2,3-dicyanotriptycene | 88456-63-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 2,3-dicyanotriptycene
• 英文别名: 2,3-dicyanotryptycene；2,3-dicyanotripticene；{5,10-[1,2]benzeno}-7,8-dicyano-5,10-dihydroanthracene；9,10[1',2']Benzenoanthracene-2,3-carbonitrile, 9,10-dihydro-；pentacyclo[6.6.6.02,7.09,14.015,20]icosa-2(7),3,5,9,11,13,15,17,19-nonaene-4,5-dicarbonitrile
• CAS: 88456-63-7
• 化学式: C₂₂H₁₂N₂
• 分子量: 304.351
• InChiKey: PJTVVOXJBUJBDE-UHFFFAOYSA-N

物化性质

• 熔点：
  269-272 °C
• 沸点：
  475.7±45.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  24
• 可旋转键数：
  0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  47.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,3-dicyanotriptycene 在 ammonium molybdate magnesium sulfate 、 sodium sulfate 、 尿素 作用下， 反应 2.0h， 以30%的产率得到tetra-2,3-tryptycenoporphyrazine
  参考文献：
  名称：

  Gal'pern, M. G.; Shalaev, V. K.; Shatsskaya, T. A., Journal of general chemistry of the USSR, 1983, vol. 53, # 11, p. 2346 - 2351

  摘要：

  DOI：
• 作为产物：
  描述：

  蒽 在 N-甲基吡咯烷酮 、 马来酸酐 、 亚硝酸异戊酯 作用下， 反应 9.0h， 生成 2,3-dicyanotriptycene
  参考文献：
  名称：

  Gal'pern, M. G.; Shalaev, V. K.; Shatsskaya, T. A., Journal of general chemistry of the USSR, 1983, vol. 53, # 11, p. 2346 - 2351

  摘要：

  DOI：

文献信息

• Iptycene-Derived Pyridazines and Phthalazines
  作者：Jean Bouffard、Robert F. Eaton、Peter Müller、Timothy M. Swager

  DOI：10.1021/jo702000d

  日期：2007.12.1

  The synthesis of new heterocyclic oligo(phenylene) analogues based on soluble, nonaggregating 1,2-diazines is reported. Improved palladium-catalyzed reductive coupling methods were developed to allow for the preparation of large quantities of iptycene-derived bipyridazines and biphthalazines, and the controlled synthesis of well-defined oligomers up to sexipyridazine. Crystallographic, spectroscopic, and computational evidence indicate that in these analogues, hindrance at the ortho position is relaxed relative to poly(phenylenes). The resulting building blocks are promising for incorporation in conjugated electronics materials, and as new iptycene-derived ligands for transition metals.
• Gal'pern, M. G.; Donyagina, V. F.; Shalaev, V. K., Journal of general chemistry of the USSR, 1982, vol. 52, # 3, p. 622 - 623
  作者：Gal'pern, M. G.、Donyagina, V. F.、Shalaev, V. K.、Skvarchenko, V. R.、Bundina, N. I.、at al.

  DOI：——

  日期：——
• Gal'pern, M. G.; Donyagina, V. F.; Shalaev, V. K., Journal of general chemistry of the USSR, 1982, vol. 52, p. 622 - 623
  作者：Gal'pern, M. G.、Donyagina, V. F.、Shalaev, V. K.、Skvarchenko, V. R.、Bundina, V. I.、et al.

  DOI：——

  日期：——
• Gal'pern, M. G.; Shalaev, V. K.; Shatsskaya, T. A., Journal of general chemistry of the USSR, 1983, vol. 53, p. 2346 - 2351
  作者：Gal'pern, M. G.、Shalaev, V. K.、Shatsskaya, T. A.、Shishkanova, L. S.、Skvarchenko, V. R.、Luk'yanets, E. A.

  DOI：——

  日期：——
• Novel Zinc Phthalocyanine-Benzoquinone Rigid Dyad and Its Photoinduced Electron Transfer Properties
  作者：Chi-Hang Lee、Jiangchang Guo、Lin X. Chen、Braja. K. Mandal

  DOI：10.1021/jo801293s

  日期：2008.11.7

  While preparing the first structurally rigid zinc phthalocyanine-benzoquinone (ZnPc-BQ) dyad as a model for photoinduced charge separation mimicking natural photosynthesis, a convenient method is developed for in situ generation of a benzoquinone chromophore in the dyad using an iso-butyryl mask. The dyad has no rotamers and possesses a fixed distance between ZnPc and BQ moieties (center-to-center and edge-to-edge distances are 9.40 and 2.14 angstrom, respectively). The dyad displays unusual electronic perturbation in the ground state, resulting from the interactions between Pc and BQ, and exhibits photoinduced electron transfer with a lifetime of 40 ps of the charged separated states. The steady-state fluorescence and electrochemical behavior of the dyad are evaluated. This study opens a route to subsequent dyads, triads, and complex architectures of electron donor-acceptor arrays with rigid structures and long charge separation states.