1,8-bis(4-amidinophenyl)naphthalene | 1610972-92-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: 1,8-bis(4-amidinophenyl)naphthalene
• 英文别名: 4-[8-(4-Carbamimidoylphenyl)naphthalen-1-yl]benzenecarboximidamide；4-[8-(4-carbamimidoylphenyl)naphthalen-1-yl]benzenecarboximidamide
• CAS: 1610972-92-3
• 化学式: C₂₄H₂₀N₄
• 分子量: 364.45
• InChiKey: HRMRMIDRFHBZIY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  99.7
• 氢给体数：
  4
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  壬二酸 、 1,8-bis(4-amidinophenyl)naphthalene 以 二甲基亚砜 为溶剂， 生成 4,4'-(naphthalene-1,8-diyl)dibenzimidamide nonanedioate
  参考文献：
  名称：

  Fluorescent detection of amidinium-carboxylate and amidinium formation using a 1,8-diphenylnaphthalene-based diamidine: dicarboxylic acid recognition with high fluorescence efficiency

  摘要：

  A 1,8-diphenyinaphthalene-based diamidine (1) 'turn-on' fluorescent probe for the detection of dicarboxylic acids has been designed and synthesized. The fluorescence spectra of the diamidine 1 with carboxylic acids that showed two different fluorescence bands, which corresponded to the amidinium-carboxylate (lambda(em)=410-430 nm) and amidinium (lambda(em)=440-470 nm as a broad band, which consisted from two peaks) formation, were confirmed by DOSY NMR and TD-DFT calculations. The complexation of diamidine 1 with dicarboxylic acids, which have sufficient distances between the two carboxylic groups for binding to the diamidine 1 (dicarboxylic acids 3, 4, and alpha,omega-dicarboxylic acids 6 (C-6-C-20)), showed the formation of 1:1 complexes (i.e., amidinium-carboxylate formation). On the other hand, for the complexation with monocarboxylic acids and dicarboxylic acids having insufficient distances between the two carboxylic groups (benzoic acid 5, acetic acid 7, and alpha,omega-dicarboxylic acids 6 (C-3-C-5)), formation of the amidinium (1.2H(+)) was observed. Relatively similar binding constants (10(-5)) for the complexation of the diamidine 1 with dicarboxylic acids 6, which depend on their chain length (strain), were observed due to the flexibility of the 1,8-diphenylnaphthalene unit. Additionally, for the complexation of the diamidine 1 with dicarboxylic acids, higher fluorescence quantum yields (Phi(fl): up to 80%) were observed when compared to the binding of the diamidine 2 (Phi(fl): up to 35%). (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.03.036
• 作为产物：
  描述：

  1,8-二碘萘 在 盐酸 、 四(三苯基膦)钯 、 水 、 三甲基铝 、 sodium carbonate 、 氯化铵 、 sodium hydroxide 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 水 、 甲苯 为溶剂， 反应 42.08h， 生成 1,8-bis(4-amidinophenyl)naphthalene
  参考文献：
  名称：

  Fluorescent detection of amidinium-carboxylate and amidinium formation using a 1,8-diphenylnaphthalene-based diamidine: dicarboxylic acid recognition with high fluorescence efficiency

  摘要：

  A 1,8-diphenyinaphthalene-based diamidine (1) 'turn-on' fluorescent probe for the detection of dicarboxylic acids has been designed and synthesized. The fluorescence spectra of the diamidine 1 with carboxylic acids that showed two different fluorescence bands, which corresponded to the amidinium-carboxylate (lambda(em)=410-430 nm) and amidinium (lambda(em)=440-470 nm as a broad band, which consisted from two peaks) formation, were confirmed by DOSY NMR and TD-DFT calculations. The complexation of diamidine 1 with dicarboxylic acids, which have sufficient distances between the two carboxylic groups for binding to the diamidine 1 (dicarboxylic acids 3, 4, and alpha,omega-dicarboxylic acids 6 (C-6-C-20)), showed the formation of 1:1 complexes (i.e., amidinium-carboxylate formation). On the other hand, for the complexation with monocarboxylic acids and dicarboxylic acids having insufficient distances between the two carboxylic groups (benzoic acid 5, acetic acid 7, and alpha,omega-dicarboxylic acids 6 (C-3-C-5)), formation of the amidinium (1.2H(+)) was observed. Relatively similar binding constants (10(-5)) for the complexation of the diamidine 1 with dicarboxylic acids 6, which depend on their chain length (strain), were observed due to the flexibility of the 1,8-diphenylnaphthalene unit. Additionally, for the complexation of the diamidine 1 with dicarboxylic acids, higher fluorescence quantum yields (Phi(fl): up to 80%) were observed when compared to the binding of the diamidine 2 (Phi(fl): up to 35%). (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.03.036