rhodamine 101

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: rhodamine 101
• 英文别名: Spiro[2-benzofuran-3,16'-3-oxa-9,23-diazaheptacyclo[17.7.1.15,9.02,17.04,15.023,27.013,28]octacosa-1(27),2(17),4(15),5(28),13,18-hexaene]-1-one
• 化学式: C₃₂H₃₀N₂O₃
• 分子量: 490.602
• InChiKey: XUCXFLBOLIFZNX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  37
• 可旋转键数：
  0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  42
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  哌嗪 、 rhodamine 101 在 三甲基铝 、 4-二甲氨基吡啶 、 p-nitrophenyloxycarbonyl-Wang resin 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 甲苯 、 N,N-二甲基甲酰胺 为溶剂， 反应 36.03h， 以6%的产率得到rhodamine 101 piperazine amide
  参考文献：
  名称：

  实用的合成路线到罗丹明染料。

  摘要：

  [反应：见正文]已经开发了一种合成功能化若丹明衍生物的有效方法。可以从廉价的前体制备数克量的这些水溶性荧光团，并在不使用色谱法的情况下进行纯化。通过后续反应已安装了一系列蛋白质反应性官能团，为生物分子修饰提供了材料。对于多色应用，已开发出一种固相纯化策略，以提供具有广泛光谱特性的罗丹明衍生物。

  DOI：

  10.1021/ol035135z
• 作为产物：
  描述：

  高氯酸罗丹明640 在 sodium hydroxide 作用下， 以 甲苯 为溶剂， 生成 rhodamine 101
  参考文献：
  名称：

  Photophysics of the Lactone Form of Rhodamine 101

  摘要：

  The photophysics of the lactone form of the rhodamine 101 has been investigated in nonpolar and polar aprotic solvents. A single broad luminescence band in nonpolar or weakly polar solvents is observed from a charge-transfer (CT) state (with the dipole moment of almost-equal-to 26 D) produced in the electron-transfer reaction in the excited state. In more polar solvents a second fluorescence band appears, revealing the dissociation of the C-O lactone bond. The excited singlet state of the zwitterion (Z) is formed. Temperature-dependent measurements show that the zwitterion form is produced in all solvents; it is, however, quenched in less polar media. It has been found that the quantum efficiency of population of the Z form in the excited singlet state does not depend on the solvent and equals 0.23 +/- 0.03, which indicates purely intramolecular control of the branching into CT and zwitterion excited states. The excited state reaction in frozen solvents led to intense phosphorescence from a low lying (pi,pi*) triplet state of the Z form. The ratio of fluorescence to phosphorescence intensities of the zwitterion (1:3) in rigid glass implies a supposition that the Z form is created in singlet and triplet states according to their spin statistical factors. The results of this work force us to verify the existing views on the spectroscopy of rhodamines and the role of the solvent in photophysics of these molecules. The observed intramolecular quenching of zwitterions has been ascribed to deactivation to a higher triplet, most probably of (n,pi*) nature. We suspect this mechanism to be responsible for the thermally activated nonradiative process in rhodamines. The lack of phosphorescence of rhodamine 101 in protic solvents is explained by an increase of energy of the 3(n,pi*) state, presumably due to the hydrogen bonding. The data do not support the transition to the TICT state as a mechanism of thermally activated quenching of rhodamines.

  DOI：

  10.1021/j100064a001

文献信息

• Photoluminescent compounds and uses thereof
  申请人：StoreDot Ltd.

  公开号：US10240042B2

  公开（公告）日：2019-03-26

  This invention is directed to photoluminescent compounds based on rhodamine dyes with green emission and uses thereof for photoluminescence based devices.

  本发明涉及基于罗丹明染料的具有绿色发射的光致发光化合物及其在光致发光设备中的应用。
• RHODAMINE DERIVATIVES DYES AND USES THEREOF
  申请人：StoreDot Ltd.

  公开号：US20170137626A1

  公开（公告）日：2017-05-18

  This invention is directed to photoluminescent compounds based on rhodamine dyes with red-shifted absorption and emission maxima and uses thereof for photoluminescence based devices.
• US9771480B2
  申请人：——

  公开号：US9771480B2

  公开（公告）日：2017-09-26
• Practical Synthetic Route to Functionalized Rhodamine Dyes
  作者：Trung Nguyen、Matthew B. Francis

  DOI：10.1021/ol035135z

  日期：2003.9.1

  [reaction: see text] An efficient method for the synthesis of functionalized rhodamine derivatives has been developed. Multigram quantities of these water-soluble fluorophores can be prepared from inexpensive precursors and purified without the use of chromatography. A series of protein-reactive functional groups has been installed through subsequent reactions, providing materials for biomolecule modification

  [反应：见正文]已经开发了一种合成功能化若丹明衍生物的有效方法。可以从廉价的前体制备数克量的这些水溶性荧光团，并在不使用色谱法的情况下进行纯化。通过后续反应已安装了一系列蛋白质反应性官能团，为生物分子修饰提供了材料。对于多色应用，已开发出一种固相纯化策略，以提供具有广泛光谱特性的罗丹明衍生物。
• Photophysics of the Lactone Form of Rhodamine 101
  作者：Jerzy Karpiuk、Zbigniew R. Grabowski、Frans C. De Schryver

  DOI：10.1021/j100064a001

  日期：1994.3

  The photophysics of the lactone form of the rhodamine 101 has been investigated in nonpolar and polar aprotic solvents. A single broad luminescence band in nonpolar or weakly polar solvents is observed from a charge-transfer (CT) state (with the dipole moment of almost-equal-to 26 D) produced in the electron-transfer reaction in the excited state. In more polar solvents a second fluorescence band appears, revealing the dissociation of the C-O lactone bond. The excited singlet state of the zwitterion (Z) is formed. Temperature-dependent measurements show that the zwitterion form is produced in all solvents; it is, however, quenched in less polar media. It has been found that the quantum efficiency of population of the Z form in the excited singlet state does not depend on the solvent and equals 0.23 +/- 0.03, which indicates purely intramolecular control of the branching into CT and zwitterion excited states. The excited state reaction in frozen solvents led to intense phosphorescence from a low lying (pi,pi*) triplet state of the Z form. The ratio of fluorescence to phosphorescence intensities of the zwitterion (1:3) in rigid glass implies a supposition that the Z form is created in singlet and triplet states according to their spin statistical factors. The results of this work force us to verify the existing views on the spectroscopy of rhodamines and the role of the solvent in photophysics of these molecules. The observed intramolecular quenching of zwitterions has been ascribed to deactivation to a higher triplet, most probably of (n,pi*) nature. We suspect this mechanism to be responsible for the thermally activated nonradiative process in rhodamines. The lack of phosphorescence of rhodamine 101 in protic solvents is explained by an increase of energy of the 3(n,pi*) state, presumably due to the hydrogen bonding. The data do not support the transition to the TICT state as a mechanism of thermally activated quenching of rhodamines.