9,10-[1,2]Benzeno-9,10-二氢蒽-2,3,6,7-四羧酸 | 945681-55-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 中文名称: 9,10-[1,2]Benzeno-9,10-二氢蒽-2,3,6,7-四羧酸
• 英文名称: triptycene-2,3,6,7-tetracarboxylic acid
• 英文别名: 9,10-Dihydro-9,10-[1,2]benzenoanthracene-2,3,6,7-tetracarboxylic acid；pentacyclo[6.6.6.02,7.09,14.015,20]icosa-2,4,6,9,11,13,15,17,19-nonaene-4,5,11,12-tetracarboxylic acid
• CAS: 945681-55-0
• 化学式: C₂₄H₁₄O₈
• 分子量: 430.37
• InChiKey: BAISXRRJJTZVGI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  32
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  149
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  9,10-[1,2]Benzeno-9,10-二氢蒽-2,3,6,7-四羧酸 在 cesium hydroxide 、 lithium aluminium tetrahydride 、 硫酸 、 氢溴酸 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 212.5h， 生成 9,25-Bis[4,5-bis(butylsulfanyl)-1,3-dithiol-2-ylidene]-6,8,10,12,22,24,26,28-octathianonacyclo[15.15.6.02,16.04,14.07,11.018,32.020,30.023,27.033,38]octatriaconta-2(16),3,7(11),14,18(32),19,23(27),30,33,35,37-undecaene
  参考文献：
  名称：

  Tetrathiafulvalene-functionalized triptycenes: synthetic protocols and elucidation of intramolecular Coulomb repulsions in the oxidized species

  摘要：

  A large selection of triptycenes functionalized with tetrathiafulvalene (TTF) units as well as triptycenes containing extended TTFs as a part of the triptycene core have been synthesized utilizing new triptycene di- and tetraaldehydes as well as bis-, tetrakis- and hexakis(bromomethyl) derivatives. The largest scaffold contains a total of 12 TTFs around the central triptycene core. From spectroelectro-chemical and chemical oxidation studies, we have elucidated the extent to which an increasing number of electrostatic interactions among oxidized TTF units exert an influence on the absorption characteristics. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.06.020
• 作为产物：
  描述：

  2,3,6,7-tetramethyltriptycene 在 potassium permanganate 作用下， 以 吡啶 、 水 为溶剂， 反应 24.0h， 以94%的产率得到9,10-[1,2]Benzeno-9,10-二氢蒽-2,3,6,7-四羧酸
  参考文献：
  名称：

  高度对称的三蝶烯四和六羧酸盐的合成

  摘要：

  已在标题化合物的合成中检验了两种替代方法，均从容易获得的四甲基蒽开始，并采用 Diels-Alder 加成作为关键反应步骤。

  DOI：

  10.1055/s-2007-966042

文献信息

• [EN] POLYMERS FOR USE IN ELECTRONIC DEVICES<br/>[FR] POLYMÈRES DESTINÉS À ÊTRE UTILISÉS DANS DES DISPOSITIFS ÉLECTRONIQUES
  申请人：DUPONT ELECTRONICS INC

  公开号：WO2020018621A1

  公开（公告）日：2020-01-23

  Disclosed is a dianhydride having Formula (I). In Formula (I): Q1 is CR4, SiR4, GeR4, PR4, or N; Q2 is CR5, SiR5, GeR5, PR5, or N; R1, R2, and R3 are the same or different at each occurrence and are F, CN, alkyl, fluoroalkyl, unsubstituted or substituted hydrocarbon aryl, unsubstituted or substituted heteroaryl, alkoxy, fluoroalkoxy, unsubstituted or substituted aryloxy, silyl, or siloxy, where adjacent R1 groups can be joined together to form a fused aromatic ring; R4 and R5 are the same or different and are H, F, CN, alkyl, fluoroalkyl, unsubstituted or substituted hydrocarbon aryl, unsubstituted or substituted heteroaryl, alkoxy, fluoroalkoxy, unsubstituted or substituted aryloxy, silyl, or siloxy; a is an integer from 0-4; b and c are the same or different and are an integer from 0-2; and the double dashed lines between two rings indicate that the two rings can be fused at any available position.

  揭示的是具有化学式（I）的二酐。在化学式（I）中：Q1是CR4、SiR4、GeR4、PR4或N；Q2是CR5、SiR5、GeR5、PR5或N；R1、R2和R3在每个出现位置上均相同或不同，可以是F、CN、烷基、氟烷基、未取代或取代的碳氢基芳基、未取代或取代的杂芳基、烷氧基、氟烷氧基、未取代或取代的芳氧基、硅基或硅氧基，其中相邻的R1基团可以连接在一起形成融合的芳香环；R4和R5相同或不同，可以是H、F、CN、烷基、氟烷基、未取代或取代的碳氢基芳基、未取代或取代的杂芳基、烷氧基、氟烷氧基、未取代或取代的芳氧基、硅基或硅氧基；a是0-4之间的整数；b和c相同或不同，是0-2之间的整数；两个环之间的双虚线表示这两个环可以在任何可用位置融合。
• Synthesis of Highly Symmetrical Triptycene Tetra- and Hexacarboxylates
  作者：Jiří Závada、Markéta Rybáčková、Martin Bělohradský、Petr Holý、Radek Pohl、Václav Dekoj

  DOI：10.1055/s-2007-966042

  日期：——

  Two alternative procedures, both starting from easily accessible- tetramethylanthracenes and employing the Diels-Alder addition as the key reaction step(s), have been examined in the synthesis of the title compounds.

  已在标题化合物的合成中检验了两种替代方法，均从容易获得的四甲基蒽开始，并采用 Diels-Alder 加成作为关键反应步骤。
• Microporous aromatic polyimides derived from triptycene-based dianhydride
  作者：You-Hua Xiao、Yu Shao、Xu-Xu Ye、Hao Cui、De-Lian Wang、Xia-Heng Zhou、Sheng-Ling Sun、Lin Cheng

  DOI：10.1016/j.cclet.2015.12.018

  日期：2016.3

  A novel triptycene-based dianhyride as a shape-persistent building block with high internal free volume was conveniently synthesized via solvothermal method. Subsequently, three all-aromatic polyimides, PIa, PIb and PIc, were prepared by a one-step polycondensation of triptycene-2,3,6,7-tetracarboxylic dianhydride with 2,2'-bis(trifluoromethyl)benzidine, m-tolidine and 3,3',5,5'-tetramethylbenzidine, respectively. The corresponding polymers exhibit good solubility, excellent thermal stability, significant microporosity with large BET surface areas of up to 623 m(2) g(-1), as well as an unexpected optical property with a transmittance of similar to 85% at 450 nm as similar to 20 mu m membranes. (C) 2016 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.
• Tetrathiafulvalene-functionalized triptycenes: synthetic protocols and elucidation of intramolecular Coulomb repulsions in the oxidized species
  作者：Jiří Rybáček、Markéta Rybáčková、Martin Høj、Martin Bělohradský、Petr Holý、Kristine Kilså、Mogens Brøndsted Nielsen

  DOI：10.1016/j.tet.2007.06.020

  日期：2007.9

  A large selection of triptycenes functionalized with tetrathiafulvalene (TTF) units as well as triptycenes containing extended TTFs as a part of the triptycene core have been synthesized utilizing new triptycene di- and tetraaldehydes as well as bis-, tetrakis- and hexakis(bromomethyl) derivatives. The largest scaffold contains a total of 12 TTFs around the central triptycene core. From spectroelectro-chemical and chemical oxidation studies, we have elucidated the extent to which an increasing number of electrostatic interactions among oxidized TTF units exert an influence on the absorption characteristics. (c) 2007 Elsevier Ltd. All rights reserved.