N-(2-hydroxyethyl)benzo[k,l]thioxanthene-3,4-dicarboximide | 52559-43-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: N-(2-hydroxyethyl)benzo[k,l]thioxanthene-3,4-dicarboximide
• 英文别名: 2-(2-hydroxy-ethyl)-thioxantheno[2,1,9-def]isoquinoline-1,3-dione；N-(2-Hydroxyethyl)benzothioxanthen-3,4-dicarboximid；14-(2-Hydroxyethyl)-8-thia-14-azapentacyclo[10.6.2.02,7.09,19.016,20]icosa-1(19),2,4,6,9,11,16(20),17-octaene-13,15-dione
• CAS: 52559-43-0
• 化学式: C₂₀H₁₃NO₃S
• 分子量: 347.394
• InChiKey: NMTZRXOITBLOMT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  82.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(2-hydroxyethyl)benzo[k,l]thioxanthene-3,4-dicarboximide 在 五甲基二乙烯三胺 、 铜 、 三乙胺 、 copper(I) bromide 作用下， 以 氯仿 为溶剂， 生成 2-(N-benzo[k,l]thioxanthene-3,4-dicarboximide)ethyl 2-(2,2,5-trimethyl-4-pyrenyl-3-azahexane-3-oxy)propionate
  参考文献：
  名称：

  Spectral properties of bichromophoric probes based on pyrene and benzothioxanthene in solution and in polymer matrices

  摘要：

  The new initiator for controlled radical polymerization labeled with highly fluorescent chromophores was prepared. Highly fluorescent chromophores, such as pyrene and benzo[k,l]thioxanthene (BTX), were used for fluorescent labeling. The chromophores were combined with nitroxide on 2,2,5-trimethyl-4-phenyl-3-azahexane-3-nitroxide (TIPNO), which is one of the best systems for mediating the radical polymerization of olefins. The spectral properties of a labeled initiator were measured in solution and in polymer matrix. In the absorption spectra of the bichromophoric initiator there is a broad band with a maximum in the range 450-485 nm depending on the medium. This band corresponds to the BTX moiety, whereas the band with vibrational structure at 320-345 nm arises from the pyrene structural unit. The emission spectra of the probes, recorded at an excitation of 480 nm in solution and in the polymer matrices exhibit a broad band in the range 490-525 nm and it is red-shifted in polar media. Excitation of the labeled initiator in the region of the maximum absorption of pyrene results exclusively in emission due to BTX which is caused by efficient transfer of the excitation energy from pyrene to the benzothioxanthene chromophore. Quenching of the fluorescence of the donor chromophore pyrene moiety of the labeled initiator was observed in solution and in the polymer matrices, and this process is primarily intra-molecular. The quantum yield of florescence of the labeled initiator is very high in all the studied environments and is between 0.5 and 1 depending on the polarity of medium. Both chromophores exhibit fluorescence, but the lifetimes of the fluorescence are very different. The lifetime is 100-400 ns for pyrene and is 4-8 ns for benzothioxanthene. The intermolecular quenching rate constant of 3.6 x 10(10) dm(3) mol(-1) s(-1) was determined from the Stern-Volmer plot for the quenching of the decay of pyrene with the BTXD model dye. Based on the intermolecular quenching rate of the pyrene-BTXD, the rate of intramolecular energy transfer from pyrene to the BTX chromophore in this bichromophoric initiator was estimated to be greater than 10(11) s(-1). (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jphotochem.2013.06.017
• 作为产物：
  描述：

  4-(2-Aminophenylthio)-N-(3-hydroxyethyl)-1,8-naphthalimid 生成 N-(2-hydroxyethyl)benzo[k,l]thioxanthene-3,4-dicarboximide
  参考文献：
  名称：

  Grayshan,P.H. et al., Journal of Heterocyclic Chemistry, 1974, vol. 11, p. 33 - 38

  摘要：

  DOI：

文献信息

• [EN] OLIGOMERIC DYES AND PREPARATION THEREOF<br/>[FR] COLORANTS OLIGOMERES ET LEUR PREPARATION
  申请人：3M INNOVATIVE PROPERTIES CO

  公开号：WO2004024830A1

  公开（公告）日：2004-03-25

  The invention provides a method for preparing an oligomeric dye by reacting a first component oligomer, having a carbon-carbon backbone, comprising a plurality of polymerized monomer units comprising pendant reactive nucleophilic or electrophilic functional groups; and a dye component having a co-reactive functional group.These oligomeric dyes are suitable for use as additives to impart coloration or fluorescence to thermoplastic polymers, particularly olefinic polymers. The oligomeric dyes of the present invention advantageously are compatible in polymers where conventional dyes often have poor compatibility or solubility.

  该发明提供了一种制备寡聚染料的方法，通过反应第一组份寡聚体，其具有碳-碳骨架，包括含有众多聚合单体单元的，具有侧链反应性亲核或亲电性功能基团的；以及含有共反应功能基团的染料组份。这些寡聚染料适用于用作添加剂，为热塑性聚合物，特别是烯烃聚合物赋予色彩或荧光。本发明的寡聚染料在传统染料常常具有较差的兼容性或溶解性的聚合物中具有优势的兼容性。
• Labeled tackifiers
  申请人：Chong Ching Wah

  公开号：US20080009573A1

  公开（公告）日：2008-01-10

  Dye-labeled tackifiers increase dye solubility/compatibility and provide an improved means of introducing dyes into products such as inks, adhesives and coatings. When the dyes are radiation absorbing dyes, the dye-labeled tackifiers can serve as thermal transducers, and can be used in applications where it is required to cause a thermoplastic material to melt or to soften, for example a hot-melt composition.

  染料标记的粘合剂可以增加染料的溶解性/兼容性，并提供了一种改善的方法将染料引入产品中，例如油墨、粘合剂和涂料。当染料是辐射吸收染料时，染料标记的粘合剂可以作为热传感器，可用于需要使热塑性材料熔化或软化的应用中，例如热熔组合物。