2,4-bis<4-(dibutylamino)phenyl>squaraine | 230306-78-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 2,4-bis<4-(dibutylamino)phenyl>squaraine
• 英文别名: 2,4-Bis[4-(dibutylamino)phenyl]-3-hydroxycyclobut-2-en-1-one
• CAS: 230306-78-2
• 化学式: C₃₂H₄₆N₂O₂
• 分子量: 490.729
• InChiKey: JSORIBDTVITVJN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.2
• 重原子数：
  36
• 可旋转键数：
  16
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  43.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,4-bis<4-(dibutylamino)phenyl>squaraine 在 吡啶 、 三氯氧磷 作用下， 以 二氯甲烷 为溶剂， 生成 2,4-bis-(4-dibutylamino-phenyl)-3-ethylamino-cyclobut-2-enone
  参考文献：
  名称：

  Facile preparative redox chemistry of bis(4-dialkylaminophenyl)squaraine dyes

  摘要：

  Bis(4-dialkylaminophenyl)squaraine dyes are readily reduced in solution by borohydride to give alkali soluble leuco compounds, which exist in the 3-hydroxy-2,4-(4-dialkylaminophenyl)cyclobutenone tautomeric form. The leuco dyes can be oxidised rapidly back to the squaraine dye, thus providing a means of temporarily solubilising the squaraine dye in water. The leuco compounds undergo Substitution reactions typical of vinylogous carboxylic acids. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)01857-9
• 作为产物：
  描述：

  bis[4-(N,N-dibutylamino)phenyl]squaraine 在 sodium tetrahydroborate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 2,4-bis<4-(dibutylamino)phenyl>squaraine
  参考文献：
  名称：

  Facile preparative redox chemistry of bis(4-dialkylaminophenyl)squaraine dyes

  摘要：

  Bis(4-dialkylaminophenyl)squaraine dyes are readily reduced in solution by borohydride to give alkali soluble leuco compounds, which exist in the 3-hydroxy-2,4-(4-dialkylaminophenyl)cyclobutenone tautomeric form. The leuco dyes can be oxidised rapidly back to the squaraine dye, thus providing a means of temporarily solubilising the squaraine dye in water. The leuco compounds undergo Substitution reactions typical of vinylogous carboxylic acids. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)01857-9

文献信息

• Aggregation-Induced Linear and Non-Linear Optical Properties of Four Hydroxy-Substituted Analogues of 2,4-Bis[4-(dibutylamino)phenyl]squaraine
  作者：Geoffrey J. Ashwell、Patricia C. Williamson、Andrew Green、Gurmit S. Bahra、Christopher R. Brown

  DOI：10.1071/c98059

  日期：——

  Langmuir films of the title compound, 2,4-bis[4-(dibutylamino)phenyl]squaraine, Sq0, and its substituted analogues, Sq1 (monohydroxy) to Sq4 (tetrahydroxy), exhibit three well defined phases at the air–water interface: λmax 525–550 nm (H-aggregate); 660–670 nm (intermediate); 760–770 nm (J-aggregate). The monolayer spectra are influenced by the surface pressure and the number of hydroxy substituents and, when the monolayers are transferred to a solid substrate, there is a correlation between the linear and non-linear optical behaviour of the Langmuir-Blodgett films. Second-harmonic generation has been observed even though the unit molecular structures of two analogues, Sq0 and Sq4, are centric. The behaviour is aggregation-induced and there is evidence that the dyes associate in dilute solution. The electrospray ionization mass spectra exhibit peaks with high mass/charge (m/z) ratios; the data conform to the dimeric aggregate and, for solutions of two or more squaraines, corroborate the existence of heteromolecular associates.

  标题化合物的朗缪尔薄膜、 2,4-双[4-（二丁基氨基）苯基]方卡因（Sq0）及其取代的 类似物 Sq1（单羟基）至 Sq4（四羟基）在空气-水界面上显示出三种明确的 相：λmax 525-550 nm（H-聚集体）；660-670 nm（中间体）；760-770 纳米（J-聚集体）。单层光谱受表面压力和羟基取代基数量的影响 单层光谱受表面压力和羟基取代基数量的影响。 当单层被转移到固体基底上时，其线性和非线性光学行为之间存在相关性。 朗缪尔-布洛杰特薄膜的线性和非线性光学行为之间存在关联。 即使两种类似物的单位分子结构为 Sq0 和 Sq4 这两种类似物的单位分子结构都是居中的，但还是观察到了二次谐波的产生。这种行为是 聚合引起的，而且有证据表明染料在稀释溶液中会结合在一起。 溶液中发生关联。电喷雾电离质谱显示出高 质量/电荷（m/z）比的峰值；数据符合 数据符合二聚聚合体的特征，而对于两种或两种以上的方形染料溶液，数据也证实了 异分子结合体的存在。