1,6,7,12-tetrachloro-3,4,9,10-perylenetetracarboxylic acid bis(methylimide) | 106342-00-1

• 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: 1,6,7,12-tetrachloro-3,4,9,10-perylenetetracarboxylic acid bis(methylimide)
• 英文别名: Anthra[2,1,9-def:6,5,10-d'e'f']diisoquinoline-1,3,8,10(2H,9H)-tetrone, 5,6,12,13-tetrachloro-2,9-dimethyl-；11,14,22,26-tetrachloro-7,18-dimethyl-7,18-diazaheptacyclo[14.6.2.22,5.03,12.04,9.013,23.020,24]hexacosa-1(22),2(26),3,5(25),9,11,13,15,20,23-decaene-6,8,17,19-tetrone
• CAS: 106342-00-1
• 化学式: C₂₆H₁₀Cl₄N₂O₄
• 分子量: 556.188
• InChiKey: PQGOXPDIJYEGLE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  36
• 可旋转键数：
  0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.08
• 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：

  1,6,7,12-tetrachloro-3,4,9,10-perylenetetracarboxylic acid bis(methylimide) 、 苯硼酸 在 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 乙醇 、 水 、 甲苯 为溶剂， 以51%的产率得到
  参考文献：
  名称：

  湾区交错芳烃取代基的手性苝双酰亚胺染料

  摘要：

  通过Suzuki交叉偶联反应合成了一系列1、6、7、12位具有不同芳基取代基的苝双酰亚胺（PBI）染料。由于海湾位置芳基取代基造成的高空间拥挤，这些分子表现出异常大且构象固定的 PBI π核心扭转角。对苯基、萘基和芘基官能化 PBI 的单晶 X 射线分析揭示了互锁的π-π堆积基序，从而导致构象手性以及通过半制备 HPLC 分离对映体纯阻转异构体的可能性。对于四苯基和四-2-萘基取代的衍生物，互锁排列赋予这些分子约120 kJ mol -1的显着外消旋势垒，这是轴向手性PBI的最高外消旋势垒之一。变温NMR研究揭示了溶液中存在多达14种构象异构体，它们通过约65 kJ mol -1的较小活化势垒相互转化。这些核扭曲PBI的氧化还原和光学性质已通过循环伏安法、紫外/可见/近红外和荧光光谱进行了表征，并且它们各自的阻转对映体通过圆二色性（CD）和圆偏振发光（CPL）光谱进行了进一步表征。

  DOI：

  10.1002/chem.202101877
• 作为产物：
  描述：

  颜料红179 在 碘 氯磺酸 作用下， 反应 20.0h， 以3.0 g的产率得到1,6,7,12-tetrachloro-3,4,9,10-perylenetetracarboxylic acid bis(methylimide)
  参考文献：
  名称：

  Lasing action in a family of perylene derivatives: singlet absorption and emission spectra, triplet absorption and oxygen quenching constants, and molecular mechanics and semiempirical molecular orbital calculations

  摘要：

  We present experimental and computational determinations of the excited-state properties in several perylene dyestuffs that are potential candidates for use as laser dyes. Attention is focused on the following species derived from 3,4,9,10-perylenetetracarboxylic acid dianhydride: the bis((2,6-dimethylphenyl)imide) (1b, DXP); the bis(methylimide) (1c, DMP); both 1,6,7,12-tetrachloro- (1d, Cl4DMP) and 1,2,5,6,7,8,11,12-octachloro- (1e, Cl8DMP) derivatives. Soluble derivatives of seven-ringed or larger aromatic systems are produced by the introduction of relatively rigid out-of-plane substituents that prevent intermolecular close packing. Chiral distortions in ring-chlorinated perylene derivatives significantly alter the shape of the absorption bands, a consequence of symmetry breaking. Triplet-triplet absorptions and oxygen-quenching rates are observed under the conditions found in a dye laser cavity. Semiempirical molecular orbital calculations (INDO/S) provide detailed mapping of the singlet and triplet excited state manifolds of DMP, Cl4DMP, and Cl8DMP. Computed transition energies and intensities are used in the interpretation of the spectral features, in particular the observed T1 --> T(n) and potential S1 --> S(n) absorptions. We conclude that perylene-3,4,9,10-tetracarboxylic acid diimide chromophores may be solubilized and utilized in laser materials exhibiting superior performance in terms of power output, tuning range, and light stability.

  DOI：

  10.1021/j100199a032

文献信息

• LIQUID CRYSTALLINE RYLENE TETRACARBOXYLIC ACID DERIVATIVES AND USE THEREOF
  申请人：Koenemann Martin

  公开号：US20110042651A1

  公开（公告）日：2011-02-24

  The present invention relates to liquid-crystalline rylenetetracarboxylic acid derivatives, to processes for their preparation and to their use as n-type organic semiconductors for producing organic field-effect transistors and solar cells.

  本发明涉及液晶芳纶四羧酸衍生物，其制备方法以及作为n型有机半导体用于制造有机场效应晶体管和太阳能电池的用途。
• METHOD FOR PRODUCING ORGANIC FIELD-EFFECT TRANSISTORS
  申请人：Koenemann Martin

  公开号：US20080017850A1

  公开（公告）日：2008-01-24

  A method for producing an organic field-effect transistor, comprising the steps of: a) providing a substrate comprising a gate structure, a source electrode and a drain electrode located on the substrate, and b) applying an n-type organic semiconducting compound to the area of the substrate where the gate structure, the source electrode and the drain electrode are located, wherein the n-type organic semiconducting compound is selected from the group consisting of compounds of the formula I wherein R 1 , R 2 , R 3 and R 4 are independently hydrogen, chlorine or bromine, with the proviso that at least one of these radicals is not hydrogen, Y 1 is O or NR a , wherein R a is hydrogen or an organyl residue, Y 2 is O or NR b , wherein R b is hydrogen or an organyl residue, Z 1 , Z 2 , Z 3 and Z 4 are O, where, in the case that Y 1 is NR a , one of the residues Z 1 and Z 2 may be a NR c group, where R a and R c together are a bridging group having 2 to 5 atoms between the terminal bonds, where, in the case that Y 2 is NR b , one of the residues Z 3 and Z 4 may be a NR d group, where R b and R d together are a bridging group having 2 to 5 atoms between the terminal bonds.
• VERFAHREN ZUR HERSTELLUNG VON MIT RYLENTETRACARBONSAEUREDIIMIDEN BESCHICHTETEN SUBSTRATEN
  申请人：Konemann Martin

  公开号：US20090078312A1

  公开（公告）日：2009-03-26

  The present invention relates to a process for producing a substrate coated with rylenetetracarboximides, in which a substrate is treated with an N,N′-bisubstituted rylenetetracarboximide and the treated substrate is heated to a temperature at which the N,N′-bisubstituted rylenetetracarboximide is converted to the corresponding N,N′-unsubstituted compound. The present invention further relates to semiconductor units, organic solar cells, excitonic solar cells and organic light-emitting diodes which comprise a substrate produced by this process. The present invention further relates to a process for preparing N,N′-unsubstituted rylenetetracarboximides, in which the corresponding N,N′-bisubstituted rylenetetracarboximides are provided and heated to a temperature at which these compounds are converted to the corresponding N,N′-unsubstituted compounds.
• Coatable Polymer Polarizer
  申请人：Light Polymers Holding

  公开号：US20160266292A1

  公开（公告）日：2016-09-15

  A coatable polymer polarizer may be formed with a composition that includes a rigid rod-like polymer capable of forming a liquid crystal phase in a solvent. The rigid rod-like polymer may form an achromatic polarizer.
• ORGANIC SEMICONDUCTOR COMPOSITION COMPRISING A LIQUID MEDIUM
  申请人：BASF SE

  公开号：US20170250347A1

  公开（公告）日：2017-08-31

  Disclosed are a novel semiconductor composition comprising at least one organic semiconductor in a liquid medium and the use thereof the production of organic semiconductor devices, in particular organic field effect transistors, organic solar cells, light-emitting diodes and sensors.