8H-naphto[2,3-c]thioxanthen-8-one | 1315465-45-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 8H-naphto[2,3-c]thioxanthen-8-one
• 英文别名: naphto[2,3-c]thioxanthen-8-one；Naphtho[2,3-c]thioxanthen-8-one；naphtho[2,3-c]thioxanthen-8-one
• CAS: 1315465-45-2
• 化学式: C₂₁H₁₂OS
• 分子量: 312.392
• InChiKey: MZBXHKWOLXAZEF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  23
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  蒽 、 硫代水杨酸 在 硫酸 、 溶剂黄146 作用下， 反应 4.5h， 以8%的产率得到8H-naphto[2,3-c]thioxanthen-8-one
  参考文献：
  名称：

  π扩展的噻吨酮-在可见光激发下，设计基于镧系元素的发光探针的噻吨酮敏化剂的三重态水平。

  摘要：

  用于光学生物成像的基于镧系元素的明亮探针必须依靠天线原理，其中以镧系元素为中心的激发态是通过复杂的敏化过程形成的。通过以致敏发色团为中心的三重态实现对镧系元素中心发射的有效敏化。在此，噻吨酮生色团的三重态通过扩展π系统来调节。合成并表征了三种噻吨酮生色团-噻吨酮，苯并[c]噻吨酮和萘[2,3-c]噻吨酮。发现三重态能量和寿命按预期改变，并且发现两种染料是适合（（iii）发光的敏化剂。制备了噻吨酮和苯并[c]噻吨酮的反应性衍生物，并将其偶联至1,4,7,10-四氮杂环十二烷-1,4，7-三乙酸（DO3A）镧系元素结合口袋。研究了所得euro（iii）配合物的光物理性质和光学生物成像性能。结论是，尽管高能学有利于有效的敏化，但溶液结构却并非如此。虽然发现该复合物亲脂性太高，无法用作光学生物成像的有效发光探针，但我们成功地证明了在405 nm激发后使用（（iii）发光进行生物成像。

  DOI：

  10.1002/cplu.201900309

文献信息

• Enhancement of the Two-Photon Initiating Efficiency of a Thioxanthone Derivative through a Chevron-Shaped Architecture
  作者：Jean-Pierre Malval、Ming Jin、Fabrice Morlet-Savary、Hélène Chaumeil、Albert Defoin、Olivier Soppera、Teodora Scheul、Michel Bouriau、Patrice L. Baldeck

  DOI：10.1021/cm200595y

  日期：2011.8.9

  We investigated the one- and two-photon excitation properties of a new hybrid anthracene thioxanthone (ANTX) system, which was assembled into a chevron-shaped molecular architecture. Such a geometrical association first preserves the high efficiency of the free radical photoinitiator and leads, in the same time, to a strong increase in the two-photon absorption (2PA) cross section by more than a factor of 30 as compared to thioxanthone (TX). A four-state model was required to fit the 2PA spectrum of ANTX, which clearly undergoes a strong enhancement in the low-frequency region. As a consequence, ANTX constitutes a suitable two-photon initiating chromophore with a much higher efficiency as TX used as reference. At lambda(exc) = 710 nm for instance, we showed that the two-photon polymerization threshold of ANTX is five times lower with respect to that of TX. Additionally, we demonstrated by the fabrication of three-dimensional microstructures that this new hybrid system remains two-photon activable when excited at wavelengths near its one-photon absorption region as suggested by the sum overstates model. We also show that this new two-photon initiator exhibits a higher reactivity than a diaminofluorene derivative, which is commonly used in two-photon polymerization.
• π‐Expanded Thioxanthones – Engineering the Triplet Level of Thioxanthone Sensitizers for Lanthanide‐Based Luminescent Probes with Visible Excitation
  作者：Charlotte Nybro Dansholm、Anne Kathrine R. Junker、Lea G. Nielsen、Nicolaj Kofod、Robert Pal、Thomas Just Sørensen

  DOI：10.1002/cplu.201900309

  日期：2019.12

  complex sensitization process. Efficient sensitization of lanthanide-centred emission occurs via triplet states centred on the sensitizing chromophore. Here, the triplet state of thioxanthone chromophores is modulated by extending the π-system. Three thioxanthone chromophores-thioxanthone, benzo[c]thioxanthone, and naphtho[2,3-c]thioxanthone were synthesised and characterised. The triplet state energies

  用于光学生物成像的基于镧系元素的明亮探针必须依靠天线原理，其中以镧系元素为中心的激发态是通过复杂的敏化过程形成的。通过以致敏发色团为中心的三重态实现对镧系元素中心发射的有效敏化。在此，噻吨酮生色团的三重态通过扩展π系统来调节。合成并表征了三种噻吨酮生色团-噻吨酮，苯并[c]噻吨酮和萘[2,3-c]噻吨酮。发现三重态能量和寿命按预期改变，并且发现两种染料是适合（（iii）发光的敏化剂。制备了噻吨酮和苯并[c]噻吨酮的反应性衍生物，并将其偶联至1,4,7,10-四氮杂环十二烷-1,4，7-三乙酸（DO3A）镧系元素结合口袋。研究了所得euro（iii）配合物的光物理性质和光学生物成像性能。结论是，尽管高能学有利于有效的敏化，但溶液结构却并非如此。虽然发现该复合物亲脂性太高，无法用作光学生物成像的有效发光探针，但我们成功地证明了在405 nm激发后使用（（iii）发光进行生物成像。