2-(3',3'-Dimethyl-6-nitrospiro[chromene-2,2'-indole]-1'-yl)ethyl 5-(dithiolan-3-yl)pentanoate | 929886-82-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二硫杂环戊烷
• 英文名称: 2-(3',3'-Dimethyl-6-nitrospiro[chromene-2,2'-indole]-1'-yl)ethyl 5-(dithiolan-3-yl)pentanoate
• 英文别名: 2-(3',3'-dimethyl-6-nitrospiro[chromene-2,2'-indole]-1'-yl)ethyl 5-(dithiolan-3-yl)pentanoate
• CAS: 929886-82-8
• 化学式: C₂₈H₃₂N₂O₅S₂
• 分子量: 540.704
• InChiKey: PSSPSOMQDGLMNS-UHFFFAOYSA-N

物化性质

• 熔点：
  116-117 °C
• 沸点：
  679.5±55.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  37
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  135
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-(3',3'-Dimethyl-6-nitrospiro[chromene-2,2'-indole]-1'-yl)ethyl 5-(dithiolan-3-yl)pentanoate 以 二氯甲烷 为溶剂， 生成 2-[3,3-Dimethyl-2-[2-(3-nitro-6-oxocyclohexa-2,4-dien-1-ylidene)ethylidene]indol-1-yl]ethyl 5-(dithiolan-3-yl)pentanoate
  参考文献：
  名称：

  Luminescence Modulation with Semiconductor Quantum Dots and Photochromic Ligands

  摘要：

  我们依靠二硫环戊烷锚定基团，在镉硒锌核壳量子点表面附着了一种光致变色的螺吡喃。在由此产生的组件中，光致变色成分的可逆性相互转换激活和抑制了从激发量子点到配体有色态的能量转移途径。因此，随着螺吡喃的光诱导着色，发光强度降低了 45%，而在配体热再异构化之后，发光强度又恢复到原来的值。

  DOI：

  10.1071/ch05332
• 作为产物：
  描述：

  2-[3,3-Dimethyl-2-[2-(3-nitro-6-oxocyclohexa-2,4-dien-1-ylidene)ethylidene]indol-1-yl]ethyl 5-(dithiolan-3-yl)pentanoate 以 二氯甲烷 为溶剂， 生成 2-(3',3'-Dimethyl-6-nitrospiro[chromene-2,2'-indole]-1'-yl)ethyl 5-(dithiolan-3-yl)pentanoate
  参考文献：
  名称：

  Luminescence Modulation with Semiconductor Quantum Dots and Photochromic Ligands

  摘要：

  我们依靠二硫环戊烷锚定基团，在镉硒锌核壳量子点表面附着了一种光致变色的螺吡喃。在由此产生的组件中，光致变色成分的可逆性相互转换激活和抑制了从激发量子点到配体有色态的能量转移途径。因此，随着螺吡喃的光诱导着色，发光强度降低了 45%，而在配体热再异构化之后，发光强度又恢复到原来的值。

  DOI：

  10.1071/ch05332

文献信息

• Photo-responsive spiropyran monolayer protected gold nanorod
  作者：Jingjing Cao、Shuaifan Wu、Baoqi Zhai、Qiaochun Wang、Jing Li、Xiang Ma

  DOI：10.1016/j.dyepig.2013.11.017

  日期：2014.4

  The spiropyran monolayer covalently protected gold nanorod (GNR) hybrid was prepared and well characterized for the first time, which was stable, soluble and photo-responsive under certain light irradiation in organic solvent. The photochromism of the densely packed spiropyran monolayer on the surface of GNRs was found having effect on the surface plasmonic resonance (SPR) absorption of gold nanorods, namely inducing the intensity change of the two plasma absorption peaks at 786 and 551 nm of the GNR hybrids. The functionalization of this organic-inorganic GNR hybrid and the photo-tuning of its SPR absorption properties, especially in the not only UV-Vis range but also near-infrared (NIR) spectral area would make important and interesting sense in the area of functional hybrid nanomaterial. (C) 2013 Elsevier Ltd. All rights reserved.
• Characterizing the Photoinduced Switching Process of a Nitrospiropyran Self-Assembled Monolayer Using In Situ Sum Frequency Generation Spectroscopy
  作者：Tamim A. Darwish、Yujin Tong、Michael James、Tracey L. Hanley、Qiling Peng、Shen Ye

  DOI：10.1021/la302204f

  日期：2012.10.2

  Sum frequency generation (SFG) vibrational spectroscopy is employed to investigate the reversible, photoinduced spiro -> merocyanine isomerization of a self-assembled monolayer, the result of attachment of nitrospiropyran to a gold surface using a dithiolane anchoring group. The attachment of these molecular "alligator clips" to spiropyran molecules provide an easily accessible method to self-assemble a robust monolayer of spiropyran on a gold surface, which allows photoswitching of the spiropyran units. Probing the symmetric and antisymmetric stretching modes of the nitro group allows the determination of the structural orientation of the charged moiety with respect to the surface normal as well as the isomerization rates under photoinduced switching conditions. The photoisomerization of the spiropyran SAM on the gold surface is much faster than the rates of switching spiropyrans in a solid crystalline form, and the rate of thermal relaxation of the opened to closed form in this study is found to be on the same time scale as the relaxation of spiropyran when present in solutions with polar solvents.
• Luminescence Modulation with Semiconductor Quantum Dots and Photochromic Ligands
  作者：Massimiliano Tomasulo、Ibrahim Yildiz、Françisco M. Raymo

  DOI：10.1071/ch05332

  日期：——

  We have attached a photochromic spiropyran to the surface of CdSe–ZnS core–shell quantum dots, relying on a dithiolane anchoring group. In the resulting assembly, the reversible interconversion of the photochromic component activates and suppresses an energy transfer pathway from the excited quantum dots to the coloured state of the ligand. As a result, the luminescence intensity decreases by 45% with the photoinduced colouration of the spiropyran and returns to the original value after the thermal reisomerization of the ligand.

  我们依靠二硫环戊烷锚定基团，在镉硒锌核壳量子点表面附着了一种光致变色的螺吡喃。在由此产生的组件中，光致变色成分的可逆性相互转换激活和抑制了从激发量子点到配体有色态的能量转移途径。因此，随着螺吡喃的光诱导着色，发光强度降低了 45%，而在配体热再异构化之后，发光强度又恢复到原来的值。