5-(dibutylamino)benzene-1,3-diol | 210880-91-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 5-(dibutylamino)benzene-1,3-diol
• 英文别名: 5-(Dibutylamino)benzene-1,3-diol
• CAS: 210880-91-4
• 化学式: C₁₄H₂₃NO₂
• 分子量: 237.342
• InChiKey: VBJBPWOTBNZYDG-UHFFFAOYSA-N

物化性质

• 沸点：
  376.8±12.0 °C(Predicted)
• 密度：
  1.062±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  43.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  巴豆酸 、 5-(dibutylamino)benzene-1,3-diol 以 甲苯 、 正丁醇 为溶剂， 以2.5%的产率得到
  参考文献：
  名称：

  Discovery of Novel Dyes with Absorption Maxima at 1.1 μm

  摘要：

  During the process of developing organic molecules that match the wavelengths used in optical communications, we have discovered a new class of dyes, with absorption maxima at 1.1 mum, and clarified their molecular structures. The synthesis of this class of dyes was supposed to involve unexpected intramolecular tandem reactions, and the effect of alkyl substituents on such a synthesis was investigated. As a result, an effective alkyl-substituent structure for realizing a high synthetic yield and good solubility in organic solvents was found. Furthermore, thin films made of such a highly soluble dye were fabricated by solution-coating, and they exhibited a red-shifted absorption band with a maximum at approximately 1.3 mum, indicating the formation of J-like aggregates. The third-order nonlinear optical susceptibility chi(3) of these thin films at 1.3 mum, which is the wavelength used in optical communications, was measured by the Z-scan technique. The magnitude of chi(3) reaches approximately 10-7 esu. These results suggest that the solution-coated thin films of this type of dye are potential materials for optical switching at 1.3 mum and for other nonlinear optical applications.

  DOI：

  10.1021/ja0209666
• 作为产物：
  描述：

  间苯三酚 、 二正丁胺 以 甲苯 、 正丁醇 为溶剂， 反应 8.0h， 以32.4%的产率得到5-(dibutylamino)benzene-1,3-diol
  参考文献：
  名称：

  通过三羟基取代策略在不对称方蓝染料上制备的光伏器件

  摘要：

  一系列带有两个，三个或四个羟基（-OH）取代基的不对称芳烃1,3-方酸（USQ）衍生物，即USQ-2-OH，USQ-3-OH或USQ-4-OH，分别设计和合成，并研究了羟基数目对USQs光电性能的影响。尽管这三种化合物具有相似的UV / Vis吸收和HOMO能级，但以USQ-3-OH作为电子给体材料的固溶体异质结（BHJ）小分子有机太阳能电池的最高功率转换效率为6.07％ ，这可能主要归因于较高的空穴迁移率和较小的相分离。还值得注意的是，短路电流（J基于USQ-3-OH的设备的sc）高达14.95 mA cm -2，这是迄今为止基于方酸的BHJ太阳能电池报道的最高J sc值。结果还表明，方酸菁染料上更多的-OH取代基不一定会导致更好的光伏性能。

  DOI：

  10.1002/chem.201705140

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。
• Search for Squaraine Derivatives That Can Be Sublimed without Thermal Decomposition
  作者：Minquan Tian、Makoto Furuki、Izumi Iwasa、Yasuhiro Sato、Lyong Sun Pu、Satoshi Tatsuura

  DOI：10.1021/jp013698r

  日期：2002.5.1

  To search for sublimable squaraine (SQ) dyes for fabricating thin films under vacuum, we have synthesized a series of 2,4-bis[4-(N,N-dialkylamino)-2,6-dihydroxyphenyl]squaraines [SQ(OH)(4)] and studied their properties. The investigation of the behavior of their Langmuir films at the air-water interface revealed that SQ(OH)(4) molecules with branched N-alkyl groups such as sec-butyls and isobutyls have larger limiting areas and tend to form J-aggregates in the monolayers, whereas molecules with straight N-alkyl chains have smaller limiting areas and are apt to form H-aggregates. This behavior is attributable to the much larger steric hindrance of the branched N-butyl groups than that of the straight ones. The thermal stability of these dyes was investigated by differential thermal analysis (DTA) and thermogravimetry (TG), and their sublimation ability was evaluated through heating under vacuum. As a result, we verified that the four hydroxyls at the 2',6'-positions of the two phenyl rings significantly enhanced the thermal stability and the sublimation ability of an anilino SQ dye molecule, and the introduction of branched N-butyls further promoted the sublimation ability of the target SQ(OH)(4) molecules. These phenomena may be attributed to the intramolecular hydrogen bonding between the hydroxyls and the CO groups of the four-membered ring, and the much larger intermolecular repulsive force between branched N-alkyls, respectively. In particular, the SQ(OH)(4) dye with four N-isobutyls could be sublimed without any decomposition. These results suggest that SQ(OH)(4) molecule with branched N-butyls is the most effective structure for realizing a high sublimation ability. Furthermore, pure SQ dye thin films have been successfully fabricated by molecular beam deposition of the SQ(OH)(4) dye with four N-isobutyls. The vacuum-deposited thin films of such SQ dyes have potential applications in various fields such as electrophotography, solar energy conversion, optical recording, and nonlinear optics.
• Photovoltaic Devices Prepared through a Trihydroxy Substitution Strategy on an Unsymmetrical Squaraine Dye
  作者：Jianglin Wu、Changfeng Si、Yao Chen、Lin Yang、Bin Hu、Guo Chen、Zhiyun Lu、Yan Huang

  DOI：10.1002/chem.201705140

  日期：2018.3.2

  arene‐1,3‐squaraine (USQ) derivatives with two, three, or four hydroxy (−OH) substituents, namely, USQ‐2‐OH, USQ‐3‐OH, or USQ‐4‐OH, respectively, were designed and synthesized, and the effect of the number of hydroxy groups on the optoelectronic properties of USQs were investigated. Despite the three compounds having similar UV/Vis absorption and HOMO energy levels, solution‐processed bulk‐heterojunction

  一系列带有两个，三个或四个羟基（-OH）取代基的不对称芳烃1,3-方酸（USQ）衍生物，即USQ-2-OH，USQ-3-OH或USQ-4-OH，分别设计和合成，并研究了羟基数目对USQs光电性能的影响。尽管这三种化合物具有相似的UV / Vis吸收和HOMO能级，但以USQ-3-OH作为电子给体材料的固溶体异质结（BHJ）小分子有机太阳能电池的最高功率转换效率为6.07％ ，这可能主要归因于较高的空穴迁移率和较小的相分离。还值得注意的是，短路电流（J基于USQ-3-OH的设备的sc）高达14.95 mA cm -2，这是迄今为止基于方酸的BHJ太阳能电池报道的最高J sc值。结果还表明，方酸菁染料上更多的-OH取代基不一定会导致更好的光伏性能。
• Discovery of Novel Dyes with Absorption Maxima at 1.1 μm
  作者：Minquan Tian、Satoshi Tatsuura、Makoto Furuki、Yasuhiro Sato、Izumi Iwasa、Lyong Sun Pu

  DOI：10.1021/ja0209666

  日期：2003.1.1

  During the process of developing organic molecules that match the wavelengths used in optical communications, we have discovered a new class of dyes, with absorption maxima at 1.1 mum, and clarified their molecular structures. The synthesis of this class of dyes was supposed to involve unexpected intramolecular tandem reactions, and the effect of alkyl substituents on such a synthesis was investigated. As a result, an effective alkyl-substituent structure for realizing a high synthetic yield and good solubility in organic solvents was found. Furthermore, thin films made of such a highly soluble dye were fabricated by solution-coating, and they exhibited a red-shifted absorption band with a maximum at approximately 1.3 mum, indicating the formation of J-like aggregates. The third-order nonlinear optical susceptibility chi(3) of these thin films at 1.3 mum, which is the wavelength used in optical communications, was measured by the Z-scan technique. The magnitude of chi(3) reaches approximately 10-7 esu. These results suggest that the solution-coated thin films of this type of dye are potential materials for optical switching at 1.3 mum and for other nonlinear optical applications.