9-(4-phenyl-1,3-dithiol-2-ylidene)-2,4,5,7-tetranitrofluorene

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 9-(4-phenyl-1,3-dithiol-2-ylidene)-2,4,5,7-tetranitrofluorene
• 英文别名: 4-Phenyl-2-(2,4,5,7-tetranitrofluoren-9-ylidene)-1,3-dithiole
• 化学式: C₂₂H₁₀N₄O₈S₂
• 分子量: 522.475
• InChiKey: FGKYPYQBKXEZKA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  36
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  234
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  4-苯基-1,3-二硫杂-2-硫代-环戊-4-烯 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.08h， 生成 9-(4-phenyl-1,3-dithiol-2-ylidene)-2,4,5,7-tetranitrofluorene
  参考文献：
  名称：

  Electron Acceptors of the Fluorene Series. 9.¹ Derivatives of 9-(1,2-Dithiol-3-ylidene)-, 9-(1,3-Dithiol-2-ylidene)-, and 9-(1,3-Selenathiol-2-ylidene)fluorenes:  Synthesis, Intramolecular Charge Transfer, and Redox Properties

  摘要：

  The synthesis and physical properties of four series of novel fluorene push-pull compounds (4-7) of the D-pi-A type with intramolecular charge transfer (from 1,3- and 1,2-dithiole and 1,3-selenathiole donor (D) moieties) are described. The nature of the heteroatom (S or Se) in the donor fragment has no effect on the maxima of intramolecular absorption bands (lambda(ICT)), whereas a change of position of the heteroatoms in the dithiole moiety from 1,3 to 1,2 leads to a substantial bathochromic shift in lambda(ICT). Solvatochromism, thermochromism, and negative halochromism in these compounds are demonstrated. Cyclic voltammograms of 4-7 exhibit two, separate, single-electron reversible redox waves, the potentials of which (as well as the ICT energies in the molecules) are quantitatively described by sigma(p)(-) constants of the substituents in the fluorene ring. Compounds 4-7 exhibit reversible salt formation in sulfuric acid, and for compound 5g in diluted sulfuric acid an additional absorption in the near-IR region has been observed that we attribute to radical species formation from the equilibrium [5g-H](+) + 5g reversible arrow 5g(.+) + [5g-H](.).

  DOI：

  10.1021/jo990100r

文献信息

• Mysyk, Dmitrii D.; Perepichka, Igor F., Phosphorus, Sulfur and Silicon and the Related Elements, 1994, vol. 96, # 1-4, p. 527 - 530
  作者：Mysyk, Dmitrii D.、Perepichka, Igor F.

  DOI：——

  日期：——
• Mysyk Dmitrii D., Perepichka Igor F., Phosph., Sulfur and Silicon and Relat. Elem, 95-96 (1994) N 1-4, S 527-52+
  作者：Mysyk Dmitrii D., Perepichka Igor F.

  DOI：——

  日期：——
• Electron Acceptors of the Fluorene Series. 9.¹ Derivatives of 9-(1,2-Dithiol-3-ylidene)-, 9-(1,3-Dithiol-2-ylidene)-, and 9-(1,3-Selenathiol-2-ylidene)fluorenes:  Synthesis, Intramolecular Charge Transfer, and Redox Properties
  作者：Dmitrii D. Mysyk、Igor F. Perepichka、Dmitrii F. Perepichka、Martin R. Bryce、Anatolii F. Popov、Leonid M. Goldenberg、Adrian J. Moore

  DOI：10.1021/jo990100r

  日期：1999.9.1

  The synthesis and physical properties of four series of novel fluorene push-pull compounds (4-7) of the D-pi-A type with intramolecular charge transfer (from 1,3- and 1,2-dithiole and 1,3-selenathiole donor (D) moieties) are described. The nature of the heteroatom (S or Se) in the donor fragment has no effect on the maxima of intramolecular absorption bands (lambda(ICT)), whereas a change of position of the heteroatoms in the dithiole moiety from 1,3 to 1,2 leads to a substantial bathochromic shift in lambda(ICT). Solvatochromism, thermochromism, and negative halochromism in these compounds are demonstrated. Cyclic voltammograms of 4-7 exhibit two, separate, single-electron reversible redox waves, the potentials of which (as well as the ICT energies in the molecules) are quantitatively described by sigma(p)(-) constants of the substituents in the fluorene ring. Compounds 4-7 exhibit reversible salt formation in sulfuric acid, and for compound 5g in diluted sulfuric acid an additional absorption in the near-IR region has been observed that we attribute to radical species formation from the equilibrium [5g-H](+) + 5g reversible arrow 5g(.+) + [5g-H](.).