1-anthracen-1-yl-3-phenylurea

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 1-anthracen-1-yl-3-phenylurea
• 化学式: C₂₁H₁₆N₂O
• 分子量: 312.371
• InChiKey: BFKFTIINKCGNDH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  24
• 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：
  41.1
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  四丁基醋酸铵 、 1-anthracen-1-yl-3-phenylurea 生成
  参考文献：
  名称：

  蒽-脲与阴离子氢键配合物光诱导反应的动力学分析

  摘要：

  在乙酸根阴离子（乙酸四丁基铵，TBAAc）存在下，尿素-蒽类n PUA（n  = 1，2，9 ; PUA = 1-蒽-n-基-3-苯基脲）的瞬态吸收测量得到寿命约为100μs的瞬态物质，不受O 2的影响。寿命显示出显着的温度依赖性，这使我们能够确定ΔH ‡和ΔS ‡。Δ小号‡有较大的负值，相反，Δ ħ ‡，表明过渡形式的耗散过程是熵控制。之间的线性关系Ť ΔS ‡和ΔH ‡提出了熵-焓补偿，通常在具有氢键的宿主-客体系统中发现。这些发现使我们可以将瞬态物种指定为X，这是负责更长波长发射的基态，并得出结论，瞬态物种的耗散与基态中复合物的恢复相对应。我们提出了一种在阴离子存在下应用于脲衍生物的光化学过程的反应方案。

  DOI：

  10.1016/j.jphotochem.2012.09.011
• 作为产物：
  描述：

  氨基-9,10-蒽二酮 在 sodium tetrahydroborate 、 sodium hydroxide 作用下， 以 四氢呋喃 、 异丙醇 为溶剂， 反应 134.0h， 生成 1-anthracen-1-yl-3-phenylurea
  参考文献：
  名称：

  Kinetics of Hydrogen Bonding between Anthracene Urea Derivatives and Anions in the Excited State

  摘要：

  Urea compounds are useful anion sensors due to their hydrogen-bonding capabilities. We investigated the emissive properties of complexes consisting of urea anthracene (nPUA, n = 1, 2) host compounds and acetate anions held as guests through intermolecular hydrogen bonding. The kinetics of a new emission band formed by conformational changes in the excited singlet state were revealed. The new band is thought to arise from a charge-transfer interaction between the anthracene and urea moieties after intermolecular hydrogen-bond reconfiguration in the excited state, with rate constants of 2.4 x 10(9) and 4.0 x 10(7) s(-1) for 1PUA and 2PUA, respectively.

  DOI：

  10.1021/jp2022693

文献信息

• 10.1007/s43630-024-00598-3
  作者：Oyama, Hiroki、Nishimura, Yoshinobu

  DOI：10.1007/s43630-024-00598-3

  日期：——

  anthracen-1-yl-3-phenylurea derivatives with substituents, –CF3, –F, or –Cl, at the p-position of the phenyl group in the presence of acetate to investigate the substituent effects on the ESPT reaction and the deactivation processes of N* and T*. Kinetic analysis showed that the reverse ESPT rate constant (k−PT) depended on the respective substituents, suggesting that each substituent may influence the reverse ESPT

  荧光芳香脲化合物在乙酸根阴离子存在下经历激发态分子间质子转移 (ESPT)，从复合物 (N*) 的激发态产生互变异构体 (T*) 的激发态，从而产生双荧光。在此，我们在乙酸酯存在下对苯基对位具有取代基（-CF 3 、-F或-Cl）的蒽-1-基-3-苯基脲衍生物进行了光谱测量，以研究取代基的影响ESPT反应以及N*和T*的失活过程。动力学分析表明，反向ESPT速率常数( k −PT )取决于各自的取代基，这表明每个取代基可能对反向ESPT过程产生不同的影响。特别是，由于-F的吸电子特性是通过-I和+Iπ效应来估计的，因此-F可能具有轻微的给电子特性，并影响激发态中从T*到N*的逆过程。状态。这项研究表明，可以通过选择 ESPT 系统中的特定取代基来控制排放。  图解摘要
• Unique Hydrogen Bonds between 9-Anthracenyl Hydrogen and Anions
  作者：Ji Young Kwon、Yun Jung Jang、Sook Kyung Kim、Keun-Hyeung Lee、Jong Seung Kim、Juyoung Yoon

  DOI：10.1021/jo049281+

  日期：2004.7.1

  Unique hydrogen bonds of the 9-H of anthracene moieties in hosts 1 and 2 with fluoride and pyrophosphate ions were observed on the basis of the H-1 NMR experiments. Furthermore, hosts 1 and 2 act as a colorimetric sensor and a fluorescent chemosensor for the recognition of fluoride ion, respectively.
• Kinetics of Hydrogen Bonding between Anthracene Urea Derivatives and Anions in the Excited State
  作者：Satomi Ikedu、Yoshinobu Nishimura、Tatsuo Arai

  DOI：10.1021/jp2022693

  日期：2011.7.28

  Urea compounds are useful anion sensors due to their hydrogen-bonding capabilities. We investigated the emissive properties of complexes consisting of urea anthracene (nPUA, n = 1, 2) host compounds and acetate anions held as guests through intermolecular hydrogen bonding. The kinetics of a new emission band formed by conformational changes in the excited singlet state were revealed. The new band is thought to arise from a charge-transfer interaction between the anthracene and urea moieties after intermolecular hydrogen-bond reconfiguration in the excited state, with rate constants of 2.4 x 10(9) and 4.0 x 10(7) s(-1) for 1PUA and 2PUA, respectively.
• Kinetic analysis of photoinduced reactions in hydrogen-bonded complexes of anthracene-urea with anions
  作者：Haruki Masai、Satomi Ikedu、Yoshinobu Nishimura、Tatsuo Arai

  DOI：10.1016/j.jphotochem.2012.09.011

  日期：2012.12

  assign the transient species as X, which is the ground state responsible for longer wavelength emissions, and conclude that the dissipation of the transient species corresponded to recovery of the complex in the ground state. We propose a reaction scheme for the photochemical process applying to urea derivatives in the presence of anions.

  在乙酸根阴离子（乙酸四丁基铵，TBAAc）存在下，尿素-蒽类n PUA（n  = 1，2，9 ; PUA = 1-蒽-n-基-3-苯基脲）的瞬态吸收测量得到寿命约为100μs的瞬态物质，不受O 2的影响。寿命显示出显着的温度依赖性，这使我们能够确定ΔH ‡和ΔS ‡。Δ小号‡有较大的负值，相反，Δ ħ ‡，表明过渡形式的耗散过程是熵控制。之间的线性关系Ť ΔS ‡和ΔH ‡提出了熵-焓补偿，通常在具有氢键的宿主-客体系统中发现。这些发现使我们可以将瞬态物种指定为X，这是负责更长波长发射的基态，并得出结论，瞬态物种的耗散与基态中复合物的恢复相对应。我们提出了一种在阴离子存在下应用于脲衍生物的光化学过程的反应方案。