10-(4-methoxyphenyl)-5,10-diphenylbenzo-[de]pyrano[2,3-g]isoquinoline-4,6(5H,10H)-dione | 1267600-38-3

• 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: 10-(4-methoxyphenyl)-5,10-diphenylbenzo-[de]pyrano[2,3-g]isoquinoline-4,6(5H,10H)-dione
• 英文别名: 4-(4-Methoxyphenyl)-4,11-diphenyl-3-oxa-11-azatetracyclo[7.7.1.02,7.013,17]heptadeca-1,5,7,9(17),13,15-hexaene-10,12-dione；4-(4-methoxyphenyl)-4,11-diphenyl-3-oxa-11-azatetracyclo[7.7.1.02,7.013,17]heptadeca-1,5,7,9(17),13,15-hexaene-10,12-dione
• CAS: 1267600-38-3
• 化学式: C₃₄H₂₃NO₄
• 分子量: 509.561
• InChiKey: JRFGUXCAXOCSDD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  39
• 可旋转键数：
  4
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  10-(4-methoxyphenyl)-5,10-diphenylbenzo-[de]pyrano[2,3-g]isoquinoline-4,6(5H,10H)-dione 以 乙腈 为溶剂， 生成 、
  参考文献：
  名称：

  Synthesis and Photochromism of Naphthopyrans Bearing Naphthalimide Chromophore: Predominant Thermal Reversibility in Color-Fading and Fluorescence Switch

  摘要：

  Two novel photochromic naphthopyrans containing naphthalimide moieties (Nip1 and Nip2) were studied in solution under flash photolysis conditions, exhibiting highly photochromic response, rapid thermal bleaching rate and good fatigue-resistance. Owing to the different N-substituted imide groups at the naphthalimide units, the thermal bleaching rate of Nip2 bearing phenyl on the naphthalimide unit is found to be approximately 2 times that of Nip1 bearing n-butyl, indicating that the photochromic properties can be modulated with introduction of different functional groups on the naphthalimide unit. In Nip1 and Nip2, the strong electron-withdrawing effect of the imide group incorporated at the naphthalimide moiety maintains several merits: (i) shifting absorption bands to longer wavelength, (ii) beneficial to an enhancement in the ratio of transoid-cis (TC) isomer and an increase in the transformation rate from transoid-trans (TT) to TC with respect to reference compound NP, and (iii) resulting in a preferable color bleaching rate and fading absolutely to their colorless state with thermal reversibility. As demonstrated in the system of NP, the slow transformation process from TT to TC might be the predominant dynamic step in thermal back process, leading to the residual color of NP being only faded to its original colorless state by visible light irradiation. The optical densities of colored forms for Nip1 and Nip2 are dependent upon the intensity of incident light, ensuring a possible application in the manufacture of ophthalmic lenses and smart windows. Moreover, the fluorescence of Nip1 and Nip2 can be switched on and off by photoinduced conversion between the closed and open forms.

  DOI：

  10.1021/jp208082w
• 作为产物：
  描述：

  4-溴-1,8-萘二甲酸酐 在 aluminum oxide 、 氢碘酸 、 copper(II) sulfate 、 溶剂黄146 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 61.0h， 生成 10-(4-methoxyphenyl)-5,10-diphenylbenzo-[de]pyrano[2,3-g]isoquinoline-4,6(5H,10H)-dione
  参考文献：
  名称：

  Synthesis and Photochromism of Naphthopyrans Bearing Naphthalimide Chromophore: Predominant Thermal Reversibility in Color-Fading and Fluorescence Switch

  摘要：

  Two novel photochromic naphthopyrans containing naphthalimide moieties (Nip1 and Nip2) were studied in solution under flash photolysis conditions, exhibiting highly photochromic response, rapid thermal bleaching rate and good fatigue-resistance. Owing to the different N-substituted imide groups at the naphthalimide units, the thermal bleaching rate of Nip2 bearing phenyl on the naphthalimide unit is found to be approximately 2 times that of Nip1 bearing n-butyl, indicating that the photochromic properties can be modulated with introduction of different functional groups on the naphthalimide unit. In Nip1 and Nip2, the strong electron-withdrawing effect of the imide group incorporated at the naphthalimide moiety maintains several merits: (i) shifting absorption bands to longer wavelength, (ii) beneficial to an enhancement in the ratio of transoid-cis (TC) isomer and an increase in the transformation rate from transoid-trans (TT) to TC with respect to reference compound NP, and (iii) resulting in a preferable color bleaching rate and fading absolutely to their colorless state with thermal reversibility. As demonstrated in the system of NP, the slow transformation process from TT to TC might be the predominant dynamic step in thermal back process, leading to the residual color of NP being only faded to its original colorless state by visible light irradiation. The optical densities of colored forms for Nip1 and Nip2 are dependent upon the intensity of incident light, ensuring a possible application in the manufacture of ophthalmic lenses and smart windows. Moreover, the fluorescence of Nip1 and Nip2 can be switched on and off by photoinduced conversion between the closed and open forms.

  DOI：

  10.1021/jp208082w

文献信息

• Synthesis and Photochromism of Naphthopyrans Bearing Naphthalimide Chromophore: Predominant Thermal Reversibility in Color-Fading and Fluorescence Switch
  作者：Liwen Song、Yuheng Yang、Qiong Zhang、He Tian、Weihong Zhu

  DOI：10.1021/jp208082w

  日期：2011.12.15

  Two novel photochromic naphthopyrans containing naphthalimide moieties (Nip1 and Nip2) were studied in solution under flash photolysis conditions, exhibiting highly photochromic response, rapid thermal bleaching rate and good fatigue-resistance. Owing to the different N-substituted imide groups at the naphthalimide units, the thermal bleaching rate of Nip2 bearing phenyl on the naphthalimide unit is found to be approximately 2 times that of Nip1 bearing n-butyl, indicating that the photochromic properties can be modulated with introduction of different functional groups on the naphthalimide unit. In Nip1 and Nip2, the strong electron-withdrawing effect of the imide group incorporated at the naphthalimide moiety maintains several merits: (i) shifting absorption bands to longer wavelength, (ii) beneficial to an enhancement in the ratio of transoid-cis (TC) isomer and an increase in the transformation rate from transoid-trans (TT) to TC with respect to reference compound NP, and (iii) resulting in a preferable color bleaching rate and fading absolutely to their colorless state with thermal reversibility. As demonstrated in the system of NP, the slow transformation process from TT to TC might be the predominant dynamic step in thermal back process, leading to the residual color of NP being only faded to its original colorless state by visible light irradiation. The optical densities of colored forms for Nip1 and Nip2 are dependent upon the intensity of incident light, ensuring a possible application in the manufacture of ophthalmic lenses and smart windows. Moreover, the fluorescence of Nip1 and Nip2 can be switched on and off by photoinduced conversion between the closed and open forms.