trans-2-methyl-9-(2'-methyl-9'H-thioxanthene-9'-ylideene)-9H-thioxanthene | 142561-04-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻喃类
• 英文名称: trans-2-methyl-9-(2'-methyl-9'H-thioxanthene-9'-ylideene)-9H-thioxanthene
• 英文别名: 2,2’-dimethyl-9,9’-bisthioxanthylidene；(9E)-2-methyl-9-(2-methylthioxanthen-9-ylidene)thioxanthene
• CAS: 142561-04-4
• 化学式: C₂₈H₂₀S₂
• 分子量: 420.599
• InChiKey: WEHLOVDVXGHBMD-BYYHNAKLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  30
• 可旋转键数：
  0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  50.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  trans-2-methyl-9-(2'-methyl-9'H-thioxanthene-9'-ylideene)-9H-thioxanthene 在 六氟磷酸钾 作用下， 以 乙腈 为溶剂， 以25%的产率得到
  参考文献：
  名称：

  发光的可逆三态转换：电致变色和光致变色行为的新转折

  摘要：

  报道了来自光/电致变色取代的双噻吨亚基的完全可逆的三态蓝/红/关发射。二甲基-和二甲氧基-双-噻吨亚基的最稳定（反折叠）构象异构体的蓝色发光可以通过光化学转化为亚稳定（同步折叠）构象异构体而关闭，并通过热回复到反-折叠状态。bis-thiaxanthylium dication 的红色发光可以通过在大约 1.0 和 1.2 V vs SCE 的同步和反折叠构象异构体的氧化打开，并通过在大约 0.35 V vs SCE 还原关闭或变为蓝色。

  DOI：

  10.1021/ja064423y
• 作为产物：
  描述：

  2-甲基-9H-噻吨-9-酮 在 草酰氯 、 铜 作用下， 以 xylene 为溶剂， 反应 7.0h， 生成 trans-2-methyl-9-(2'-methyl-9'H-thioxanthene-9'-ylideene)-9H-thioxanthene
  参考文献：
  名称：

  Sterically overcrowded alkenes; synthesis, resolution and circular dichroism studies of substituted bithioxanthylidenes

  摘要：

  Bithioxanthylidenes with small substituents at positions 2 and 2' have been synthesized and resolved by chiral HPLC. The X-ray molecular structure of 9-(2'-methyl-9'H-thioxanthene-9'-ylidene)-9H-xanthene (17) confirms the folded form of these molecules. UV and CD studies of several bithioxanthylidenes are presented. The CD spectra of these molecules can be described qualitatively by subtracting the CD spectra of both differently sensed helices (M and P) present in the molecule, which can be distinguished by the substituents at positions 2 and 2'.

  DOI：

  10.1016/s0957-4166(00)80349-3

文献信息

• Fast synthesis and redox switching of di- and tetra-substituted bisthioxanthylidene overcrowded alkenes
  作者：Brian P. Corbet、Marco B. S. Wonink、Ben L. Feringa

  DOI：10.1039/d1cc03098a

  日期：——

  A rapid and efficient method for the synthesis of overcrowded alkenes using (trimethylsilyl)diazomethane provides a range of substituted bisthioxanthylidenes. We show large conformational redox switching from folded to orthogonal states, which tolerates many substitution patterns. The facile access to bisthioxanthylidene switches with the potential for further functionalization, in combination with

  使用(三甲基甲硅烷基)重氮甲烷快速有效地合成过度拥挤的烯烃的方法提供了一系列取代的双硫代亚甲基。我们展示了从折叠状态到正交状态的大构象氧化还原转换，这可以容忍许多取代模式。容易获得具有进一步功能化潜力的二硫杂蒽开关，与可靠的氧化还原化学相结合，为电化学响应系统的设计提供了重要机会。
• Sterically overcrowded alkenes; synthesis, resolution and circular dichroism studies of substituted bithioxanthylidenes
  作者：Wolter F. Jager、Ben de Lange、Anne Marie Schoevaars、Fré van Bolhuis、Ben L. Feringa

  DOI：10.1016/s0957-4166(00)80349-3

  日期：1993.7

  Bithioxanthylidenes with small substituents at positions 2 and 2' have been synthesized and resolved by chiral HPLC. The X-ray molecular structure of 9-(2'-methyl-9'H-thioxanthene-9'-ylidene)-9H-xanthene (17) confirms the folded form of these molecules. UV and CD studies of several bithioxanthylidenes are presented. The CD spectra of these molecules can be described qualitatively by subtracting the CD spectra of both differently sensed helices (M and P) present in the molecule, which can be distinguished by the substituents at positions 2 and 2'.
• Reversible Three-State Switching of Luminescence:  A New Twist to Electro- and Photochromic Behavior
  作者：Wesley R. Browne、Michael M. Pollard、Ben de Lange、Auke Meetsma、Ben L. Feringa

  DOI：10.1021/ja064423y

  日期：2006.9.1

  The fully reversible three-state blue/red/off emission from photo-/electrochromic substituted bis-thiaxanthylidenes is reported. The blue luminescence of the most stable (anti-folded) conformer of dimethyl- and dimethoxy-bis-thiaxanthylidene can be switched off by photochemical conversion to the meta-stable (syn-folded) conformer and switched on again by thermal reversion to the anti-folded state.

  报道了来自光/电致变色取代的双噻吨亚基的完全可逆的三态蓝/红/关发射。二甲基-和二甲氧基-双-噻吨亚基的最稳定（反折叠）构象异构体的蓝色发光可以通过光化学转化为亚稳定（同步折叠）构象异构体而关闭，并通过热回复到反-折叠状态。bis-thiaxanthylium dication 的红色发光可以通过在大约 1.0 和 1.2 V vs SCE 的同步和反折叠构象异构体的氧化打开，并通过在大约 0.35 V vs SCE 还原关闭或变为蓝色。