N,N'-bis(2,6-diisopropylphenyl)-1-bromoperylene-3,4,9,10-tetracarboxydiimide | 869276-74-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: N,N'-bis(2,6-diisopropylphenyl)-1-bromoperylene-3,4,9,10-tetracarboxydiimide
• 英文别名: 11-Bromo-7,18-bis[2,6-di(propan-2-yl)phenyl]-7,18-diazaheptacyclo[14.6.2.22,5.03,12.04,9.013,23.020,24]hexacosa-1(23),2,4,9,11,13,15,20(24),21,25-decaene-6,8,17,19-tetrone
• CAS: 869276-74-4
• 化学式: C₄₈H₄₁BrN₂O₄
• 分子量: 789.769
• InChiKey: UKFHYEDSGPCBBY-UHFFFAOYSA-N

物化性质

• 熔点：
  >280 °C
• 密度：
  1.392±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  12
• 重原子数：
  55
• 可旋转键数：
  6
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  74.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N,N'-bis(2,6-diisopropylphenyl)-1-bromoperylene-3,4,9,10-tetracarboxydiimide 在 potassium carbonate 、 potassium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 以76%的产率得到7,18-Bis[2,6-di(propan-2-yl)phenyl]-11-hydroxy-7,18-diazaheptacyclo[14.6.2.22,5.03,12.04,9.013,23.020,24]hexacosa-1(23),2,4,9,11,13,15,20(24),21,25-decaene-6,8,17,19-tetrone
  参考文献：
  名称：

  Photonic Logic Gates Based on Control of FRET by a Solvatochromic Perylene Bisimide

  摘要：

  New perylenebisimide derivatives hydroxyperylenebisimide and naphthoperylenebisimide were obtained and applied to construct a new solvatochromic dyad 9. The solvatochromic behavior of hydroxyperylenebisimide was studied, and the structure of naphthoperylenebisimide was determined by X-ray crystallography. The spectral studies indicated that the hydroxyperylenebisimide and naphthoperylenebisimide units of dyad 9 were strongly coupled in the ground state, and as a result the fluorescence of the naphthoperylenebisimide unit was almost quenched and that of the hydroxyperylenebisimide unit was greatly enhanced due to the fluorescence resonance energy transfer (FRET). As we expected, this FRET process could be tuned with the addition of protons, base, and ferric ions. This behavior of dyad 9 could be interpreted by a two-input INH logic gate, while in the presence of Fe(III), the ion complex of 9 could execute a two-input XOR logic gate. By changing the output signal, a combinational logic circuit with three inputs could also be interpreted.

  DOI：

  10.1021/jo0624748
• 作为产物：
  描述：

  3,4,9,10-苝四羧酸二酐 在 硫酸 、 溴 、 碘 、 溶剂黄146 作用下， 以 N-甲基吡咯烷酮 为溶剂， 生成 N,N'-bis(2,6-diisopropylphenyl)-1-bromoperylene-3,4,9,10-tetracarboxydiimide
  参考文献：
  名称：

  新型co烯发色团的简便合成与表征及其在LCD彩色滤光片中的应用

  摘要：

  通过一步反应，由N，N'-双（2,6-二异丙基苯基）-1,7-二溴，-3,4,9,10-四羧二酰亚胺合成了新的二苯并呋喃衍生物四苯基二酰亚胺和单苯基苯并per四丁基二酰亚胺。在沿per的短分子轴扩展芳族体系的方法中，建议的合成路线是最简单，最经济的方法。合成的分子显示出优异的稳定性和色强度，为黄色生色团。它们的特征是与per四甲二酰亚胺相比，吸收的显着变色变化和高荧光量子产率。

  DOI：

  10.1016/j.dyepig.2011.11.009

文献信息

• A study on the fluorescence property of the perylene derivatives with methoxy groups
  作者：Jeong Yun Kim、Sung Wun Woo、Jin Woong Namgoong、Jae Pil Kim

  DOI：10.1016/j.dyepig.2017.08.060

  日期：2018.1

  conducted. The methoxy groups of terminal-substituents had a lesser effect on fluorescence quenching than the methoxy groups of bay-substituents. Moreover, only the methoxy groups at the para-position of the bay-substituents strongly affected on fluorescence quenching. These results showed that the fluorescence of the dyes are influenced by the electron donating effect of the methoxy groups when the

  合成了在各个位置带有甲氧基的基染料，以了解甲氧基对荧光猝灭的影响。另外，还合成了用乙基代替甲氧基的per基染料作为对照。测量了染料的吸收和荧光性质，然后进行了密度泛函理论（DFT）和时间相关的密度泛函理论（TD-DFT）模拟。末端取代基的甲氧基对荧光猝灭的影响小于海湾取代基的甲氧基。此外，仅海湾取代基对位的甲氧基强烈影响荧光猝灭。
• 퍼릴렌 비스이미드계 화합물 및 이를 포함하는 염료
  申请人：LG CHEM, LTD. 주식회사 엘지화학(120010134563) Corp. No ▼ 110111-2207995BRN ▼107-81-98139

  公开号：KR101644228B1

  公开（公告）日：2016-07-29

  본 명세서는 신규한 퍼릴렌 비스이미드계 화합물 및 이를 포함하는 염료를 제공한다.

  本规范提供了新型的聚乙烯亚胺基化合物以及包含该化合物的染料。
• ＬＣＤ용 고투과 황색 염료 및 그 제조 방법
  申请人：LG Display Co.,Ltd. 엘지디스플레이 주식회사(119981018655) Corp. No ▼ 110111-0393134

  公开号：KR102051911B1

  公开（公告）日：2019-12-04

  본 발명은 LCD용 고투과 황색 염료, 상기 염료를 포함하는 염료 분산체, 상기 염료 분산체를 포함하는 착색 조성물, 상기 착색 조성물을 포함하는 컬러 필터 및 상기 염료의 제조 방법에 관한 것이다.

  本发明涉及LCD用高透过黄色染料，包括所述染料的染料分散体，包括所述染料分散体的着色组合物，包括所述着色组合物的彩色滤光片以及有关所述染料的制备方法。
• Synthesis and characterization of novel perylene dyes with new substituents at terminal-position as colorants for LCD color filter
  作者：Jeong Yun Kim、Jun Choi、Jin Woong Namgoong、Se Hun Kim、Chun Sakong、Sim Bum Yuk、Sang-a Choi、Woosung Lee、Jae Pil Kim

  DOI：10.1007/s10847-015-0532-9

  日期：2015.6

  Six novel red perylene dyes were synthesized by modifying the bay- and terminal-positions of perylene main body to improve the optical performances of liquid crystal display (LCD) color filters. The absorption properties, solubility in industrial solvents and thermal stabilities of the dyes were examined to evaluate the dyes for dye-based LCD color filter. Mill bases and spin-coated color filters were formulated and fabricated using the synthesized dyes. Transmittance, dye aggregation and thermal stabilities of the prepared color filters were investigated using a color spectrophotometer. Geometric structures of the synthesized dyes were optimized by using Gaussian program. Five of the synthesized dyes showed acceptable optical properties as colorants for LCD color filters. Also, the synthesized dyes and prepared color filters exhibited suitable thermal stability for the application. Furthermore, the prepared color filters exhibited superior transmittances than pigment-based color filters at 650 nm. Their physical properties were closely related with chemical structures investigated by geometry optimization.

  合成了六种新型红色萤光素，通过修改萤光素主体的贝位和端位，以改善液晶显示(LCD)彩色滤光片的光学性能。对这些染料的吸收特性、在工业溶剂中的溶解性和热稳定性进行了研究，以评估其作为染料基LCD彩色滤光片的表现。使用合成的染料制备了磨料基础和旋涂彩色滤光片。通过色彩光谱仪对制备的彩色滤光片的透过率、染料聚集情况和热稳定性进行了研究。使用Gaussian程序优化了合成染料的几何结构。五种合成染料显示出作为LCD彩色滤光片颜料的可接受光学特性。此外，合成染料和制备的彩色滤光片表现出适合应用的热稳定性。此外，制备的彩色滤光片在650 nm处的透过率优于基于颜料的彩色滤光片。它们的物理性质与几何优化研究的化学结构密切相关。
• The effect of fluorescence of perylene red dyes on the contrast ratio of LCD color filters
  作者：Jeong Yun Kim、Chun Sakong、Sang-a Choi、Hyeyoun Jang、Se Hun Kim、Kil Seong Chang、Myoung Sic Han、Jeong Su Lee、Jae Pil Kim

  DOI：10.1016/j.dyepig.2016.03.041

  日期：2016.8

  between dye fluorescence and the optical properties of color filters was investigated. Six perylene-based dyes were synthesized, and dye-based and pigment-dye hybrid color filters were prepared with each dye. The fluorescence properties of the synthesized dyes in solution and the prepared color filters were evaluated. The maximum brightness and the contrast ratio of the color filters were measured, from

  建议使用染料基和颜料染料混合滤色镜，以克服诸如传统颜料基滤色镜的光散射之类的缺点。但是，用作LCD彩色滤光片着色剂的染料可能会显示强荧光。荧光通过增加全黑状态下的亮度来降低滤色器的对比度，并影响显示器的光学性能。在这项研究中，研究了染料荧光与滤色镜的光学特性之间的相关性。合成了六种基于ylene的染料，并分别为每种染料制备了基于染料和染料的混合彩色滤光片。评价溶液中合成的染料和制备的滤色片的荧光性质。测量滤色片的最大亮度和对比度，从中可以计算出滤色片的最小亮度。由于在可见光区域的发射，所有基于染料的和颜料-染料混合的彩色滤光片均比基于颜料的彩色滤光片显示出更高的最小亮度。