(E)-5,5′-di(thiophen-2-yl)-3,3′-bi[thiophen-3(2H)-ylidene]-2,2′-dione | 1438289-29-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: (E)-5,5′-di(thiophen-2-yl)-3,3′-bi[thiophen-3(2H)-ylidene]-2,2′-dione
• 英文别名: (3E)-3-(2-oxo-5-thiophen-2-ylthiophen-3-ylidene)-5-thiophen-2-ylthiophen-2-one
• CAS: 1438289-29-2
• 化学式: C₁₆H₈O₂S₄
• 分子量: 360.502
• InChiKey: YNRYAGIIEGTFPV-MDZDMXLPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  141
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-溴噻吩 、 2,2′-di-tert-butoxy-5,5′-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,3′-bithiophene 在 2-双环己基膦-2',6'-二甲氧基联苯 、 potassium phosphate 、 palladium diacetate 、 三氟乙酸 作用下， 以 四氢呋喃 、 水 、 氯苯 为溶剂， 以8 mg的产率得到(E)-5,5′-di(thiophen-2-yl)-3,3′-bi[thiophen-3(2H)-ylidene]-2,2′-dione
  参考文献：
  名称：

  (E)-5,5′-Di(thiophen-2-yl)-3,3′-bi[thiophen-3(2H)-ylidene]-2,2′-diones—from conspicuous blue impurities to “quasi-metallic” golden-bronze crystals

  摘要：

  (E)-5,5′-二(噻吩-2-基)-3,3′-双[噻吩-3(2H)-亚甲基]-2,2′-二酮(1a) 引起了多位化学家的关注，他们在各种反应中偶然发现了它作为微量副产物。我们在此报告了这种强烈蓝色染料的首次有意合成（λmax 635 nm; εmax 32,400 L cm⁻¹ mol⁻¹）。我们基于TDDFT的预测证明，1a以前被错误地分配为结构异构体，并对之前报告的可见吸收数据进行了更正。我们采用发散合成路线，方便地制备了配备戊基（1b）和丁基硫醇（1c）基团的1a衍生物（五步的产率为3–7%）。1b和1c的晶体展现出迷人的“准金属”金铜色光泽。这种效果在分子晶体中比较罕见，仅在最强烈的染料中观察到。

  DOI：

  10.1039/c3ob40373d

文献信息

• Organic Materials with Special Optical Effects
  申请人：Centre National de la Recherche Scientifique (CNRS)

  公开号：US20190337885A1

  公开（公告）日：2019-11-07

  The present invention relates to a compound of the following formula (I). The invention also relates to uses thereof as a chromophore as such or for building pigments displaying special optical effects, including metal-like reflection.
• Amphiphilic and Mesogenic Organic Dyes for Tailor-Made Reflective Low-Dimensional Materials
  申请人：Sorbonne Universite

  公开号：US20210122742A1

  公开（公告）日：2021-04-29

  The present invention relates to a compound of the following formula (I): The invention also relates to uses thereof as dye or pigment, notably as a luster pigment. The invention relates also to a reflective or photonic or nanophotonic or optoelectronic device comprising a compound of the invention. The invention relates also to a metal-like reflective coating, a metal-like particle or an organic-based metal-like liquid film comprising a compound of the invention.
• (E)-5,5′-Di(thiophen-2-yl)-3,3′-bi[thiophen-3(2H)-ylidene]-2,2′-diones—from conspicuous blue impurities to “quasi-metallic” golden-bronze crystals
  作者：Nicholas R. Evans、Andrew J. P. White

  DOI：10.1039/c3ob40373d

  日期：——

  (E)-5,5′-Di(thiophen-2-yl)-3,3′-bi[thiophen-3(2H)-ylidene]-2,2′-dione (1a) has caught the eye of several chemists who have encountered it as a trace by-product in a variety of reactions. We report here the first deliberate synthesis of this intense blue dye (λmax 635 nm; εmax 32 400 L cm−1 mol−1). We prove on the basis of predictions made with TDDFT that 1a has previously been misassigned as a structural isomer and we correct the visible absorption data that was reported. Derivatives of 1a equipped with pentyl (1b) and butylsulfanyl (1c) groups are readily prepared with our divergent synthetic route (3–7% yield over five steps). Crystals of 1b and 1c exhibit an attractive “quasi-metallic” golden-bronze lustre. This effect is rare in molecular crystals and is observed only with the most intense dyes.

  (E)-5,5′-二(噻吩-2-基)-3,3′-双[噻吩-3(2H)-亚甲基]-2,2′-二酮(1a) 引起了多位化学家的关注，他们在各种反应中偶然发现了它作为微量副产物。我们在此报告了这种强烈蓝色染料的首次有意合成（λmax 635 nm; εmax 32,400 L cm⁻¹ mol⁻¹）。我们基于TDDFT的预测证明，1a以前被错误地分配为结构异构体，并对之前报告的可见吸收数据进行了更正。我们采用发散合成路线，方便地制备了配备戊基（1b）和丁基硫醇（1c）基团的1a衍生物（五步的产率为3–7%）。1b和1c的晶体展现出迷人的“准金属”金铜色光泽。这种效果在分子晶体中比较罕见，仅在最强烈的染料中观察到。