N,N-bis(4-n-butylphenyl)aniline | 230623-67-3

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N,N-bis(4-n-butylphenyl)aniline
• 英文别名: N,N-bis(4-butylphenyl)-3-methoxyaniline
• CAS: 230623-67-3
• 化学式: C₂₇H₃₃NO
• 分子量: 387.565
• InChiKey: HFLFLXXKPCZUIP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.9
• 重原子数：
  29
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N,N-bis(4-n-butylphenyl)aniline 在 sodium ethanolate 、 三溴化硼 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 8.0h， 生成 3-[5-[tert-butyl(dimethyl)silyl]oxypentoxy]-N,N-bis(4-butylphenyl)-4-[2-(4-hexylthiophen-2-yl)ethenyl]aniline
  参考文献：
  名称：

  Synthesis of Functionalized Organic Second-Order Nonlinear Optical Chromophores for Electrooptic Applications

  摘要：

  The design and syntheses of functionalized second-order nonlinear optical chromophores, suitable for covalent incorporation into functionalized high-performance polymers, are described. The chromophores with hydroxy alkyl functionality have diarylamino groups as the donor moiety and a styryl thiophene moiety as the conjugated bridge. The triarylamine parts of the molecules were synthesized using palladium-catalyzed C-N bond forming reactions. The conjugated bridge was assembled using the Wittig reaction. The acceptor groups were installed in the last steps of the syntheses.

  DOI：

  10.1021/jo981707v
• 作为产物：
  描述：

  对丁基溴苯 、 间氨基苯甲醚 在 1,1'-双(二苯基膦)二茂铁 、 tris(dibenzylideneacetone)dipalladium (0) 、 sodium t-butanolate 作用下， 生成 N,N-bis(4-n-butylphenyl)aniline
  参考文献：
  名称：

  Synthesis of Functionalized Organic Second-Order Nonlinear Optical Chromophores for Electrooptic Applications

  摘要：

  The design and syntheses of functionalized second-order nonlinear optical chromophores, suitable for covalent incorporation into functionalized high-performance polymers, are described. The chromophores with hydroxy alkyl functionality have diarylamino groups as the donor moiety and a styryl thiophene moiety as the conjugated bridge. The triarylamine parts of the molecules were synthesized using palladium-catalyzed C-N bond forming reactions. The conjugated bridge was assembled using the Wittig reaction. The acceptor groups were installed in the last steps of the syntheses.

  DOI：

  10.1021/jo981707v

文献信息

• Characterisation of a dipolar chromophore with third-harmonic generation applications in the near-IR
  作者：Yulia A. Getmanenko、Joel M. Hales、Mihaela Balu、Jie Fu、Egbert Zojer、Ohyun Kwon、Jeffrey Mendez、S. Thayumanavan、Gregory Walker、Qing Zhang、Scott D. Bunge、Jean-Luc Brédas、David J. Hagan、Eric W. Van Stryland、Stephen Barlow、Seth R. Marder

  DOI：10.1039/c2jm15599k

  日期：——

  E-2-Tricyanovinyl-3-n-hexyl-5-[4-bis(4-n-butylphenyl)amino}-2-methoxystyryl]-thiophene, 1, has previously been used to demonstrate applications relying on frequency tripling of 1.55 μm light. Here we report the synthesis and chemical characterisation of 1, along with quantum-chemical calculations and additional experimental investigations of its third-order nonlinear properties that give more insight into its frequency tripling properties. Although 1 can be processed into amorphous films, crystals can also be grown by slow evaporation of solutions; the crystal structure determined by X-ray diffraction shows evidence of significant contributions from zwitterionic resonance forms to the ground-state structure, and reveals centrosymmetric packing exhibiting π–π and C–H⋯NC interactions. Both solutions and films of 1 exhibit near-infrared two-photon absorption into the low-lying one-photon-allowed state with a peak two-photon cross-section of ca. 290 GM (measured using the white-light continuum method with a pump wavelength of 1800 nm) at a transition energy equivalent to degenerate two-photon absorption at ca. 1360 nm; two related chromophores are also found to show comparable near-IR two-photon cross-sections. Closed-aperture Z-scan measurements and quantum-chemical calculations indicate that the nonlinear refractive index and third-harmonic generation properties of 1 are strongly dependent on frequency in the telecommunications range, due the aforementioned two-photon resonance.

  E-2-三氰基乙烯基-3-正己基-5-[4-双（4-正丁基苯基）氨基}-2-甲氧基苯乙烯基]-噻吩 1 以前曾被用于演示 1.55 μm 光的频率倍增应用。在此，我们报告了 1 的合成和化学特性，同时还对其三阶非线性特性进行了量子化学计算和额外的实验研究，从而对其频率三倍特性有了更深入的了解。虽然 1 可以加工成无定形薄膜，但也可以通过缓慢蒸发溶液来生长晶体；通过 X 射线衍射确定的晶体结构显示，齐聚共振形式对基态结构有重大贡献，并揭示了呈现 π-π 和 C-H⋯NC 相互作用的中心对称堆积。1 的溶液和薄膜都显示出进入低洼单光子允许态的近红外双光子吸收，其峰值双光子截面约为 290 GM（使用白光连续法测量，泵浦波长为 1800 nm），过渡能量相当于约 1360 nm 处的退化双光子吸收。两种相关的发色团也显示出相似的近红外双光子截面。封闭孔径 Z 扫描测量和量子化学计算表明，由于上述双光子共振，1 的非线性折射率和三次谐波产生特性在电信范围内与频率密切相关。
• Synthesis and stability studies of conformationally locked 4-(diarylamino)aryl- and 4-(dialkylamino)phenyl-substituted second-order nonlinear optical polyene chromophores
  作者：Katrin Staub、Galina A. Levina、Stephen Barlow、Tony C. Kowalczyk、Hilary S. Lackritz、Marguerite Barzoukas、Alain Fort、Seth R. Marder

  DOI：10.1039/b208024a

  日期：2003.3.19

  A series of chromophores with high second-order nonlinearities has been synthesized; the chromphores consist of triarylamine or dialkylarylamine donors linked by a conformationally locked polyene bridge to a dicyanomethylidene acceptor. The use of bridges of this type, combined with the replacement of dialkylarylamine with triarylamine donors, leads to high thermal stability without adverse affects on the nonlinear optical properties of the chromophores.

  合成了一系列具有高二阶非线性的发色团；发色团由三芳胺或二烷基芳胺供体组成，通过构象锁定多烯桥与二氰基亚甲基受体连接。这种类型的桥的使用，与用三芳胺供体取代二烷基芳胺相结合，导致了高热稳定性，而不会对发色团的非线性光学性质产生不利影响。
• Synthesis of Functionalized Organic Second-Order Nonlinear Optical Chromophores for Electrooptic Applications
  作者：S. Thayumanavan、Jeffrey Mendez、Seth R. Marder

  DOI：10.1021/jo981707v

  日期：1999.6.1

  The design and syntheses of functionalized second-order nonlinear optical chromophores, suitable for covalent incorporation into functionalized high-performance polymers, are described. The chromophores with hydroxy alkyl functionality have diarylamino groups as the donor moiety and a styryl thiophene moiety as the conjugated bridge. The triarylamine parts of the molecules were synthesized using palladium-catalyzed C-N bond forming reactions. The conjugated bridge was assembled using the Wittig reaction. The acceptor groups were installed in the last steps of the syntheses.