3-[p-(diethylamino)phenyl]-4-hydroxy-3-cyclobutene-1,2-dione | 429675-70-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 3-[p-(diethylamino)phenyl]-4-hydroxy-3-cyclobutene-1,2-dione
• 英文别名: 4-[4-(diethylamino)phenyl]-3-hydroxy-1,2-dioxocyclobut-3-ene；3-(4-(diethylamino)phenyl)-4-hydroxycyclobut-3-ene-1,2-dione；3-hydroxy-4-[4-(N,N-diethylamino)phenyl]cyclobutene-1,2-dione；3-[4-(Diethylamino)phenyl]-4-hydroxycyclobut-3-ene-1,2-dione
• CAS: 429675-70-7
• 化学式: C₁₄H₁₅NO₃
• 分子量: 245.278
• InChiKey: FBNVNMRCGBTJDS-UHFFFAOYSA-N

物化性质

• 沸点：
  416.3±55.0 °C(Predicted)
• 密度：
  1.322±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  57.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  bis(ethylthioethyl)phenylamine 、 3-[p-(diethylamino)phenyl]-4-hydroxy-3-cyclobutene-1,2-dione 以 甲苯 、 正丁醇 为溶剂， 以30%的产率得到C₂₈H₃₆N₂O₂S₂
  参考文献：
  名称：

  Supramolecular assembly of a new squaraine and β-cyclodextrin for detection of thiol-containing amino acids in water

  摘要：

  A new unsymmetrical aniline-based squaraine (SQ2) bearing binding unit of Hg2+ ion was designed and synthesised. SQ2 can form 1:2 inclusion complex with beta-cyclodextrin, and the resulting complex, which undergoes absorption and fluorescence bleaching upon binding Hg2+, can serve as a turn-on colorimetric or fluorescent chemosensor in organic solvent-free aqueous solution for thiol-containing amino acids with high selectivity and tunable measuring range.

  DOI：

  10.1080/10610278.2011.603730
• 作为产物：
  描述：

  4-[4-(diethylamino)phenyl]-3-chlorocyclobut-3-ene-1,2-dione 在 溶剂黄146 作用下， 以86%的产率得到3-[p-(diethylamino)phenyl]-4-hydroxy-3-cyclobutene-1,2-dione
  参考文献：
  名称：

  Synthesis of Near-Infrared Absorbing Bisquarylium Dyes Bearing Unsymmetrically Extended π-Conjugation Structures

  摘要：

  新型阳离子双菁染料3和4是通过苯并噻唑基菁染料2与一系列4-取代的3-羟基或3-乙氧基环丁-3-烯-1,2-二酮反应制备的。这些染料在近红外区域显示出大且强烈的吸收，吸收峰位置在771至815纳米范围内变化。

  DOI：

  10.1055/s-2002-20034

文献信息

• The synthesis and 1O2 photosensitization of halogenated asymmetric aniline-based squaraines
  作者：Chao Luo、Qianxiong Zhou、Guoyu Jiang、Liqing He、Baowen Zhang、Xuesong Wang

  DOI：10.1039/c0nj00949k

  日期：——

  The halogenated (brominated or iodinated) squaraines have promising potential in the application of photodynamic therapy (PDT). Though aniline-based squaraines are the most classical squaraine dyes, no halogenated derivatives with the halogen atoms directly incorporated in the conjugation skeleton of the squaraine chromophore have been reported so far. In this work, a stepwise synthetic approach, i.e. by way of the halogenated semi-squaraines, was applied successfully to prepare halogenated asymmetric aniline-based squaraines. Such a structure makes iodine atoms be able to exert significant heavy atom effect on the intersystem crossing (ISC) efficiency of the squaraine dye. As a result, the iodinated asymmetric squaraine (SQ–OH–I) exhibits a singlet oxygen (1O2) quantum yield as high as 0.54. In contrast, the 1O2 quantum yield of the non-halogenated squaraine analogue (SQ–OH) is only 0.02.

  溴化或碘化的方形染料在光动力治疗（PDT）应用中具有良好的潜力。尽管基于苯胺的方形染料是最经典的方形染料，但迄今为止尚未报道将卤素原子直接引入方形染料共轭骨架的卤素衍生物。在本研究中，成功应用了一种逐步合成的方法，即通过卤化半方形染料制备卤化不对称基于苯胺的方形染料。这种结构使碘原子能够对方形染料的系间交叉（ISC）效率施加显著的重原子效应。因此，碘化不对称方形染料（SQ–OH–I）的单重氧（1O2）量子产率高达0.54。相比之下，未卤化方形染料 аналог（SQ–OH）的1O2量子产率仅为0.02。
• Molecular Design of Boronic Acid-Functionalized Squarylium Cyanine Dyes for Multiple Discriminant Analysis of Sialic Acid in Biological Samples: Selectivity toward Monosaccharides Controlled by Different Alkyl Side Chain Lengths
  作者：Kazuki Ouchi、Christa L. Colyer、Mahmoud Sebaiy、Jin Zhou、Takeshi Maeda、Hiroyuki Nakazumi、Masami Shibukawa、Shingo Saito

  DOI：10.1021/ac504201b

  日期：2015.2.3

  with formation constant 101.7 M–1), with no such enhancement for SQ-BA dyes with longer-alkyl-chain. In addition, various enhancement factors for other monosaccharides were observed depending on the alkyl chain length. Detailed thermodynamic and NMR studies of the SQ-BA complexes revealed the unique recognition mechanism: the dye aggregate with a shorter-alkyl-chain causes the slipped parallel structure

  我们设计了一系列具有不同长度烷基链残基的硼酸官能化方酸菁菁染料（SQ-BA），适用于生物样品中唾液酸（Neu5Ac）的多判别分析（MDA）。SQ-BA染料基于疏水相互作用形成聚集体，这导致水溶液中的荧光猝灭。当硼酸与糖结合时，由于离解为发射单体复合物，荧光强度增加。我们推断，根据烷基链的长度，会诱导出不同的染料聚集体结构（H-聚集体和J-聚集体），因此单糖将以不同的方式被识别（尤其是与J的多点相互作用）-汇总）。在Neu5Ac存在下，观察到具有较短烷基链的SQ-BA染料的独特发射增强（2.4倍荧光增强；形成常数为10 1.7 M –1），对于具有更长烷基链的SQ-BA染料则没有这种增强。另外，根据烷基链长，观察到其他单糖的各种增强因子。对SQ-BA配合物的详细热力学和NMR研究揭示了独特的识别机制：具有较短烷基链的染料聚集体引起滑动的平行结构，并与Neu5Ac形成稳定的2：1配合物，这与较
• RESIN COMPOSITION, FILM, OPTICAL FILTER, IMAGE DISPLAY DEVICE, SOLID-STATE IMAGING ELEMENT, AND COMPOUND
  申请人：FUJIFILM Corporation

  公开号：US20200369890A1

  公开（公告）日：2020-11-26

  Provided are a resin composition including a compound represented by Formula (1) and a resin, a film and a filter including the resin composition, a liquid crystal display device and a solid-state imaging element including the filter, and a compound suitable as a light absorbing component of the resin composition and the filter. In Formula (1), Dye represents a colorant structural part obtained by removing n1 hydrogen atoms from a squarylium compound having a specific structure. Q 1 is a structural part in which energy levels of a highest occupied molecular orbital and a lowest unoccupied molecular orbital satisfy a specific condition. L 1 represents a divalent linking group and n1 represents an integer of 1 to 4.

  提供了一种含有由化学式（1）表示的化合物和树脂的树脂组合物，以及包括该树脂组合物的膜和过滤器，包括该过滤器的液晶显示装置和固态成像元件，以及一种适用于作为树脂组合物和过滤器的吸光成分的化合物。在公式（1）中，Dye表示通过从具有特定结构的方芘化合物中去除n1个氢原子而获得的着色剂结构部分。Q1是一种结构部分，其中最高占据分子轨道和最低未占据分子轨道的能级满足特定条件。L1表示二价连接基团，n1表示1至4的整数。
• FILTER FOR ELECTRONIC DISPLAY
  申请人：Kyowa Hakko Chemical Co., Ltd.

  公开号：EP1698916A1

  公开（公告）日：2006-09-06

  The present invention provides a filter for electronic display devices, comprising a squarylium compound represented by General Formula (I): [wherein X represents a group represented by following Formula (A): (wherein R1, R2, R3, and R4 may be the same or different and each represents a hydrogen atom, a halogen atom and the like; and R5 and R6 may be the same or different and each represent a hydrogen atom, an alkyl group optionally having subsutituent(s) and the like) and the like; and Y represents a group represented by following Formula (C): (wherein R9 represents a halogen atom, an alkyl group optionally having subsutituent(s) and the like; and R10 represents a hydrogen atom, an alkyl group optionally having subsutituent(s) and the like) and the like, and "n" represents an integer of 0 to 5].

  本发明提供了一种用于电子显示设备的滤波器，由通式 (I) 所代表的鳞片状化合物组成： [其中 X 代表下式（A）所代表的基团： (其中 R1、R2、R3 和 R4 可以相同或不同，且各自代表氢原子、卤素原子等；R5 和 R6 可以相同或不同，且各自代表氢原子、任选具有亚取代基的烷基等）等；以及 Y 代表下式（C）所代表的基团： (其中 R9 代表卤素原子、任选具有亚基的烷基等；R10 代表氢原子、任选具有亚基的烷基等）等，"n "代表 0 至 5 的整数]。
• Yang, Jun-Xiao; Chen, Wen; Zhu, Fang-Hua, Journal of Chemical Research, 2004, # 6, p. 430 - 431
  作者：Yang, Jun-Xiao、Chen, Wen、Zhu, Fang-Hua、Su, Xiao-Yu、Xie, Ru-Gang、Li, Bo、Zhang, Lin

  DOI：——

  日期：——