3-phenyl-3-(α-naphthyl)-3H-naphtho[2,1-b]pyran | 1227951-27-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 3-phenyl-3-(α-naphthyl)-3H-naphtho[2,1-b]pyran
• 英文别名: 3-Naphthalen-1-yl-3-phenylbenzo[f]chromene；3-naphthalen-1-yl-3-phenylbenzo[f]chromene
• CAS: 1227951-27-0
• 化学式: C₂₉H₂₀O
• 分子量: 384.477
• InChiKey: PYMDIOSVGCVOEY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  30
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.03
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-phenyl-3-(α-naphthyl)-3H-naphtho[2,1-b]pyran 以 乙腈 为溶剂， 反应 0.01h， 生成
  参考文献：
  名称：

  Modification of a photochromic 3-aryl-3-(α-naphthalene)-3H-naphtho[2,1-b]pyran system with a fast fading speed in solution and in a rigid polymer matrix

  摘要：

  我们已经证明，3-芳基-3-(δ-萘)-3H-萘并[2,1-b]吡喃光致变色系统在环境温度下的光稳定状态下显示出很大的光密度。本文介绍了一种在溶液和刚性聚合物基体中改变这种光致变色系统快速消退速度的策略。研究发现，3-芳基-3-(δ-萘)-3H-萘并[2,1-b]吡喃在常温下的褪色速度主要取决于芳基 3-(δ-萘)-3H-萘并[2,1-b]吡喃 3 位上所附取代基团的性质和位置。在芳基的 3 位对位上连接电子捐赠基团时，有色形式的褪色速度会明显加快。进一步的研究发现：(1) 强电子供能基团比弱电子供能基团更有利于快速褪色；(2) 连接在萘环对位上的电子供能基团比连接在苯环对位上的电子供能基团更有利于快速褪色；(3) 在萘环和苯环的对位上都有电子供能基团时，溶液和刚性聚合物基体中的褪色速度都会显著提高。

  DOI：

  10.1039/c1jm10139k
• 作为产物：
  描述：

  以 乙腈 为溶剂， 生成 3-phenyl-3-(α-naphthyl)-3H-naphtho[2,1-b]pyran
  参考文献：
  名称：

  A strategy for the design of photochromic naphthopyrans with large optical density at photosteady state and fast fading speed at ambient temperature in the dark

  摘要：

  研究人员描述了一种光致变色萘系化合物，在这种化合物中，有色形式的光密度和褪色速度都显著提高。3 芳基-3-(α-萘)-3H-萘并[2,1-b]吡喃具有热稳定性，在环境温度下可获得较大的有色光密度。通过在α-萘基团上连接烷氧基，有色形式的褪色速度大大加快，而且褪色速度随着烷氧基链长度的增加而加快。该体系的通用性既有利于设计光密度大、在常温下褪色速度快的萘分子，也有利于其应用。

  DOI：

  10.1039/c000610f

文献信息

• Photochromic Properties of Naphthopyrans – PMMA Thin Film
  作者：Kunpeng Guo、Yi Chen

  DOI：10.1080/15421400802697566

  日期：2009.3.19

  A class of naphthopyran derivatives (3a-10a) with electron-donating and electron-acceptor substituent is prepared by condensation of 1,2-diaryl-2-propyn-1-ol with beta-naphthol in the presence of pyridinium para-toluenesulfonate (PPTS) as catalyst. All compounds go ring-opening isomerization in polymethylmethacrylate (PMMA) matrix with UV light irradiation (30 watt) and the maximum absorption of ring-opening isomers is at the range of 426-556 nm. Ring-opening isomers are completely back to ring-closing isomers when samples are kept in darkness, the bleach rate of ring-opening isomers in PMMA film increased significantly when temperature is more than 45 degrees C. Fatigue testing showed that no significant change of optical density was detected after 10 cycles.
• A strategy for the design of photochromic naphthopyrans with large optical density at photosteady state and fast fading speed at ambient temperature in the dark
  作者：Kunpeng Guo、Yi Chen

  DOI：10.1039/c000610f

  日期：——

  A photochromic naphthopyran system in which both optical density and fading speed of colored forms are significantly increased has been described. 3-Aryl-3-(α-naphthalene)-3H-naphtho[2,1-b]pyrans showed thermal stability, and a large optical density of colored forms was obtained at ambient temperature. By attachment of an alkoxyl group to the α-naphthalene group, the fading speed of colored forms was dramatically increased, and the fading speed was increased with increase of the length of alkoxyl chain. The generic nature of the system is beneficial for both the design of naphthopyran molecules with large optical density and fast fading speed at ambient temperature and applications.

  研究人员描述了一种光致变色萘系化合物，在这种化合物中，有色形式的光密度和褪色速度都显著提高。3 芳基-3-(α-萘)-3H-萘并[2,1-b]吡喃具有热稳定性，在环境温度下可获得较大的有色光密度。通过在α-萘基团上连接烷氧基，有色形式的褪色速度大大加快，而且褪色速度随着烷氧基链长度的增加而加快。该体系的通用性既有利于设计光密度大、在常温下褪色速度快的萘分子，也有利于其应用。
• Modification of a photochromic 3-aryl-3-(α-naphthalene)-3H-naphtho[2,1-b]pyran system with a fast fading speed in solution and in a rigid polymer matrix
  作者：Shulie Han、Yi Chen

  DOI：10.1039/c1jm10139k

  日期：——

  We have demonstrated that 3-aryl-3-(α-naphthalene)-3H-naphtho[2,1-b]pyrans photochromic system shows large optical density at photosteady state at ambient temperature. In this paper, we describe a strategy for modifying this photochromic system with a fast fading speed in both solution and in a rigid polymer matrix. It is found that the nature and position of the substituted groups attached to the aryl moiety at the 3-position play a key role in determining the fading speed of 3-aryl-3-(α-naphthalene)-3H-naphtho[2,1-b]pyrans at ambient temperature. The fading speed of colored forms increase significantly when the electron-donating groups are attached to the para-position of aryl moieties at the 3-position. Further investigations find that (1) a strong electron-donating group is better than a weak electron-donating group for a fast fading speed, (2) an electron-donating group attached to the para-position of the naphthalene ring is better than one attached to the para-position of a benzene ring, and (3) with electron-donating groups at both para-positions of the naphthalene and benzene rings, the fading speed is dramatically increased in both solution and in the rigid polymer matrix.

  我们已经证明，3-芳基-3-(δ-萘)-3H-萘并[2,1-b]吡喃光致变色系统在环境温度下的光稳定状态下显示出很大的光密度。本文介绍了一种在溶液和刚性聚合物基体中改变这种光致变色系统快速消退速度的策略。研究发现，3-芳基-3-(δ-萘)-3H-萘并[2,1-b]吡喃在常温下的褪色速度主要取决于芳基 3-(δ-萘)-3H-萘并[2,1-b]吡喃 3 位上所附取代基团的性质和位置。在芳基的 3 位对位上连接电子捐赠基团时，有色形式的褪色速度会明显加快。进一步的研究发现：(1) 强电子供能基团比弱电子供能基团更有利于快速褪色；(2) 连接在萘环对位上的电子供能基团比连接在苯环对位上的电子供能基团更有利于快速褪色；(3) 在萘环和苯环的对位上都有电子供能基团时，溶液和刚性聚合物基体中的褪色速度都会显著提高。