3,7-di-p-tolyl-pyrano[4,3-c]pyran-1,5-dione | 134949-97-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 3,7-di-p-tolyl-pyrano[4,3-c]pyran-1,5-dione
• 英文别名: 3,7-Di-p-tolyl-pyrano[4,3-c]pyran-1,5-dion；3,7-Bis(4-methylphenyl)pyrano[4,3-c]pyran-1,5-dione
• CAS: 134949-97-6
• 化学式: C₂₂H₁₆O₄
• 分子量: 344.367
• InChiKey: JCSQUWVASFBDRP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,7-di-p-tolyl-pyrano[4,3-c]pyran-1,5-dione 在 sodium hydroxide 作用下， 以 1,4-二氧六环 、 水 为溶剂， 生成
  参考文献：
  名称：

  Bowden, Keith; Etemadi, Razieh; Ranson, Richard J., Journal of the Chemical Society. Perkin transactions II, 1991, # 5, p. 743 - 746

  摘要：

  DOI：
• 作为产物：
  描述：

  (E)-5,5'-di-p-tolyl-[3,3']bifurylidene-2,2'-dione 在 sodium acetate 作用下， 以 乙二醇 为溶剂， 生成 3,7-di-p-tolyl-pyrano[4,3-c]pyran-1,5-dione
  参考文献：
  名称：

  REARRANGEMENT OF SUBSTITUTED (E)-5,5?-DIPHENYLBIFURANYLIDENEDIONES TO 3,7-DIPHENYLPYRANO[4,3-c]PYRAN-1,5-DIONES

  摘要：

  The rate coefficients for the rearrangement of substituted (E)-5,5'-diphenylbifuranylidenediones to form the corresponding 3,7-diphenylpyrano[4,3-c]pyran-1,5-diones in ethane-1,2-diol at 30.0 degrees C, catalysed by sodium acetate, were determined, For the unsubstituted dione, the rate coefficients for there arrangement in various alcohols at 30.0 degrees C, and for three at 59.8 degrees C, were measured, The reactions were first order in both substrate and acetate anion, Rate coefficients were also measured for the catalysis of the rearrangement of the unsubstituted dione in ethanol and ethane-1,2-diol at 30.0 degrees C by a series of sodium meta/para-substituted benzoates, Bronsted-type correlations for the latter give alpha approximate to 1.2. Substrate substitutent effects on the rates of rearrangement of the diones were not marked, A good correlation was found between the rates of rearrangement of the unsubstituted dione and the solvent effect parameter E-T(30). This and other evidence indicated a probable mechanism involving a rapid pre-equilibrium between the substrate diones and the carboxylate anion, followed by the formation of an s-trans-enolate anion, The latter rotates to the s-cis isomer, which then intramolecularly attacks the second lactone ring, The process is then repeated with the product dione resulting from loss of the carboxylate anion. (C) 1997 by John Wiley & Sons, Ltd.

  DOI：

  10.1002/(sici)1099-1395(199704)10:4<191::aid-poc888>3.0.co;2-5

文献信息

• Singlet Fission in Pechmann Dyes: Planar Chromophore Design and Understanding
  作者：Aswathy V. Girija、Weixuan Zeng、William K. Myers、Rachel C. Kilbride、Daniel T. W. Toolan、Cheng Zhong、Felix Plasser、Akshay Rao、Hugo Bronstein

  DOI：10.1021/jacs.4c00288

  日期：2024.7.10

  combined with double-bond conformation to establish simple qualitative design rules for predicting fundamental optical properties without the need for computational modeling. By investigating two Pechmann dye isomers, we demonstrate that although their planarity and degree of charge transfer are similar, singlet fission is active in the isomer with a trans-conformation, while the cis-isomer exhibits

  有机发色团中的单线态裂变具有将光伏效率提高到超出单结极限的潜力。单线态裂变材料最基本的要求是其第一单线态和三线态激发态之间具有较大的能隙。识别此类化合物并不简单，可以通过计算筛选或通过对先前已知的裂变材料进行细微修改来完成。在这里，我们提出了一种利用基态和激发态芳香性与双键构象相结合的方法来建立简单的定性设计规则，用于预测基本光学特性，而无需计算建模。通过研究两种佩希曼染料异构体，我们证明，尽管它们的平面度和电荷转移程度相似，但反式构象的异构体中单线态裂变活跃，而顺式异构体对极化过程表现出更大的有利性，使用超快实验进行了验证和电子自旋共振光谱。我们的结果提供了一种新的设计视角，为根据单线态裂变或三线态-三线态湮灭等特定应用定制光电系统提供了合理的框架
• Chovin, Annales de Chimie (Cachan, France), 1938, vol. <11> 9, p. 447,491
  作者：Chovin

  DOI：——

  日期：——