11,11,12,12-Tetracyano-1,4-anthraquinodimethane | 88068-06-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 11,11,12,12-Tetracyano-1,4-anthraquinodimethane
• 英文别名: Propanedinitrile, 2,2'-(1,4-anthracenediylidene)bis-；2-[4-(dicyanomethylidene)anthracen-1-ylidene]propanedinitrile
• CAS: 88068-06-8
• 化学式: C₂₀H₈N₄
• 分子量: 304.31
• InChiKey: AJEGMUBKEAENFH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  24
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  95.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  Cyano-[4-(cyano-ethoxycarbonyl-methyl)-anthracen-1-yl]-acetic acid ethyl ester 以5%的产率得到
  参考文献：
  名称：

  YAMAGUCHI, SHUNRO;TATEMITSU, HITOSHI;SAKATA, YOSHITERU;MISUMI, SOICHI, CHEM. LETT., 1983, N 8, 1229-1230

  摘要：

  DOI：

文献信息

• SYNTHESIS OF TWO ISOMERIC TETRACYANOANTHRAQUINODIMETHANES
  作者：Shunro Yamaguchi、Hitoshi Tatemitsu、Yoshiteru Sakata、Soichi Misumi

  DOI：10.1246/cl.1983.1229

  日期：1983.8.5

  Synthesis of two new acceptors, i.e., dibenzo- and naphtho-TCNQ, is described. Their redox potentials suggest that benzo and naphtho annelations to TCNQ lower the acceptor strength. Both compounds gave no CT complex with TTT, TTF, etc.

  描述了两种新受体的合成，即二苯并萘基-TCNQ。它们的氧化还原电位表明苯并和萘酚与 TCNQ 的退火降低了受体强度。两种化合物均不产生与 TTT、TTF 等的 CT 复合物。
• Synthesis and Characterization of 11,11,12,12-Tetracyano-1,4-anthraquinodimethanes (1,4-TCAQs): Novel Electron Acceptors with Photoinduced Charge-Transfer Properties
  作者：Nazario Martin、Jose L. Segura、Carlos Seoane、Pilar de la Cruz、Fernando Langa、Enrique Orti、Pedro M. Viruela、Rafael Viruela

  DOI：10.1021/jo00118a025

  日期：1995.6

  The synthesis of novel substituted 11,11,12,12-tetracyano-1,4-anthraquinodimethanes (1,4-TCAQs) 3 from the corresponding 1,4-anthraquinones 2 by reaction with the Lehnert's reagent is described, thus confirming the validity of this procedure to obtain different substitution patterns on the benzene fused quinone ring. W-vis spectra of the novel compounds show the presence of an intramolecular charge-transfer band in the blue part of the visible region. Depending upon the substitution pattern, the cyclic voltammetry (CV) measurements on 1,4-TCAQs reveal one reduction wave involving two electrons to the dianion or two One-electron reduction waves to the corresponding radical-anion and dianion. Acceptor properties similar to those of TCNQ are expected for 3 when the TCNQ moiety is substituted with chlorine atoms. The molecular and electronic structures of compounds 2 and 3 are investigated using the semiempirical PM3 method and the nonempirical VEH approach, respectively. PM3 calculations predict that 1,4-TCAQs are nonplanar and adopt a butterfly-type structure where the planarity of the lateral naphthalene unit is preserved. VEH calculations show that the naphthalene moiety behaves as an electron donor since the HOMO --> LUMO transition corresponds to an electronic charge transfer from this moiety to the acceptor TCNQ ring, thus supporting the experimental UV-vis results. The evolution of the geometric structure of compounds 3 upon reduction evidences a gain of aromaticity of the TCNQ ring, even if the anions are predicted to remain nonplanar. This absence of planarity justifies the low stability found experimentally for the anions and explains the observation of only one reduction wave involving two-electrons for the most hindered derivatives.
• YAMAGUCHI, SHUNRO;TATEMITSU, HITOSHI;SAKATA, YOSHITERU;MISUMI, SOICHI, CHEM. LETT., 1983, N 8, 1229-1230
  作者：YAMAGUCHI, SHUNRO、TATEMITSU, HITOSHI、SAKATA, YOSHITERU、MISUMI, SOICHI

  DOI：——

  日期：——