8,8'-bis(3-butylthioureidomethyl)-2,2'-binaphthalene

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 8,8'-bis(3-butylthioureidomethyl)-2,2'-binaphthalene
• 英文别名: 8,8'-Bis(3-butylthioureidomethyl)-2,2'-binaphthalene；1-butyl-3-[[7-[8-[(butylcarbamothioylamino)methyl]naphthalen-2-yl]naphthalen-1-yl]methyl]thiourea
• 化学式: C₃₂H₃₈N₄S₂
• 分子量: 542.813
• InChiKey: ALJIOEKRHKHNER-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  38
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  112
• 氢给体数：
  4
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  8,8'-bis(bromomethyl)-2,2'-binaphthalene 在 palladium on activated charcoal sodium azide 、 氢气 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 52.0h， 生成 8,8'-bis(3-butylthioureidomethyl)-2,2'-binaphthalene
  参考文献：
  名称：

  UV–vis and fluorescence spectroscopic detection of anions by the conformational restriction of 2,2′-binaphthalene derivatives bearing thiourea groups through a methylene spacer

  摘要：

  Novel fluorescence receptors, 2 and 3 based on 2,2'-binaphthalene possessing thiourea moieties via a methylene spacer have been synthesized. Hydrogen bonds of NH groups of thiourea moieties with acetate anion were confirmed by H-1 NMR study in MeCN-d(3). These receptors showed characteristic UV-vis spectral changes through isosbestic points on complexation with anions inspite of lacking conjugation between the chromophore and the binding sites in polar organic solvent such as acetonitfile. The UV-vis spectral changes arise from the conformational restriction of the 2,2'-binaphthyl skeleton on the complexation. The receptors exhibit high selectivities for AcO- and F-. The fluorescence intensity of the receptors decreases with the increasing amount of the AcO-, however, addition of F- induces a different change in its fluorescence spectrum, in which shorter emission of the receptors decreases with the increase in F- concentration, while the longer emission of the receptors increases through an isoemissive point in MeCN. The results suggest that favorable dual-wavelength ratiometric fluorescence measurement can be conducted by the receptors for F-. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.03.002

文献信息

• UV–vis and fluorescence spectroscopic detection of anions by the conformational restriction of 2,2′-binaphthalene derivatives bearing thiourea groups through a methylene spacer
  作者：Shin-ichi Kondo、Masakazu Sato

  DOI：10.1016/j.tet.2006.03.002

  日期：2006.5

  Novel fluorescence receptors, 2 and 3 based on 2,2'-binaphthalene possessing thiourea moieties via a methylene spacer have been synthesized. Hydrogen bonds of NH groups of thiourea moieties with acetate anion were confirmed by H-1 NMR study in MeCN-d(3). These receptors showed characteristic UV-vis spectral changes through isosbestic points on complexation with anions inspite of lacking conjugation between the chromophore and the binding sites in polar organic solvent such as acetonitfile. The UV-vis spectral changes arise from the conformational restriction of the 2,2'-binaphthyl skeleton on the complexation. The receptors exhibit high selectivities for AcO- and F-. The fluorescence intensity of the receptors decreases with the increasing amount of the AcO-, however, addition of F- induces a different change in its fluorescence spectrum, in which shorter emission of the receptors decreases with the increase in F- concentration, while the longer emission of the receptors increases through an isoemissive point in MeCN. The results suggest that favorable dual-wavelength ratiometric fluorescence measurement can be conducted by the receptors for F-. (c) 2006 Elsevier Ltd. All rights reserved.