4-ethynyl-4H-cyclopenta[1,2-b:5,4-b']dithiophene-4-ol | 1297604-04-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-ethynyl-4H-cyclopenta[1,2-b:5,4-b']dithiophene-4-ol
• 英文别名: 4-hydroxy-4-ethynylcyclopenta[2,1-b:3,4-b']dithiophene；7-Ethynyl-3,11-dithiatricyclo[6.3.0.02,6]undeca-1(8),2(6),4,9-tetraen-7-ol；7-ethynyl-3,11-dithiatricyclo[6.3.0.02,6]undeca-1(8),2(6),4,9-tetraen-7-ol
• CAS: 1297604-04-6
• 化学式: C₁₁H₆OS₂
• 分子量: 218.3
• InChiKey: LQQPYHHXURJVFU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  76.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-ethynyl-4H-cyclopenta[1,2-b:5,4-b']dithiophene-4-ol 、 溶剂黄146 在 吡啶 作用下， 以31%的产率得到4-ethynyl-4H-cyclopenta[1,2-b:5,4-b']dithiophene-4-yl acetate
  参考文献：
  名称：

  重新思考解禁：由共振能量增益驱动的新反芳香光笼。

  摘要：

  用于时空光控制的光激活化合物，例如光开关或光不稳定保护基团（PPG、光笼），在不同的研究领域中发挥着至关重要的作用。对于每种应用，需要优化多个竞争过程的参数，例如吸收光谱、在各自介质中的溶解度和/或光化学量子产率。因此，新型光化学工具的设计仍然是一项重要任务。在这项研究中，我们利用 N. Colin Baird 于 1971 年首次描述的激发态芳香性概念来研究一类基于循环基态反芳香系统的新型光笼。在量子化学计算的支持下，合成了几种硫代和氮官能化化合物，进行了光化学表征并进一步优化。选择最佳支架后，其显示出 28% 的出色解笼量子产率，实现了超过 100 nm 的红移，从而形成了坚固、易接近、可见光吸收、紧凑的新型光笼，具有干净的光反应和高量子效率。 405 nm 处 893 M-1 cm-1 的乘积 (ϵ⋅Φ)。

  DOI：

  10.1002/chem.202102351
• 作为产物：
  描述：

  4H-环戊并[2,1-B:3,4-B']二噻吩-4-酮 、 乙炔 在 正丁基锂 、 水 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 生成 4-ethynyl-4H-cyclopenta[1,2-b:5,4-b']dithiophene-4-ol
  参考文献：
  名称：

  Thienyl-Substituted Allenylideneruthenium(II) Complexes: Synthesis, Spectroscopic Characterization, and Electrochemical Studies

  摘要：

  Two propargylic alcohols incorporating a thienyl moiety were synthesized, and their subsequent reaction to form allenylideneruthenium(II) complexes is reported. The alkynol 4-hydroxy-4-ethynylcyclopenta[2,1-b:3,4-b']dithiophene (4) reacts with cis-[RuCl2(P boolean AND P)(2)] (P boolean AND P = dppm, dppe) to afford the allenylidene complexes trans-[RuCl(P boolean AND P)(2){=C=C=C(4-cyclopentadithiophene)}]PF6 (P boolean AND P = dppm, 5a; dppe, 5b). Similar reactions of cis-[RuCl2(P boolean AND P)(2)] with 1,1-di(2'-thienyl)prop-2-yn-1-ol (2) yield products consistent with formulation as an allenylideneruthenium(II) complex, although with no identifiable counteranion. In contrast the reaction of 2 with [RuClCp(dppe)] readily affords the deep purple complex [RuCp-(dppe){=C=C=C(2-thienyl)(2)}]PF6. The complexes have been characterized by spectroscopy and mass spectrometry, and a single-crystal X-ray structural determination of complex 5a was undertaken. The allenylidene complexes obtained in a pure state have also been investigated through cyclic voltammetry, and preliminary investigations illustrate their potential as synthons for organometallic polymers via electropolymerization.

  DOI：

  10.1021/om200030n

文献信息

• Thienyl-Substituted Allenylideneruthenium(II) Complexes: Synthesis, Spectroscopic Characterization, and Electrochemical Studies
  作者：George A. Koutsantonis、Phil A. Schauer、Brian W. Skelton

  DOI：10.1021/om200030n

  日期：2011.5.23

  Two propargylic alcohols incorporating a thienyl moiety were synthesized, and their subsequent reaction to form allenylideneruthenium(II) complexes is reported. The alkynol 4-hydroxy-4-ethynylcyclopenta[2,1-b:3,4-b']dithiophene (4) reacts with cis-[RuCl2(P boolean AND P)(2)] (P boolean AND P = dppm, dppe) to afford the allenylidene complexes trans-[RuCl(P boolean AND P)(2)=C=C=C(4-cyclopentadithiophene)}]PF6 (P boolean AND P = dppm, 5a; dppe, 5b). Similar reactions of cis-[RuCl2(P boolean AND P)(2)] with 1,1-di(2'-thienyl)prop-2-yn-1-ol (2) yield products consistent with formulation as an allenylideneruthenium(II) complex, although with no identifiable counteranion. In contrast the reaction of 2 with [RuClCp(dppe)] readily affords the deep purple complex [RuCp-(dppe)=C=C=C(2-thienyl)(2)}]PF6. The complexes have been characterized by spectroscopy and mass spectrometry, and a single-crystal X-ray structural determination of complex 5a was undertaken. The allenylidene complexes obtained in a pure state have also been investigated through cyclic voltammetry, and preliminary investigations illustrate their potential as synthons for organometallic polymers via electropolymerization.
• Rethinking Uncaging: A New Antiaromatic Photocage Driven by a Gain of Resonance Energy
  作者：Volker Hermanns、Maximilian Scheurer、Nils Frederik Kersten、Chahinez Abdellaoui、Josef Wachtveitl、Andreas Dreuw、Alexander Heckel

  DOI：10.1002/chem.202102351

  日期：2021.10.7

  were synthesized, photochemically characterized and further optimized, supported by quantum chemical calculations. After choosing the optimal scaffold, which shows an excellent uncaging quantum yield of 28 %, we achieved a bathochromic shift of over 100 nm, resulting in a robust, well accessible, visible light absorbing, compact new photocage with a clean photoreaction and a high quantum product (ϵ⋅Φ)

  用于时空光控制的光激活化合物，例如光开关或光不稳定保护基团（PPG、光笼），在不同的研究领域中发挥着至关重要的作用。对于每种应用，需要优化多个竞争过程的参数，例如吸收光谱、在各自介质中的溶解度和/或光化学量子产率。因此，新型光化学工具的设计仍然是一项重要任务。在这项研究中，我们利用 N. Colin Baird 于 1971 年首次描述的激发态芳香性概念来研究一类基于循环基态反芳香系统的新型光笼。在量子化学计算的支持下，合成了几种硫代和氮官能化化合物，进行了光化学表征并进一步优化。选择最佳支架后，其显示出 28% 的出色解笼量子产率，实现了超过 100 nm 的红移，从而形成了坚固、易接近、可见光吸收、紧凑的新型光笼，具有干净的光反应和高量子效率。 405 nm 处 893 M-1 cm-1 的乘积 (ϵ⋅Φ)。