4-[2-(4,6-diamino-[1,3,5]triazin-2-yl)vinyl]-benzaldehyde

• 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: 4-[2-(4,6-diamino-[1,3,5]triazin-2-yl)vinyl]-benzaldehyde
• 英文别名: 4-[(E)-2-(4,6-diamino-1,3,5-triazin-2-yl)ethenyl]benzaldehyde
• 化学式: C₁₂H₁₁N₅O
• 分子量: 241.252
• InChiKey: BKGTYZWHIAHUNR-AATRIKPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  108
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  巴比妥酸 、 4-[2-(4,6-diamino-[1,3,5]triazin-2-yl)vinyl]-benzaldehyde 在 硫酸 作用下， 以 戊醇 、 水 为溶剂， 反应 0.17h， 以88%的产率得到5-{4-[2-(4,6-diamino-[1,3,5]triazin-2-yl)vinyl]-benzylidene}-pyrimidine-2,4,6-trione
  参考文献：
  名称：

  Vapor Phase Self-Assembly of Electrooptic Thin Films via Triple Hydrogen Bonds

  摘要：

  The donor-acceptor pi-electron chromophore 5-{4-[2-(4,6-diamino-[1,3,5]triazin-2-yl)-vinyl]-benzylidene}-pyrimidine-2,4,6-trione (DTPT) was designed and synthesized. Triple H-bonding interactions between neighboring molecules direct self-assembled chromophore alignment in a head-to-tail orientation using a straightforward vapor phase deposition process. Angle-dependent SHG interference patterns and the quadratic dependence of the 532 nm light output intensity on the thickness of the DTPT films for glass substrates coated on both sides demonstrate high, reproducible film quality and uniformity. XRD also demonstrates long-range order in the film and yields a molecular tilt angle in good agreement with polarized SHG data, clearly showing that out-of-plane ordering of chromophore molecules has been achieved.

  DOI：

  10.1021/ja037164a
• 作为产物：
  描述：

  2,4-二氨基-6-甲基-1,3,5-三嗪 、 对苯二甲醛 在 硫酸 作用下， 以 甲醇 为溶剂， 反应 8.0h， 以41%的产率得到4-[2-(4,6-diamino-[1,3,5]triazin-2-yl)vinyl]-benzaldehyde
  参考文献：
  名称：

  Vapor Phase Self-Assembly of Electrooptic Thin Films via Triple Hydrogen Bonds

  摘要：

  The donor-acceptor pi-electron chromophore 5-{4-[2-(4,6-diamino-[1,3,5]triazin-2-yl)-vinyl]-benzylidene}-pyrimidine-2,4,6-trione (DTPT) was designed and synthesized. Triple H-bonding interactions between neighboring molecules direct self-assembled chromophore alignment in a head-to-tail orientation using a straightforward vapor phase deposition process. Angle-dependent SHG interference patterns and the quadratic dependence of the 532 nm light output intensity on the thickness of the DTPT films for glass substrates coated on both sides demonstrate high, reproducible film quality and uniformity. XRD also demonstrates long-range order in the film and yields a molecular tilt angle in good agreement with polarized SHG data, clearly showing that out-of-plane ordering of chromophore molecules has been achieved.

  DOI：

  10.1021/ja037164a

文献信息

• Vapor deposited electro-optic films self-assembled through hydrogen bonding
  申请人：Marks J. Tobin

  公开号：US20050127337A1

  公开（公告）日：2005-06-16

  The present invention introduces a novel route toward microstructural orientation into organic films, using multiple hydrogen-bonding to self-assemble chromophore molecules into electro-optic films in a net polar orientation. High-quality, thick films (up to micrometers) with molecular net dipole orientations can be fabricated under vacuum in hours. The film microstructure is intrinsically acentric; and the orientation is robust.

  本发明引入了一种新的方法，通过使用多重氢键自组装色团分子成为电光薄膜，使有机薄膜中的微观结构定向。高质量、厚度达到微米级别的薄膜可以在几小时内在真空中制备，并具有分子净偶极取向。薄膜的微观结构本质上是非心对称的，取向是稳健的。
• US7291293B2
  申请人：——

  公开号：US7291293B2

  公开（公告）日：2007-11-06
• [EN] VAPOR DEPOSITED ELECTRO-OPTIC FILMS SELF-ASSEMBLED THROUGH HYDROGEN BONDING<br/>[FR] FILMS ELECTRO-OPTIQUES DEPOSES PAR EVAPORATION SOUS VIDE AUTOASSEMBLES PAR UNE LIAISON HYDROGENE
  申请人：UNIV NORTHWESTERN

  公开号：WO2004079434A2

  公开（公告）日：2004-09-16

  The present invention introduces a novel route toward microstructural orientation into organic films, using multiple hydrogen-bonding to self-assemble chromophore molecules into electro-optic films in a net polar orientation. High­quality, thick films (up to micrometers) with molecular net dipole orientations can be fabricated under vacuum in hours. The film microstructure is intrinsically acentric; and the orientation is robust.
• Vapor Phase Self-Assembly of Electrooptic Thin Films via Triple Hydrogen Bonds
  作者：Peiwang Zhu、Hu Kang、Antonio Facchetti、Guennadi Evmenenko、Pulak Dutta、Tobin J. Marks

  DOI：10.1021/ja037164a

  日期：2003.9.1

  The donor-acceptor pi-electron chromophore 5-4-[2-(4,6-diamino-[1,3,5]triazin-2-yl)-vinyl]-benzylidene}-pyrimidine-2,4,6-trione (DTPT) was designed and synthesized. Triple H-bonding interactions between neighboring molecules direct self-assembled chromophore alignment in a head-to-tail orientation using a straightforward vapor phase deposition process. Angle-dependent SHG interference patterns and the quadratic dependence of the 532 nm light output intensity on the thickness of the DTPT films for glass substrates coated on both sides demonstrate high, reproducible film quality and uniformity. XRD also demonstrates long-range order in the film and yields a molecular tilt angle in good agreement with polarized SHG data, clearly showing that out-of-plane ordering of chromophore molecules has been achieved.