1,2-dibromo-4,5-bis{(E)-2-[p-N,N-bis(2-tert-butyldimethylsiloxyethyl)aminophenyl]ethenyl}benzene | 823791-45-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 1,2-dibromo-4,5-bis{(E)-2-[p-N,N-bis(2-tert-butyldimethylsiloxyethyl)aminophenyl]ethenyl}benzene
• CAS: 823791-45-3
• 化学式: C₅₄H₉₀Br₂N₂O₄Si₄
• 分子量: 1103.47
• InChiKey: GACSXTLYEDGHGG-GPAWKIAZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  17.25
• 重原子数：
  66.0
• 可旋转键数：
  22.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  43.4
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  1,2-dibromo-4,5-bis{(E)-2-[p-N,N-bis(2-tert-butyldimethylsiloxyethyl)aminophenyl]ethenyl}benzene 在 palladium diacetate 、 三乙胺 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 72.17h， 生成
  参考文献：
  名称：

  Self-Assembled Electrooptic Thin Films with Remarkably Blue-Shifted Optical Absorption Based on an X-Shaped Chromophore

  摘要：

  An "X-shaped" two-dimensional electrooptic (EO) chromophore with extended orthogonal conjugation was designed and synthesized. Self-assembled thin films of this chromophore were fabricated via layer-by-layer chemisorptive siloxane-based self-assembly. The films exhibit a dramatically blue-shifted optical maximum (325 nm) while maintaining a large EO response (chi33(2) approximately 232 pm/V at 1064 nm; r33 approximately 43 pm/V at 1550 nm).

  DOI：

  10.1021/ja045043k
• 作为产物：
  描述：

  p-bis(2-tert-butyldimethylsiloxyethyl)aminobenzaldehyde 、 [(4,5-dibromo-1,2-phenylene)bis(methylene)]bisphosphonic acid tetraethyl ester 在 sodium methylate 作用下， 以 四氢呋喃 为溶剂， 反应 11.0h， 以53.8%的产率得到1,2-dibromo-4,5-bis{(E)-2-[p-N,N-bis(2-tert-butyldimethylsiloxyethyl)aminophenyl]ethenyl}benzene
  参考文献：
  名称：

  Self-Assembled Electrooptic Thin Films with Remarkably Blue-Shifted Optical Absorption Based on an X-Shaped Chromophore

  摘要：

  An "X-shaped" two-dimensional electrooptic (EO) chromophore with extended orthogonal conjugation was designed and synthesized. Self-assembled thin films of this chromophore were fabricated via layer-by-layer chemisorptive siloxane-based self-assembly. The films exhibit a dramatically blue-shifted optical maximum (325 nm) while maintaining a large EO response (chi33(2) approximately 232 pm/V at 1064 nm; r33 approximately 43 pm/V at 1550 nm).

  DOI：

  10.1021/ja045043k

文献信息

• X-Shaped Electro-optic Chromophore with Remarkably Blue-Shifted Optical Absorption. Synthesis, Characterization, Linear/Nonlinear Optical Properties, Self-Assembly, and Thin Film Microstructural Characteristics
  作者：Hu Kang、Guennadi Evmenenko、Pulak Dutta、Koen Clays、Kai Song、Tobin J. Marks

  DOI：10.1021/ja060185v

  日期：2006.5.1

  A novel type of "X-shaped" two-dimensional electro-optic (EO) chromophore with extended conjugation has been synthesized and characterized. This chromophore is found to exhibit a remarkably blue-shifted optical maximum (357 nm in CH2Cl2) while maintaining a very large first hyperpolarizability (beta). Hyper-Rayleigh Scattering (HRS) measurements at 800 nm provide a beta(zzz) value of 1840 x 10(-30) esu. Self-assembled thin films of this chromophore were fabricated via a layer-by-layer chemisorptive siloxane-based approach. The chromophoric multilayers have been characterized by transmission optical spectroscopy, advancing contact angle measurements, synchrotron X-ray reflectivity, atomic force microscopy, and angle-dependent polarized second harmonic generation spectroscopy. The self-assembled chromophoric films exhibit a dramatically blue-shifted optical maximum ( 325 nm) while maintaining a large EO response (chi((2))(333) similar to 232 pm/V at 1064 nm; r(33) similar to 45 pm/V at 1310 nm). This work demonstrates an attractive approach to developing EO materials offering improved nonlinearity-transparency trade-offs.