5-[2-(4-{[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-methyl-amino}-phenyl)-vinyl]-3-hydroxymethyl-thiophene-2-carbaldehyde | 1061707-60-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-[2-(4-{[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-methyl-amino}-phenyl)-vinyl]-3-hydroxymethyl-thiophene-2-carbaldehyde
• 英文别名: 5-[(E)-2-[4-[2-[tert-butyl(dimethyl)silyl]oxyethyl-methylamino]phenyl]ethenyl]-3-(hydroxymethyl)thiophene-2-carbaldehyde
• CAS: 1061707-60-5
• 化学式: C₂₃H₃₃NO₃SSi
• 分子量: 431.671
• InChiKey: GMWPMOMNLVRYEH-FMIVXFBMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.68
• 重原子数：
  29
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  78
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-[2-(4-{[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-methyl-amino}-phenyl)-vinyl]-3-hydroxymethyl-thiophene-2-carbaldehyde 、 2-[3-氰基-4-甲基-5-苯基-5-三氟甲基-2(5H)-呋喃亚基]-丙二腈 以 四氢呋喃 、 乙醇 为溶剂， 以60%的产率得到2-[4-(2-{5-[2-(4-{[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-methyl-amino}-phenyl)-vinyl]-3-hydroxymethyl-thiophen-2-yl}-vinyl)-3-cyano-5-phenyl-5-trifluoromethyl-5H-furan-2-ylidene]-malononitrile
  参考文献：
  名称：

  Theory-Guided Design and Synthesis of Multichromophore Dendrimers:  An Analysis of the Electro-optic Effect

  摘要：

  Extensive experimental and theoretical study suggests that interchromophore electrostatic interactions are among the most severe impediments to the induction and stability of large electro-optic coefficients in electric-field-poled organic materials. In this report, multichromophore-containing dendritic materials have been investigated as a means to minimize unwanted attenuation of nonlinear optical (electro-optic) activity at high chromophore loading. The dendritic molecular architectures employed were designed to provide optimized molecular scaffolding for electric-field-induced molecular reorientation. Design parameters were based upon past experimental results in conjunction with statistical and quantum mechanical modeling. The electro-optic behavior of these materials was evaluated through experimental and theoretical analysis. Experimental data collected from the dendrimer structures depict a reasonably linear relationship between chromophore number density (N) and electro-optic activity (r(33)) demonstrating a deviation from the dipolar frustration that typically limits r(33) in conventional chromophore/polymer composite materials. The observed linear dependence holds at higher chromophore densities than those that have been found to be practical in systems of organic NLO chromophores dispersed in polymer hosts. Theoretical analysis of these results using Monte Carlo modeling reproduces the experimentally observed trends confirming linear dependence of electro-optic activity on N in the dendrimer materials. These results provide new insight into the ordering behavior of EO dendrimers and demonstrate that the frequently observed asymptotic dependence of electro-optic activity on chromophore number density may be overcome through rational design.

  DOI：

  10.1021/ja068322b
• 作为产物：
  描述：

  (4-溴-2-噻吩基)甲醇 在 盐酸 、 sodium hydroxide 、 sodium tetrahydroborate 、 正丁基锂 、 potassium tert-butylate 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 正己烷 为溶剂， 反应 53.09h， 生成 5-[2-(4-{[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-methyl-amino}-phenyl)-vinyl]-3-hydroxymethyl-thiophene-2-carbaldehyde
  参考文献：
  名称：

  Theory-Guided Design and Synthesis of Multichromophore Dendrimers:  An Analysis of the Electro-optic Effect

  摘要：

  Extensive experimental and theoretical study suggests that interchromophore electrostatic interactions are among the most severe impediments to the induction and stability of large electro-optic coefficients in electric-field-poled organic materials. In this report, multichromophore-containing dendritic materials have been investigated as a means to minimize unwanted attenuation of nonlinear optical (electro-optic) activity at high chromophore loading. The dendritic molecular architectures employed were designed to provide optimized molecular scaffolding for electric-field-induced molecular reorientation. Design parameters were based upon past experimental results in conjunction with statistical and quantum mechanical modeling. The electro-optic behavior of these materials was evaluated through experimental and theoretical analysis. Experimental data collected from the dendrimer structures depict a reasonably linear relationship between chromophore number density (N) and electro-optic activity (r(33)) demonstrating a deviation from the dipolar frustration that typically limits r(33) in conventional chromophore/polymer composite materials. The observed linear dependence holds at higher chromophore densities than those that have been found to be practical in systems of organic NLO chromophores dispersed in polymer hosts. Theoretical analysis of these results using Monte Carlo modeling reproduces the experimentally observed trends confirming linear dependence of electro-optic activity on N in the dendrimer materials. These results provide new insight into the ordering behavior of EO dendrimers and demonstrate that the frequently observed asymptotic dependence of electro-optic activity on chromophore number density may be overcome through rational design.

  DOI：

  10.1021/ja068322b

文献信息

• Theory-Guided Design and Synthesis of Multichromophore Dendrimers:  An Analysis of the Electro-optic Effect
  作者：Philip A. Sullivan、Harrison Rommel、Yi Liao、Benjamin C. Olbricht、Andrew J. P. Akelaitis、Kimberly A. Firestone、Jae-Wook Kang、Jingdong Luo、Joshua A. Davies、Dong Hoon Choi、Bruce E. Eichinger、Philip J. Reid、Antao Chen、Alex K-Y. Jen、Bruce H. Robinson、Larry R. Dalton

  DOI：10.1021/ja068322b

  日期：2007.6.1

  Extensive experimental and theoretical study suggests that interchromophore electrostatic interactions are among the most severe impediments to the induction and stability of large electro-optic coefficients in electric-field-poled organic materials. In this report, multichromophore-containing dendritic materials have been investigated as a means to minimize unwanted attenuation of nonlinear optical (electro-optic) activity at high chromophore loading. The dendritic molecular architectures employed were designed to provide optimized molecular scaffolding for electric-field-induced molecular reorientation. Design parameters were based upon past experimental results in conjunction with statistical and quantum mechanical modeling. The electro-optic behavior of these materials was evaluated through experimental and theoretical analysis. Experimental data collected from the dendrimer structures depict a reasonably linear relationship between chromophore number density (N) and electro-optic activity (r(33)) demonstrating a deviation from the dipolar frustration that typically limits r(33) in conventional chromophore/polymer composite materials. The observed linear dependence holds at higher chromophore densities than those that have been found to be practical in systems of organic NLO chromophores dispersed in polymer hosts. Theoretical analysis of these results using Monte Carlo modeling reproduces the experimentally observed trends confirming linear dependence of electro-optic activity on N in the dendrimer materials. These results provide new insight into the ordering behavior of EO dendrimers and demonstrate that the frequently observed asymptotic dependence of electro-optic activity on chromophore number density may be overcome through rational design.