2,2'-oxydianthraquinone | 187729-11-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 2,2'-oxydianthraquinone
• 英文别名: 2,2'-Oxy-di-anthrachinon；2,2'-Oxydianthracene-9,10-dione；2-(9,10-dioxoanthracen-2-yl)oxyanthracene-9,10-dione
• CAS: 187729-11-9
• 化学式: C₂₈H₁₄O₅
• 分子量: 430.416
• InChiKey: NNAJBFBCXBFPTD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  33
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  77.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  二(三甲基硅基)碳酰二亚胺 、 2,2'-oxydianthraquinone 在 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以28%的产率得到2,2'-oxybis(N,N'-dicyano-9,10-anthraquinonediimine)
  参考文献：
  名称：

  Highly Conjugated π-Electron Donor and π-Electron Acceptor Dimers with p-Quinodimethane Structures

  摘要：

  The syntheses of the first dimeric donors (19a-c) derived from TTF with p-quinodimethane structures as well as the analogues dimeric accepters (20, 21) derived from TCNQ and DCNQI have been carried out from the novel 2,2'-oxydianthraquinone (18). Depending upon the substitution pattern on the 1,3-dithiole ring of the donor molecules, eight (19a) or sixteen (19b and 19c) sulfur atoms are contained in these dimers. The presence of the oxygen atom connecting both monomeric units has an influence on the redox properties of the novel dimers due to its electron-withdrawing effect. The CV data indicate that these dimers behave electrochemically as two independent monomers. This behavior de tines rather unusual electrochemical properties in both donor (19a-c) and acceptor (20) molecules, which exhibit only one redox wave involving a four-electron overall process. In contrast, the dimeric DCNQI derivative (21) showed two-electron reduction waves to form, simultaneously in both monameric units, the radical anions and dianions. The redox potential values show that although the dimeric accepters 20 and 21 exhibit too negative potentials to form stable solid CT-complexes with donor molecules, the novel dimeric donors show a donating ability similar to that of BEDT-TTF. The dimeric donors (19a-c) did not form CT-complexes with TCNQ and DCNQI due to their distorted structures, but they form CT-complexes with stronger acceptor molecules such as TCNQF(4) and DDQ. These CT-complexes, which showed in all cases a 1:3 (donor:acceptor) stoichiometry, exhibit a paramagnetic and semiconducting electrical behavior.

  DOI：

  10.1021/jo961795o
• 作为产物：
  描述：

  4,4'-oxybis(2-benzoylbenzoic acid) 在 PPA 作用下， 反应 24.0h， 以66%的产率得到2,2'-oxydianthraquinone
  参考文献：
  名称：

  Highly Conjugated π-Electron Donor and π-Electron Acceptor Dimers with p-Quinodimethane Structures

  摘要：

  The syntheses of the first dimeric donors (19a-c) derived from TTF with p-quinodimethane structures as well as the analogues dimeric accepters (20, 21) derived from TCNQ and DCNQI have been carried out from the novel 2,2'-oxydianthraquinone (18). Depending upon the substitution pattern on the 1,3-dithiole ring of the donor molecules, eight (19a) or sixteen (19b and 19c) sulfur atoms are contained in these dimers. The presence of the oxygen atom connecting both monomeric units has an influence on the redox properties of the novel dimers due to its electron-withdrawing effect. The CV data indicate that these dimers behave electrochemically as two independent monomers. This behavior de tines rather unusual electrochemical properties in both donor (19a-c) and acceptor (20) molecules, which exhibit only one redox wave involving a four-electron overall process. In contrast, the dimeric DCNQI derivative (21) showed two-electron reduction waves to form, simultaneously in both monameric units, the radical anions and dianions. The redox potential values show that although the dimeric accepters 20 and 21 exhibit too negative potentials to form stable solid CT-complexes with donor molecules, the novel dimeric donors show a donating ability similar to that of BEDT-TTF. The dimeric donors (19a-c) did not form CT-complexes with TCNQ and DCNQI due to their distorted structures, but they form CT-complexes with stronger acceptor molecules such as TCNQF(4) and DDQ. These CT-complexes, which showed in all cases a 1:3 (donor:acceptor) stoichiometry, exhibit a paramagnetic and semiconducting electrical behavior.

  DOI：

  10.1021/jo961795o

文献信息

• Perkin; Sewell, Journal of the Chemical Society, 1923, vol. 123, p. 3038
  作者：Perkin、Sewell

  DOI：——

  日期：——
• US4677155A
  申请人：——

  公开号：US4677155A

  公开（公告）日：1987-06-30
• US4797347A
  申请人：——

  公开号：US4797347A

  公开（公告）日：1989-01-10
• Highly Conjugated π-Electron Donor and π-Electron Acceptor Dimers with <i>p</i>-Quinodimethane Structures
  作者：Nazario Martín、Ignacio Pérez、Luis Sánchez、Carlos Seoane

  DOI：10.1021/jo961795o

  日期：1997.2.1

  The syntheses of the first dimeric donors (19a-c) derived from TTF with p-quinodimethane structures as well as the analogues dimeric accepters (20, 21) derived from TCNQ and DCNQI have been carried out from the novel 2,2'-oxydianthraquinone (18). Depending upon the substitution pattern on the 1,3-dithiole ring of the donor molecules, eight (19a) or sixteen (19b and 19c) sulfur atoms are contained in these dimers. The presence of the oxygen atom connecting both monomeric units has an influence on the redox properties of the novel dimers due to its electron-withdrawing effect. The CV data indicate that these dimers behave electrochemically as two independent monomers. This behavior de tines rather unusual electrochemical properties in both donor (19a-c) and acceptor (20) molecules, which exhibit only one redox wave involving a four-electron overall process. In contrast, the dimeric DCNQI derivative (21) showed two-electron reduction waves to form, simultaneously in both monameric units, the radical anions and dianions. The redox potential values show that although the dimeric accepters 20 and 21 exhibit too negative potentials to form stable solid CT-complexes with donor molecules, the novel dimeric donors show a donating ability similar to that of BEDT-TTF. The dimeric donors (19a-c) did not form CT-complexes with TCNQ and DCNQI due to their distorted structures, but they form CT-complexes with stronger acceptor molecules such as TCNQF(4) and DDQ. These CT-complexes, which showed in all cases a 1:3 (donor:acceptor) stoichiometry, exhibit a paramagnetic and semiconducting electrical behavior.