1-methyl-1-(3-amino)propyl-2,3,4,5-tetraphenylsilole | 865435-45-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 1-methyl-1-(3-amino)propyl-2,3,4,5-tetraphenylsilole
• 英文别名: 3-(1-Methyl-2,3,4,5-tetraphenylsilol-1-yl)propan-1-amine；3-(1-methyl-2,3,4,5-tetraphenylsilol-1-yl)propan-1-amine
• CAS: 865435-45-6
• 化学式: C₃₂H₃₁NSi
• 分子量: 457.69
• InChiKey: XJGKUAKYCPWIEL-UHFFFAOYSA-N

物化性质

• 沸点：
  611.4±55.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.73
• 重原子数：
  34
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  26
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-methyl-1-(3-amino)propyl-2,3,4,5-tetraphenylsilole 、 二硫化碳 在 三乙胺 、 对甲苯磺酰氯 、 盐酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 7.5h， 以77%的产率得到
  参考文献：
  名称：

  具有大斯托克斯位移的新型基于暗共振能量转移的荧光探针用于pH值的检测及其成像应用

  摘要：

  在本文中，我们基于暗共振能量转移（DRET）策略设计并合成了pH依赖型开启荧光探针。选择具有聚集诱导发射（AIE）性质的硅杂环戊二烯（silole）衍生物作为暗能量供体，选择具有螺环结构的若丹明B衍生物作为能量受体。归因于溶液中硅烷的非发射特性，消除了来自供体的荧光泄漏。与H +结合打开DRET过程，供体的能量在非辐射衰减之前转换为受体的荧光输出。在缓冲溶液中，探针对pH值从2.75到5的变化做出响应，斯托克斯位移最大可达220 nm。此外，成像实验表明该探针能够确定活细胞的pH波动，且细胞膜通透性好且细胞毒性低。

  DOI：

  10.1016/j.dyepig.2020.108614
• 作为产物：
  描述：

  1-methyl-2,3,4,5-tetraphenyl-1H-silole 、 丙烯胺 在 dihydrogen hexachloroplatinate 作用下， 以 甲苯 为溶剂， 反应 20.0h， 以90%的产率得到1-methyl-1-(3-amino)propyl-2,3,4,5-tetraphenylsilole
  参考文献：
  名称：

  Luminescent Silole Nanoparticles as Chemoselective Sensors for Cr(VI)

  摘要：

  Colloidal suspensions of 3-aminopropylmethyl(tetraphenyl)silole nanoparticles can be used as selective chemosensors for carcinogenic chromium(VI) analyte. Methylhydrosilole is functionalized by hydrosilation of allylamine, and the colloid is prepared by the rapid addition of water to a THF solution of the silole. The method of detection is through electron-transfer quenching of the fluorescence of the silole colloid (lambda(em) = 485 nm at 360 nm excitation) by the analytes, with hundred parts per billion detection limits. Stern-Volmer plots are linear up to 10 ppm in the case of chromium, but exhibit saturation behavior near 5-10 ppm for arsenic. Dynamic light scattering experiments and AFM measurements show the particle sizes to be around 100 nm in diameter and dependent on solvent composition, with a particle size dispersity of +/- 25%. The fluorescence lifetimes of the silole in solution and colloid are similar to 31 ps and similar to 4.3 ns, respectively, while the silole has a lifetime of 6 ns in the bulk solid. A minimum volume fraction of 80% water is necessary to precipitate the colloid from THF, and the luminescence continues to rise with higher water fractions. Colloids in a pH 7 phosphate-buffered suspension show both higher sensitivity and greater selectivity (100-fold) for CrO42- detection than for other oxoanion interferents, NO3-, NO2-, SO42-, and ClO4-.

  DOI：

  10.1021/ja052582w

文献信息

• A novel fluorescent sensor for Sn ⁴⁺ detection: Dark resonance energy transfer from silole to rhodamine
  作者：Xiuji Wang、Lijian Zhang、Shaoqin Zhuang、Meifei Huang、Yihua Gao

  DOI：10.1002/aoc.5067

  日期：——

  A novel dark resonance energy transfer (DRET) off–on cassette SR1 was constructed by coupling a silole donor with a rhodamine acceptor. Due to the intramolecular rotations of the phenyl rings, the silole fluorophore served as a dark donor in solution state and fluorescence leakage from the donor emission could be avoided. Binding with Sn4+ ion induced the ring‐opening of the rhodamine acceptor, thus

  新型的暗共振能量转移（DRET）盒式SR1是通过将Silole供体与若丹明受体偶联而构建的。由于苯环的分子内旋转，甲硅烷荧光团在溶液状态下用作深色供体，可以避免来自供体发射的荧光泄漏。与Sn 4+离子的结合导致若丹明受体的开环，从而增加了供体的发射光谱与受体的吸收光谱之间的重叠。开启DRET，能量从硅烷供体转移到若丹明受体。罗丹明受体的发射是通过最大198nm的大斯托克斯位移实现的。该传感器对Sn 4+具有良好的灵敏度和选择性通过在SR1和Sn 4+之间形成1：1的络合物形成甲醇溶液中的其他金属离子。这项研究为基于罗丹明的传感器向斯托克斯位移大的金属离子的开发提供了一种新方法。
• Fluorescence Turn-On Detection of DNA and Label-Free Fluorescence Nuclease Assay Based on the Aggregation-Induced Emission of Silole
  作者：Ming Wang、Deqing Zhang、Guanxin Zhang、Yanli Tang、Shu Wang、Daoben Zhu

  DOI：10.1021/ac801020v

  日期：2008.8.1

  optical probe for fluorescence turn-on detection of DNA and label-free fluorescence nuclease assay. The fluorescence of 1 increases largely upon mixing with DNA, in particular for long DNA, indicating that 1 can be used for fluorescence turn-on detection of DNA. More interestingly, 1 can be employed to follow the DNA cleavage process by nuclease. Therefore, a label-free fluorescence nuclease assay method

  通过利用硅溶胶的聚集诱导发射特征，设计并合成具有铵基的化合物1，以开发用于DNA的荧光开启检测和无标记荧光核酸酶测定的新型光学探针。与DNA混合后，荧光1大大增加，特别是对于长DNA而言，表明1可用于DNA的荧光开启检测。更有趣的是，可以采用1跟随核酸酶的DNA切割过程。因此，用1成功建立了无标记的荧光核酸酶测定方法。此外，这种无标记的荧光测定法还可用于核酸酶的抑制剂筛选。鉴于其简单，易操作，灵敏性和成本效益，
• Fluorescence enhancement upon gelation and thermally-driven fluorescence switches based on tetraphenylsilole-based organic gelators
  作者：Ming Wang、Deqing Zhang、Guanxin Zhang、Daoben Zhu

  DOI：10.1016/j.cplett.2009.05.029

  日期：2009.6

  Two new organic gelators 1 and 2 based on the silole (silacyclopentadiene) framework were designed with the end to develop switchable fluorescent organogels, by making use of the aggregation-induced emission (AIE) feature of silole derivatives. As for other silole derivatives, compounds 1 and 2 exhibited AIE behavior as indicated by the significant fluorescence enhancement by introducing water to the THF solutions. Compounds 1 and 2 can gel hexane, methylcyclohexane and heptane. Large fluorescence enhancement was observed for compounds 1 and 2 after gelation. Moreover, their fluorescence intensities can be changed reversibly accompanying the gel-solution transition through alternating cooling and heating. Therefore, thermally-driven fluorescence switches can be achieved with organogels based on 1 and 2. (c) 2009 Elsevier B.V. All rights reserved.
• A novel dark resonance energy transfer-based fluorescent probe with large Stokes shift for the detection of pH and its imaging application
  作者：Xiuji Wang、Lijian Zhang、Qin Li、Yihua Gao

  DOI：10.1016/j.dyepig.2020.108614

  日期：2020.10

  process and energy of donor is converted to the acceptor's fluorescence output before non-radiative decay. The probe responds to pH variation from 2.75 to 5 in buffer solutions with a Stokes shift up to 220 nm. In addition, imaging experiments suggest that the probe is capable of determining pH fluctuations in live cells with good cell membrane permeability and low cytotoxicity.

  在本文中，我们基于暗共振能量转移（DRET）策略设计并合成了pH依赖型开启荧光探针。选择具有聚集诱导发射（AIE）性质的硅杂环戊二烯（silole）衍生物作为暗能量供体，选择具有螺环结构的若丹明B衍生物作为能量受体。归因于溶液中硅烷的非发射特性，消除了来自供体的荧光泄漏。与H +结合打开DRET过程，供体的能量在非辐射衰减之前转换为受体的荧光输出。在缓冲溶液中，探针对pH值从2.75到5的变化做出响应，斯托克斯位移最大可达220 nm。此外，成像实验表明该探针能够确定活细胞的pH波动，且细胞膜通透性好且细胞毒性低。
• Luminescent Silole Nanoparticles as Chemoselective Sensors for Cr(VI)
  作者：Sarah J. Toal、Kelsey A. Jones、Douglas Magde、William C. Trogler

  DOI：10.1021/ja052582w

  日期：2005.8.24

  Colloidal suspensions of 3-aminopropylmethyl(tetraphenyl)silole nanoparticles can be used as selective chemosensors for carcinogenic chromium(VI) analyte. Methylhydrosilole is functionalized by hydrosilation of allylamine, and the colloid is prepared by the rapid addition of water to a THF solution of the silole. The method of detection is through electron-transfer quenching of the fluorescence of the silole colloid (lambda(em) = 485 nm at 360 nm excitation) by the analytes, with hundred parts per billion detection limits. Stern-Volmer plots are linear up to 10 ppm in the case of chromium, but exhibit saturation behavior near 5-10 ppm for arsenic. Dynamic light scattering experiments and AFM measurements show the particle sizes to be around 100 nm in diameter and dependent on solvent composition, with a particle size dispersity of +/- 25%. The fluorescence lifetimes of the silole in solution and colloid are similar to 31 ps and similar to 4.3 ns, respectively, while the silole has a lifetime of 6 ns in the bulk solid. A minimum volume fraction of 80% water is necessary to precipitate the colloid from THF, and the luminescence continues to rise with higher water fractions. Colloids in a pH 7 phosphate-buffered suspension show both higher sensitivity and greater selectivity (100-fold) for CrO42- detection than for other oxoanion interferents, NO3-, NO2-, SO42-, and ClO4-.