蒽-2,3-甲酰亚胺 | 6705-69-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 中文名称: 蒽-2,3-甲酰亚胺
• 英文名称: anthracene-2,3-carboximide
• 英文别名: 1H-naphtho[2,3-f]isoindole-1,3(2H)-dione；naphtho[2,3-f]isoindole-1,3-dione
• CAS: 6705-69-7
• 化学式: C₁₆H₉NO₂
• 分子量: 247.253
• InChiKey: WURUEAGEEANDFN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  蒽-2,3-甲酰亚胺 在 ammonium hydroxide 作用下， 反应 24.0h， 生成 anthracene-2,3-dicarboxamide
  参考文献：
  名称：

  Phthalonaphthalocyanines:  New Far-Red Dyes for Spectral Hole Burning

  摘要：

  Mixed phthalocyanines carrying one anthracene (Pc(3)An) or substituted naphthalene nucleus (Pc(3)NcR(2), R = H, OCH3, or SC12H25) are proposed as low-temperature photochroms for spectral hole burning. Solubility of these compounds in polymers was greatly enhanced by introducing the 2,4-dimethyl-3-pentoxy substituent to the remaining three benzopyrrolic fragments. The wavelengths and intensities of the Q transitions (S-1 and S-2) were measured for two prototropic tautomers having different position of the pair of inner protons. The average energy of the two lowest transitions is very similar in both tautomers, although the S-1-S-2 Splitting is much smaller in the less stable form. The relative equilibrium concentration of the tautomers at room temperature depends on the electron releasing properties of the substituents. This allows one to predict the positions of protons in each form. Absorption dichroism of stretched polyethylene films was used in order to establish the direction of the S-1 and S-2 transition dipole moments in the molecular framework. The tautomers can be completely converted into each other at 10 K by light with quantum yields of (1-2) x 10(-3) and (5-8) x 10(-3), respectively, depending on the direction of the process. Most probably the phototransformation occurs in the vibrationally relaxed triplet state via the tunneling of a single proton which results in an intermediate state with cis-configuration of protons. The photochemically accumulated less stable form decays at higher temperatures (T) as a result of a thermally activated tunneling process at characteristic T of 115 and 153 K for protonated and deuterated Pc(3)Nc, respectively. The strength of linear electron-photon coupling (EPC), which is crucial from the point of view of spectral hole burning, is characterized by Debye-Waller factors (DWFs) about 0.6-0.75, depending on the compound and the polymer matrix. The T dependence of quasihomogeneous hole width (T-qh) obeys a power law with coefficients 2.5 +/- 0.5 (between 6 and 30-45 K). In different polymer hosts, the DWF increases and the hole width decreases in the following order: polystyrene, poly(vinyl butyral) > polyethylene. The strength of EPC for the lowest transitions is similar in both tautomeric forms. A slight enhancement of the EPC strength in the series of dyes Pc(3)Nc(OCH3)(2) similar to Pc(3)Nc < Pc(3)Nc(SC12H25)(2) < Pc(3)An is correlated with the increase of electron-withdrawing power of substituents, plausibly, as a result of the increase of dipole moment change upon electronic excitation. Spectroscopic properties, phototautomerization quantum yields, and the EPC strength of mixed phthalocyanines were compared with those of chlorin and porphyrins.

  DOI：

  10.1021/jp971586n
• 作为产物：
  描述：

  2,3-蒽二甲酸 在 乙酸酐 、 formamide 作用下， 以 xylene 为溶剂， 反应 27.0h， 生成 蒽-2,3-甲酰亚胺
  参考文献：
  名称：

  Phthalonaphthalocyanines:  New Far-Red Dyes for Spectral Hole Burning

  摘要：

  Mixed phthalocyanines carrying one anthracene (Pc(3)An) or substituted naphthalene nucleus (Pc(3)NcR(2), R = H, OCH3, or SC12H25) are proposed as low-temperature photochroms for spectral hole burning. Solubility of these compounds in polymers was greatly enhanced by introducing the 2,4-dimethyl-3-pentoxy substituent to the remaining three benzopyrrolic fragments. The wavelengths and intensities of the Q transitions (S-1 and S-2) were measured for two prototropic tautomers having different position of the pair of inner protons. The average energy of the two lowest transitions is very similar in both tautomers, although the S-1-S-2 Splitting is much smaller in the less stable form. The relative equilibrium concentration of the tautomers at room temperature depends on the electron releasing properties of the substituents. This allows one to predict the positions of protons in each form. Absorption dichroism of stretched polyethylene films was used in order to establish the direction of the S-1 and S-2 transition dipole moments in the molecular framework. The tautomers can be completely converted into each other at 10 K by light with quantum yields of (1-2) x 10(-3) and (5-8) x 10(-3), respectively, depending on the direction of the process. Most probably the phototransformation occurs in the vibrationally relaxed triplet state via the tunneling of a single proton which results in an intermediate state with cis-configuration of protons. The photochemically accumulated less stable form decays at higher temperatures (T) as a result of a thermally activated tunneling process at characteristic T of 115 and 153 K for protonated and deuterated Pc(3)Nc, respectively. The strength of linear electron-photon coupling (EPC), which is crucial from the point of view of spectral hole burning, is characterized by Debye-Waller factors (DWFs) about 0.6-0.75, depending on the compound and the polymer matrix. The T dependence of quasihomogeneous hole width (T-qh) obeys a power law with coefficients 2.5 +/- 0.5 (between 6 and 30-45 K). In different polymer hosts, the DWF increases and the hole width decreases in the following order: polystyrene, poly(vinyl butyral) > polyethylene. The strength of EPC for the lowest transitions is similar in both tautomeric forms. A slight enhancement of the EPC strength in the series of dyes Pc(3)Nc(OCH3)(2) similar to Pc(3)Nc < Pc(3)Nc(SC12H25)(2) < Pc(3)An is correlated with the increase of electron-withdrawing power of substituents, plausibly, as a result of the increase of dipole moment change upon electronic excitation. Spectroscopic properties, phototautomerization quantum yields, and the EPC strength of mixed phthalocyanines were compared with those of chlorin and porphyrins.

  DOI：

  10.1021/jp971586n

文献信息

• Electroactive polymers, manufacturing process thereof, electrode and use thereof
  申请人：EVONIK DEGUSSA GmbH

  公开号：US10103384B2

  公开（公告）日：2018-10-16

  Disclosed is an oligomeric or polymeric compound comprising at least two structural units of formula (I) wherein Ar is a carbocyclic aromatic radical or a heterocyclic aromatic radical with the two carbonyl carbon atoms being attached to two ring carbon atoms of the Ar group forming together with the imide-nitrogen atom a five-membered or a six-membered ring X is a divalent group selected from —CR1R2—, —CO—, —SiR3R4—, —P(O)R5—, —P(O)(OR6)—, —PR7—, —P(OR8)—, —S(O)— or —S(O)2—. R1 to R8 independently of one another are hydrogen, alkyl, cycloalkyl, aryl or heteroaryl groups, R9 is a divalent hydrocarbon group or a covalent bond, and R10, R11 and R12 independently of one another are hydrogen or C1-C6 alkyl or R10 and R11 or R10 and R12 together with the carbon atoms to which they are attached form a cycloaliphatic ring or a bicyclic aliphatic system The oligomeric or polymeric compound comprising units of formula (I) of the invention can be used as redox-active material in storage means for electric energy, for example in batteries, redox-flow cells, fuel cells or capacitors.

  本发明公开了一种低聚物或聚合物化合物，该化合物包含至少两个式（I）的结构单元 其中 Ar 是碳环芳香基或杂环芳香基，两个羰基碳原子连接到 Ar 基团的两个环碳原子上，与亚胺氮原子一起形成五元环或六元环 X 是二价基团，选自-CR1R2-、-CO-、-SiR3R4-、-P(O)R5-、-P(O)(OR6)-、-PR7-、-P(OR8)-、-S(O)-、-CO-、-SiR3R4-、-P(O)R5-、-P(O)(OR6)-、-PR7-、-P(OR8)-、-S(O)-或-S(O)2-。R1 至 R8 相互独立地为氢、烷基、环烷基、芳基或杂芳基，R9 为二价烃基或共价键，R10、R10、R11 和 R12 相互独立地为氢或 C1-C6 烷基，或 R10 和 R11 或 R10 和 R12 与它们所连接的碳原子一起形成环脂族环或双环脂族体系。 本发明由式（I）单元组成的低聚物或聚合物化合物可用作电能储存装置中的氧化还原活性材料，例如电池、氧化还原流电池、燃料电池或电容器。
• CYCLIC IMIDE-SUBSTITUTED PYRIDYLALKANE, ALKENE, AND ALKINE CARBOXAMIDES USEFUL AS CYTOSTATIC AND IMMUNOSUPPRESSIVE AGENTS
  申请人：Klinge Pharma GmbH

  公开号：EP1042315B1

  公开（公告）日：2004-04-14
• Vorotnikov, A. M.; Kopranenkov, V. N.; Luk'yanets, E. A., Journal of general chemistry of the USSR, 1991, vol. 61, # 5.2, p. 1128 - 1130
  作者：Vorotnikov, A. M.、Kopranenkov, V. N.、Luk'yanets, E. A.

  DOI：——

  日期：——
• Ring-expanded porphyrins as an approach towards highly conductive molecular semiconductors
  作者：Nagao Kobayashi、W. Andrew Nevin、Satoshi Mizunuma、Hiroshi Awaji、Minori Yamaguchi

  DOI：10.1016/0009-2614(93)85165-k

  日期：1993.4

  As an approach to obtaining molecular semiconductors with high conductivity, it was attempted to lower the activation energy of conduction by enlarging the pi-conjugated system in porphyrin materials. An anthraporphyrin (ZnTAnP) has been synthesized for the first time, and the spectroscopic, electrochemical and semiconductive properties have been characterized as a function of increasing molecular size, in the order: tetraphenylporphyrin (ZnTPP), tetrabenzoporphyrin (ZnTBP), tetranaphthaloporphyrin (ZnTNP), and ZnTAnP. With enlargement of the macrocycle, the Q band shifts to the red, and the absolute values of oxidation and reduction potentials become smaller. Room temperature conductivities of air-doped ZnTPP, ZnTBP, ZnTNP, and ZnTAnP thin films are < 10(-11), 4 X 10(-10), 3 X 10(-4) and 1 X 10(-7) OMEGA-1 cm-1, respectively. The smaller conductivity of ZnTAnP appears due to the formation of a stable charge transfer complex with oxygen.
• Vorotnikov, A. M.; Kopranenkov, V. N.; Luk'yanets, E. A., Journal of general chemistry of the USSR, 1991, vol. 61, p. 1128 - 1130
  作者：Vorotnikov, A. M.、Kopranenkov, V. N.、Luk'yanets, E. A.

  DOI：——

  日期：——