2-methylthio-benzo[d]-1,3-dithiolium triflate

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: 2-methylthio-benzo[d]-1,3-dithiolium triflate
• 英文别名: 2-Methylsulfanyl-1,3-benzodithiol-3-ium;trifluoromethanesulfonate
• 化学式: CF₃O₃S*C₈H₇S₃
• 分子量: 348.412
• InChiKey: RGXFDFKSZVNWHQ-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  4.02
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  147
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2,4,5,7-tetranitrofluorene 、 2-methylthio-benzo[d]-1,3-dithiolium triflate 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以83%的产率得到2-(2,4,5,7-Tetranitro-fluoren-9-ylidene)-benzo[1,3]dithiole
  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
• 作为产物：
  描述：

  1,3-Benzodithiole-2-thione 、 三氟甲烷磺酸甲酯 以 氯仿 为溶剂， 反应 1.0h， 以94%的产率得到2-methylthio-benzo[d]-1,3-dithiolium triflate
  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

• 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](.).