4-diphenylamino-1,8-naphthalene anhydride | 78153-38-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 4-diphenylamino-1,8-naphthalene anhydride
• 英文别名: 4-diphenylaminonaphthalic anhydride；8-(N-phenylanilino)-3-oxatricyclo[7.3.1.05,13]trideca-1(12),5(13),6,8,10-pentaene-2,4-dione
• CAS: 78153-38-5
• 化学式: C₂₄H₁₅NO₃
• 分子量: 365.388
• InChiKey: SEZCMHFCSSZDDY-UHFFFAOYSA-N

物化性质

• 熔点：
  304-305 °C(Solv: 1,2-dichloroethane (107-06-2))
• 沸点：
  595.4±33.0 °C(Predicted)
• 密度：
  1.364±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.62
• 重原子数：
  28.0
• 可旋转键数：
  3.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  46.61
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  4-氯-1,8-萘二甲酸酐 、 二苯胺 在 copper (I) acetate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 30.0h， 以32%的产率得到4-diphenylamino-1,8-naphthalene anhydride
  参考文献：
  名称：

  Krasovitskii, B. M.; Shevchenko, E. A.; Distanov, V. B., Journal of Organic Chemistry USSR (English Translation), 1983, vol. 19, # 6, p. 1165 - 1168

  摘要：

  DOI：

文献信息

• “Push–pull” 1,8-naphthalic anhydride with multiple triphenylamine groups as electron donor
  作者：Limin Wang、Yan Shi、Yingyuan Zhao、Heyuan Liu、Xiyou Li、Ming Bai

  DOI：10.1016/j.molstruc.2013.10.004

  日期：2014.1

  In this paper, the "push-pull" molecules consisting of different number of triphenylamino groups and 1,8-naphthalic anhydride ring were designed and synthesized. The UV-vis absorption and emission spectra of these compounds were recorded. Along with the increase on the number of the electron donating triphenylamino groups, both the absorption and emission bands show significant red shift. More importantly, the fluorescence quantum yields drop sharply along with the increase on the number of triphenylamino groups. The molecular structure, the frontier molecular orbital energies and the energy gaps between the highest occupied molecular orbital (HOMO) and the lowest un-occupied molecular orbital (LUMO) were calculated with OFT method. The calculated results indicate that the connection of more electron donating triphenylamino groups in molecule caused a change for the first excited state from an intramolecular charge transfer (ICT) state to an intramolecular electron transfer state (ET). This change on the first excited state has led to the fluorescence quenching. (C) 2013 Elsevier B.V. All rights reserved.
• KRASOVITSKIJ, B. M.;SHEVCHENKO, EH. A.;DISTANOV, V. B., ZH. ORGAN. XIMII, 1983, 19, N 6, 1305-1308
  作者：KRASOVITSKIJ, B. M.、SHEVCHENKO, EH. A.、DISTANOV, V. B.

  DOI：——

  日期：——