2,3-bis(4-hydroxyphenyl)-2-cyclopropen-1-one | 25361-95-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2,3-bis(4-hydroxyphenyl)-2-cyclopropen-1-one
• 英文别名: Bis-(p-hydroxyphenyl)-cyclopropenon；bis(4-hydroxyphenyl)cyclopropenone；2,3-Bis(4-hydroxyphenyl)cycloprop-2-enone；2,3-bis(4-hydroxyphenyl)cycloprop-2-en-1-one
• CAS: 25361-95-9
• 化学式: C₁₅H₁₀O₃
• 分子量: 238.243
• InChiKey: ZFKBQDFWAVPLSA-UHFFFAOYSA-N

物化性质

• 熔点：
  163 °C(Solv: dichloromethane (75-09-2); hexane (110-54-3))
• 沸点：
  538.0±50.0 °C(Predicted)
• 密度：
  1.450±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,3-bis(4-hydroxyphenyl)-2-cyclopropen-1-one 以 二氯甲烷 、 水 、 丙酮 为溶剂， 生成
  参考文献：
  名称：

  Photonic Amplification by a Singlet-State Quantum Chain Reaction in the Photodecarbonylation of Crystalline Diarylcyclopropenones

  摘要：

  The photochemical decarbonylation of diphenylcyclopropenone (DPCP) to diphenylacetylene (DPA) proceeds with remarkable efficiency both in solution and in the crystalline solid state. It had been previously shown that excitation to the second electronic excited state (S-2) of DPCP in solution proceeds within ca. 200 fs by an adiabatic ring-opening pathway to yield the S-2 state of DPA, which has a lifetime of ca. 8 ps before undergoing internal conversion to S-1(Takeuchi, S.; Tahara, T. J. Chem. Phys. 2004, 120, 4768). More recently, we showed that reactions by excitation to S-2 in crystalline solids proceed by a quantum chain process where the excited photoproducts transfer energy to neighboring molecules of unreacted starting material, which are able to propagate the chain. Quantum yields in crystalline suspensions revealed values of Phi(DPCP) = 3.3 +/- 0.3. To explore the generality of this reaction, and recognizing its potential as a photonic amplification system, we have synthesized nine crystalline diarylcyclopropenone derivatives with phenyl, biphenyl, naphthyl, and anthryl substituents. To quantity the efficiency of the quantum chain in the crystalline state, we determined the quantum yields of reaction for all of these compounds both in solution and in nanocrystalline suspensions. While the quantum yields of decarbonylation in solution vary from Phi = 0.0 to 1.0, seven of the nine new structures display quantum yields of reaction in the solid that are above 1. The chemical amplification that results from efficient energy transfer in the solid state, analyzed in terms of the quantum yields determined in the solid state and in solution (Phi(cryst)/Phi(soln)), reveals quantum chain amplification factors that range from 3.2 to 11.0. The remarkable mechanical response of the solid-to-solid reaction previously documented with macroscopic crystals, where large single-crystalline specimens turn into fine powders, was investigated at the nanometer scale. Experiments with dry crystals of DPCP analyzed by atomic force microscopy showed the formation of DPA in the form of isolated crystalline specimens ca. 35 nm in size.

  DOI：

  10.1021/ja9043449
• 作为产物：
  描述：

  2,3-bis(4-methoxyphenyl)cyclopropenone 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 62.66h， 以70.9%的产率得到2,3-bis(4-hydroxyphenyl)-2-cyclopropen-1-one
  参考文献：
  名称：

  以二苯基环丙烯酮为中心的聚合物，用于特定位置的CO释放和链解离

  摘要：

  摘要提出了以二苯基环丙烯酮（DPCP）为中心的聚丙烯酸甲酯（PMA）的合成和刺激反应性。以DPCP为中心的PMA可以以开关方式在紫外线下释放一氧化碳（CO）。可以通过光致发光光谱的变化来报告释放CO的过程。另外，共价嵌入交联聚氨酯中的DPCP部分也可以在紫外线下释放CO。特别地，在超声下，溶液中以DPCP为中心的PMA在酚酯键处选择性解离，并且通过D2O交换1H NMR光谱揭示了力诱导的水解反应。动力学研究表明少量的水可以提高断链率。这项工作为特定于现场的CO释放和链解离提供了一个以DPCP为中心的聚合物。

  DOI：

  10.1016/j.cclet.2019.03.053

文献信息

• Molecular Interactions Control Quantum Chain Reactions toward Distinct Photoresponsive Properties of Molecular Crystals
  作者：Yanjun Gong、Yifan Zhang、Wei Xiong、Ke Zhang、Yanke Che、Jincai Zhao

  DOI：10.1021/jacs.7b06261

  日期：2017.8.9

  crystals. The microribbons 1 and 2 having weak molecular interactions exhibited an efficient chain reaction and large mechanical photoresponses (i.e., photomelting and photodeforming), whereas the microribbons 3 and 4 with strong molecular interactions exhibited no chain reaction and mechanical morphology change. Our work presented a new way to achieve molecular crystals with enhanced mechanical photoresponses

  在这项工作中，我们制造了4个diphenylcyclopropenone（DPCP）晶体，其涉及单个分子结构编码的各种分子间相互作用1 - 4。在晶体结构分析和所得到的单晶microribbons的光响应特性的基础1 - 4，我们表明，分子间的相互作用的量值能有效控制量子链反应和DPCP晶体的光响应特性。具有弱分子相互作用的微带1和2表现出有效的链反应和较大的机械光响应（即光熔和光变形），而微带3具有强分子相互作用的4和4没有链反应和机械形态变化。我们的工作提出了一种获得具有增强的机械光响应的分子晶体的新方法。