6-iodo-2,3-naphthalenedicarboxylic anhydride | 1243151-49-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并呋喃类
• 英文名称: 6-iodo-2,3-naphthalenedicarboxylic anhydride
• CAS: 1243151-49-6
• 化学式: C₁₂H₅IO₃
• 分子量: 324.074
• InChiKey: OBZUJPHKVCWNLJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.76
• 重原子数：
  16.0
• 可旋转键数：
  0.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  6-iodo-2,3-naphthalenedicarboxylic anhydride 在 尿素 作用下， 反应 2.0h， 以95%的产率得到6-iodo-1H-benzo[f]isoindole-1,3(2H)-dione
  参考文献：
  名称：

  Unusual large Stokes shift and solvatochromic fluorophore: Synthesis, spectra, and solvent effect of 6-substituted 2,3-naphthalimide

  摘要：

  In this article four new series of 6-substituted 2 3-naphthalimides (1a-d 2a-d 3a-d 4a-d and 4 e-h) have been designed and synthesized through the formation of key cyclic anhydride intermediate which was the precursor of the well known environment-sensitive fluorophore [6-N,N-dimethylammonaphthalimides (6-DMN)] and other 6-substituted 2 3-naphthalimide series (2 3 4) Based on 6-amino-2 3-naphthalimide (6-ANP) compound a new type of fluorophore was found to exhibit moderate to unusual large Stokes shift (297-303 nm) 6-ANP derivatives display relatively low fluorescence quantum yields in high polar protic solvents such as water (Phi(F) similar to 0 004 571-576 nm) and a significant unusual red shift due to (1) hydrogen bonding interaction of the excited state of the molecule with the solvents which presumably enhance the intersystem crossing process in the system to quench fluorescence (2) this large Stokes shift was assumed to be the consequence of a substantial change of the geometric structure from the ground state (S-0) to the first excited state (S-1)) Compared with the other compounds studied the fluorescence of the nitro- and halo-derivatives was rather weak probably due to the efficient intersystem crossing leading to a non-reactive triplet state (C) 2010 Elsevier B V All rights reserved

  DOI：

  10.1016/j.jphotochem.2010.09.002
• 作为产物：
  描述：

  6-Iodonaphthalene-2,3-dicarboxylic acid 在 乙酸酐 作用下， 反应 0.25h， 生成 6-iodo-2,3-naphthalenedicarboxylic anhydride
  参考文献：
  名称：

  Unusual large Stokes shift and solvatochromic fluorophore: Synthesis, spectra, and solvent effect of 6-substituted 2,3-naphthalimide

  摘要：

  In this article four new series of 6-substituted 2 3-naphthalimides (1a-d 2a-d 3a-d 4a-d and 4 e-h) have been designed and synthesized through the formation of key cyclic anhydride intermediate which was the precursor of the well known environment-sensitive fluorophore [6-N,N-dimethylammonaphthalimides (6-DMN)] and other 6-substituted 2 3-naphthalimide series (2 3 4) Based on 6-amino-2 3-naphthalimide (6-ANP) compound a new type of fluorophore was found to exhibit moderate to unusual large Stokes shift (297-303 nm) 6-ANP derivatives display relatively low fluorescence quantum yields in high polar protic solvents such as water (Phi(F) similar to 0 004 571-576 nm) and a significant unusual red shift due to (1) hydrogen bonding interaction of the excited state of the molecule with the solvents which presumably enhance the intersystem crossing process in the system to quench fluorescence (2) this large Stokes shift was assumed to be the consequence of a substantial change of the geometric structure from the ground state (S-0) to the first excited state (S-1)) Compared with the other compounds studied the fluorescence of the nitro- and halo-derivatives was rather weak probably due to the efficient intersystem crossing leading to a non-reactive triplet state (C) 2010 Elsevier B V All rights reserved

  DOI：

  10.1016/j.jphotochem.2010.09.002