Thus, dye 2 has a pK(a) of 9.94. 4 is an amine-containing compound that starts to aggregate at slightly basic conditions, resulting in a pK(a) of 6.90. Dye 5 is an ammonium-salt-containing compound. Because it is very soluble in water, this compound has no Al E phenomenon but can interact strongly with protein or DNA to amplify its emission. Therefore, 5 is a fluorescent turn "on" biological probe for protein and DNA detection and it is also selective, which works for native BSA and et DNA but not their denatured forms. Therefore, we not only developed a few new compounds showing the A I E phenomena but also controlled the A E through environmental stimulation and demonstrated that the new Al E molecules are suitable for pH and biomacromolecule sensing.

  DOI：

  10.1021/la904727t

文献信息

• Nakatsuji, Shin'ichi; Matsuda, Kosei; Uesugi, Yukiko, Journal of the Chemical Society. Perkin transactions II, 1991, # 6, p. 861 - 867
  作者：Nakatsuji, Shin'ichi、Matsuda, Kosei、Uesugi, Yukiko、Nakashima, Kenichiro、Akiyama, Shuzo、et al.

  DOI：——

  日期：——
• Nakatsuji, Shin'ichi; Matsuda, Kosei; Uesugi, Yukiko, Journal of the Chemical Society. Perkin transactions I, 1992, # 7, p. 755 - 758
  作者：Nakatsuji, Shin'ichi、Matsuda, Kosei、Uesugi, Yukiko、Nakashima, Kenichiro、Akiyama, Shuzo、Fabian, Walter

  DOI：——

  日期：——
• Novel Fluorescent pH Sensors and a Biological Probe Based on Anthracene Derivatives with Aggregation-Induced Emission Characteristics
  作者：Hongguang Lu、Bin Xu、Yujie Dong、Feipeng Chen、Yaowen Li、Zaifang Li、Jiating He、Hui Li、Wenjing Tian

  DOI：10.1021/la904727t

  日期：2010.5.4

  Three functionalized 9,10-distyrylanthracene (DSA) derivatives, namely, 9,10-bis(4-hydroxystyryl)anthracene (2), 9,10-bis4-[2-(diethylamino)ethoxy]styryl}anthracene (4), and 9,10-bis4-[2-(N,N,N-triethylammonium)ethoxy]-styryl}anthracene dibromide (5), were synthesized and their fluorescence properties were investigated. The three DSA derivatives possess a typical aggregation-induced emission (ALE) property (i.e., they are nonluminescent in dilute solutions but are efficiently fluorescent as induced by molecular aggregation). Different ALE properties were tuned through molecular structure control. Dye 2 is a phenol-moiety-containing compound, which shows aggregation at pH values smaller than 10, resulting in a high fluorescence intensity. Thus, dye 2 has a pK(a) of 9.94. 4 is an amine-containing compound that starts to aggregate at slightly basic conditions, resulting in a pK(a) of 6.90. Dye 5 is an ammonium-salt-containing compound. Because it is very soluble in water, this compound has no Al E phenomenon but can interact strongly with protein or DNA to amplify its emission. Therefore, 5 is a fluorescent turn "on" biological probe for protein and DNA detection and it is also selective, which works for native BSA and et DNA but not their denatured forms. Therefore, we not only developed a few new compounds showing the A I E phenomena but also controlled the A E through environmental stimulation and demonstrated that the new Al E molecules are suitable for pH and biomacromolecule sensing.