6-nitronaphthalene-2,3-dicarboxylic acid | 139451-35-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 6-nitronaphthalene-2,3-dicarboxylic acid
• 英文别名: 6-nitro-2,3-naphthalenedicarboxylic acid
• CAS: 139451-35-7
• 化学式: C₁₂H₇NO₆
• 分子量: 261.191
• InChiKey: LKNDVXGJPYFZLS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  120
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  6-nitronaphthalene-2,3-dicarboxylic acid 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 4.0h， 以85%的产率得到6-amino-2,3-naphthalenedicarboxylic acid
  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-nitrobenzo[f][2]benzofuran-1,3-dione 在 水 、 sodium hydroxide 作用下， 以9.72 g的产率得到6-nitronaphthalene-2,3-dicarboxylic acid
  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

文献信息

• Investigation of a sensing approach based on a rapid reduction of azide to selectively measure bioavailability of H₂S
  作者：Gunwoo Kim、Eunju Jang、Alexis M. Page、Ting Ding、Kimberly A. Carlson、Haishi Cao

  DOI：10.1039/c6ra20478c

  日期：——

  An azide appended 2,3-naphtahlimide (AHS) is functionalized as a fluorescence approach for quantitative detection of H₂S in the range of 0–100 μM. In the presence of H₂S, AHS displayed a 17-fold fluorescence enhancement that showed a highly linear correlation with H₂S level.

  一种带有偶氮基团的2,3-萘酰亚胺（AHS）被功能化为一种荧光方法，用于定量检测0-100μM范围内的H2S。在存在 的情况下，AHS显示出17倍的荧光增强，与 水平呈高度线性相关。