(2E)-1,3,3-trimethyl-2-[(2E,4E)-6-(2,4,5,7-tetranitro-9H-fluoren-9-ylidene)hexa-2,4-dienylidene]-indoline | 1440539-14-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: (2E)-1,3,3-trimethyl-2-[(2E,4E)-6-(2,4,5,7-tetranitro-9H-fluoren-9-ylidene)hexa-2,4-dienylidene]-indoline
• 英文别名: (2E)-1,3,3-trimethyl-2-[(2E,4E)-6-(2,4,5,7-tetranitro-9H-fluoren-9-ylidene)hexa-2,4-dienylidene]indoline
• CAS: 1440539-14-9
• 化学式: C₃₀H₂₃N₅O₈
• 分子量: 581.541
• InChiKey: GBCWJCWBTVCZPF-UJIZWDKWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.16
• 重原子数：
  43.0
• 可旋转键数：
  7.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  175.8
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为产物：
  描述：

  2-{(1E,3E,5E)-6-[acetyl(phenyl)amino]hexa-1,3,5-trien-1-yl}-1,3,3-trimethyl-3H-indol-1-ium perchlorate 、 2,4,5,7-tetranitrofluorene 在 乙酸酐 、 三乙胺 作用下， 反应 0.05h， 以76%的产率得到(2E)-1,3,3-trimethyl-2-[(2E,4E)-6-(2,4,5,7-tetranitro-9H-fluoren-9-ylidene)hexa-2,4-dienylidene]-indoline
  参考文献：
  名称：

  Synthesis and spectral properties of merocyanine dyes based on polynitrofluorenes

  摘要：

  The di-, tetra- and hexamethinemerocyanines derived from di-, tri- and tetranitrofluorene, containing heterocyclic indolylidene residue were synthesized and their absorption spectra in the solvents of different polarity were investigated. A quantum-chemical analysis of the electronic structure of the synthesized merocyanines was performed and the types of electronic transitions in their molecules were calculated using DFT and TDDFT methods with the B3LYP/6-31G(d,p) basis. It was shown that with increasing electronacceptor properies of the fluorene core the electronic structure of the merocyanines can change from a neutral polyene to an ideal polymethine, which significantly affects the position, intensity and shape of the absorption bands, as well as vinylene shifts and deviations.

  DOI：

  10.1134/s1070363213070098

文献信息

• Synthesis and Spectral Properties of Merocyanine Dyes Derived from Tetranitrofluorene and Heterocycles of Various Electron-donating Ability
  作者：I. V. Kurdyukova、A. A. Ishchenko、N. A. Derevyanko、D. D. Mysyk

  DOI：10.1007/s10593-013-1245-x

  日期：2013.5

  Syntheses are reported for di-, tetra-, and hexamethine merocyanines derived from 2,4,5,7-tetra-nitrofluorene and heterocyclic fragments with various electron-donating ability. The absorption spectra of these compounds were studied in solvents of different polarities. A quantum-chemical analysis was carried out for the electronic structure and types of electronic transitions of these merocyanines by using the DFT and TDDFT methods in the B3LYP/6-31G(d,p) basis set. The electronic structure of these merocyanines varied from neutral polyene to polymethine and bipolar polyene with increasing electron-donating ability of the heterocyclic fragment and with solvent polarity. These differences were strongly reflected in the position, intensity, and shape of the absorption bands, vinylene shifts, and deviations, as well as the sign of solvatochromic effect.