anthraquinone-2-propaneacetal | 194299-34-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: anthraquinone-2-propaneacetal
• 英文别名: 2-(1,3-Dioxan-2-yl)anthra-9,10-quinone；2-(1,3-dioxan-2-yl)anthracene-9,10-dione
• CAS: 194299-34-8
• 化学式: C₁₈H₁₄O₄
• 分子量: 294.307
• InChiKey: DXYSEXLLLDMTFJ-UHFFFAOYSA-N

物化性质

• 沸点：
  501.8±50.0 °C(Predicted)
• 密度：
  1.323±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  anthraquinone-2-propaneacetal 在 盐酸 、 正丁基锂 作用下， 以 丙酮 为溶剂， 反应 1.0h， 生成 2-formyl-9,10-bis(4,5-dimethylthio-1,3-dithiol-2-ylidene)dihydroanthracene
  参考文献：
  名称：

  Synthesis and Properties of the First Highly Conjugated Tetrathiafulvalene Analogues Covalently Attached to [60]Fullerene

  摘要：

  The synthesis of the first C-60-based donor-acceptor (D-A) systems (12a-c) in which the C-60 core is covalently linked to strong, highly conjugated pi-electron donors derived of tetrathiafulvalene (TTF) with p-quinodimethane structure has been carried out by cyclization with azomethine ylides following Prate's procedure. The synthetic strategy requires the preparation of the novel formyl-substituted pi-extended donors which, in turn, are prepared in a multistep synthetic procedure by reaction of 2-formyl-9,10-anthraquinone (6) with the appropriately substituted phosphonate esters (8). Semiempirical PM3 calculations predict a geometry highly distorted from planarity for the donor fragment and a most stable conformation in which both 1,3-dithiole rings are far away from the [60]fullerene surface. The redox properties were determined by cyclic voltammetry in solution and reveal the presence of four cathodically shifted reduction waves, relative to C-60 and corresponding to the C-60 core, and a two-electron single oxidation wave to form stable dication species of the pi-extended donor units. Magnetic susceptibility measurements clearly indicate a paramagnetic behavior in the solid state, and a remarkable conductivity is observed for these single component organic compounds.

  DOI：

  10.1021/jo970320+
• 作为产物：
  描述：

  2-羟甲基蒽醌 在 对甲苯磺酸 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 60.0h， 生成 anthraquinone-2-propaneacetal
  参考文献：
  名称：

  Synthesis and Properties of the First Highly Conjugated Tetrathiafulvalene Analogues Covalently Attached to [60]Fullerene

  摘要：

  The synthesis of the first C-60-based donor-acceptor (D-A) systems (12a-c) in which the C-60 core is covalently linked to strong, highly conjugated pi-electron donors derived of tetrathiafulvalene (TTF) with p-quinodimethane structure has been carried out by cyclization with azomethine ylides following Prate's procedure. The synthetic strategy requires the preparation of the novel formyl-substituted pi-extended donors which, in turn, are prepared in a multistep synthetic procedure by reaction of 2-formyl-9,10-anthraquinone (6) with the appropriately substituted phosphonate esters (8). Semiempirical PM3 calculations predict a geometry highly distorted from planarity for the donor fragment and a most stable conformation in which both 1,3-dithiole rings are far away from the [60]fullerene surface. The redox properties were determined by cyclic voltammetry in solution and reveal the presence of four cathodically shifted reduction waves, relative to C-60 and corresponding to the C-60 core, and a two-electron single oxidation wave to form stable dication species of the pi-extended donor units. Magnetic susceptibility measurements clearly indicate a paramagnetic behavior in the solid state, and a remarkable conductivity is observed for these single component organic compounds.

  DOI：

  10.1021/jo970320+

文献信息

• Double-spiro organic compounds and organic electroluminescent devices using the same
  申请人：LG Chem, Ltd.

  公开号：US06998487B2

  公开（公告）日：2006-02-14

  Disclosed are double-spiro organic compounds and an organic electroluminescence (EL) device using the same. The double-spiro organic compounds are configured to have at least three planar and substantially linear moieties, such that one planar moiety is located between two neighboring planar moieties and that the intervening planar moiety shares an atom with each of the two neighboring planar moieties. The double-spiro compounds generally have high melting point above about 300 degree C. and low crystallinity, which provide thermal stability to the organic EL devices. These organic compounds have good sublimability. They also have light-emitting, hole-injecting, hole-transporting, electron injection, electron-transporting properties and characteristics, which are favorable in the organic EL devices.

  揭示了双螺环有机化合物及其使用的有机电致发光（EL）器件。这些双螺环有机化合物被设计为至少具有三个平面且基本线性的基团，使得一个平面基团位于两个相邻的平面基团之间，并且介于两个相邻平面基团之间的中间基团与这两个相邻的平面基团中的每一个共享一个原子。双螺环化合物通常具有高于约300摄氏度的高熔点和低结晶度，这为有机EL器件提供了热稳定性。这些有机化合物具有良好的升华性能。它们还具有发光、注入正空穴、正空穴传输、注入电子、电子传输性能和特性，在有机EL器件中具有优势。
• Synthesis and Properties of the First Highly Conjugated Tetrathiafulvalene Analogues Covalently Attached to [60]Fullerene
  作者：Nazario Martín、Ignacio Pérez、Luis Sánchez、Carlos Seoane

  DOI：10.1021/jo970320+

  日期：1997.8.1

  The synthesis of the first C-60-based donor-acceptor (D-A) systems (12a-c) in which the C-60 core is covalently linked to strong, highly conjugated pi-electron donors derived of tetrathiafulvalene (TTF) with p-quinodimethane structure has been carried out by cyclization with azomethine ylides following Prate's procedure. The synthetic strategy requires the preparation of the novel formyl-substituted pi-extended donors which, in turn, are prepared in a multistep synthetic procedure by reaction of 2-formyl-9,10-anthraquinone (6) with the appropriately substituted phosphonate esters (8). Semiempirical PM3 calculations predict a geometry highly distorted from planarity for the donor fragment and a most stable conformation in which both 1,3-dithiole rings are far away from the [60]fullerene surface. The redox properties were determined by cyclic voltammetry in solution and reveal the presence of four cathodically shifted reduction waves, relative to C-60 and corresponding to the C-60 core, and a two-electron single oxidation wave to form stable dication species of the pi-extended donor units. Magnetic susceptibility measurements clearly indicate a paramagnetic behavior in the solid state, and a remarkable conductivity is observed for these single component organic compounds.