1-((4-bromophenoxy)methyl)-4-(5,5''-dihexyl-[2,2':3',2'']terthiophene-5'-yl)benzene | 1119745-78-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-((4-bromophenoxy)methyl)-4-(5,5''-dihexyl-[2,2':3',2'']terthiophene-5'-yl)benzene
• CAS: 1119745-78-6
• 化学式: C₃₇H₄₂OS₃
• 分子量: 598.938
• InChiKey: OKRAYLWPLZYNED-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.7
• 重原子数：
  41.0
• 可旋转键数：
  16.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  9.23
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1-((4-bromophenoxy)methyl)-4-(5,5''-dihexyl-[2,2':3',2'']terthiophene-5'-yl)benzene 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 48.0h， 以50%的产率得到4-(4,5-bis(5-hexylthiophen-2-yl)thiophen-2-yl)phenol
  参考文献：
  名称：

  Highly Sensitive and Selective “Turn-on” Calcium Cation Sensing from a Dendronic Terthiophene Tetraethylene Glycol (TEG) Molecule

  摘要：

  A molecule consisting of a branched or dendronic terthiophene with tetraethylene glycol moiety (3T5O) was synthesized for highly sensitive and selective calcium ion detection in solution. The sulfur atoms of the terthiophene dendron moiety contribute to the metal-ligand complexation of calcium cations. The modification of the terthiophene dendrons with a hydroxyl-terminated tetracthylene glycol (TEG) group produces a twisted intramolecular charge transfer (TICT) event in which the terthiophene moiety is conformationally twisted, affecting its chromophoric and fluorophoric activity. This twisted conformation resulted in an increase Ill emission intensity at 320 nm, at the same time producing a blue shift in the absorption spectra. This process enabled a "turn-on" system for calcium ion detection compared to most "turn-off" systems involving a quenching route. The intensity of the emission is related to saturation of the terthiophene moiety at a concentration of 3T5O:[Ca2+] 1:4, of similar to 1 x 10(-8) M, which indicates high sensitivity for calcium cations. No response with other cations such as Nal(+), K+, and Mg2+ was observed, which also indicates high selectivity for the system. Conformational analysis of the 3T5O and the twisted terthiophene dendron geometry was done by semiempirical PM3 modeling. In an effort to distinguish specific interactions between monovalent and divalent cations and the 3T5O, restricted Hartree-Fock level calculations using the STO-3G basis set were also performed. The calculations correlated with the experimental results.

  DOI：

  10.1021/jp1068522
• 作为产物：
  描述：

  4-苄氧基溴苯 、 tributyl(5,5''-dihexyl-[2,2';3',2'']terthiophen-5'-yl)stannane 在 copper(l) iodide 、 四(三苯基膦)钯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以50%的产率得到1-((4-bromophenoxy)methyl)-4-(5,5''-dihexyl-[2,2':3',2'']terthiophene-5'-yl)benzene
  参考文献：
  名称：

  Highly Sensitive and Selective “Turn-on” Calcium Cation Sensing from a Dendronic Terthiophene Tetraethylene Glycol (TEG) Molecule

  摘要：

  A molecule consisting of a branched or dendronic terthiophene with tetraethylene glycol moiety (3T5O) was synthesized for highly sensitive and selective calcium ion detection in solution. The sulfur atoms of the terthiophene dendron moiety contribute to the metal-ligand complexation of calcium cations. The modification of the terthiophene dendrons with a hydroxyl-terminated tetracthylene glycol (TEG) group produces a twisted intramolecular charge transfer (TICT) event in which the terthiophene moiety is conformationally twisted, affecting its chromophoric and fluorophoric activity. This twisted conformation resulted in an increase Ill emission intensity at 320 nm, at the same time producing a blue shift in the absorption spectra. This process enabled a "turn-on" system for calcium ion detection compared to most "turn-off" systems involving a quenching route. The intensity of the emission is related to saturation of the terthiophene moiety at a concentration of 3T5O:[Ca2+] 1:4, of similar to 1 x 10(-8) M, which indicates high sensitivity for calcium cations. No response with other cations such as Nal(+), K+, and Mg2+ was observed, which also indicates high selectivity for the system. Conformational analysis of the 3T5O and the twisted terthiophene dendron geometry was done by semiempirical PM3 modeling. In an effort to distinguish specific interactions between monovalent and divalent cations and the 3T5O, restricted Hartree-Fock level calculations using the STO-3G basis set were also performed. The calculations correlated with the experimental results.

  DOI：

  10.1021/jp1068522