6,7-dimethoxy-naphthalene-2,3-dicarbonitrile

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 6,7-dimethoxy-naphthalene-2,3-dicarbonitrile
• 英文别名: 6,7-Dimethoxynaphthalene-2,3-dicarbonitrile
• 化学式: C₁₄H₁₀N₂O₂
• 分子量: 238.246
• InChiKey: DUVJVONSIPUJHK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  66
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(2,4-dimethyl-3-pentyloxy)phthalonitrile 、 6,7-dimethoxy-naphthalene-2,3-dicarbonitrile 在 lithium 、 溶剂黄146 作用下， 生成
  参考文献：
  名称：

  Phthalonaphthalocyanines:  New Far-Red Dyes for Spectral Hole Burning

  摘要：

  Mixed phthalocyanines carrying one anthracene (Pc(3)An) or substituted naphthalene nucleus (Pc(3)NcR(2), R = H, OCH3, or SC12H25) are proposed as low-temperature photochroms for spectral hole burning. Solubility of these compounds in polymers was greatly enhanced by introducing the 2,4-dimethyl-3-pentoxy substituent to the remaining three benzopyrrolic fragments. The wavelengths and intensities of the Q transitions (S-1 and S-2) were measured for two prototropic tautomers having different position of the pair of inner protons. The average energy of the two lowest transitions is very similar in both tautomers, although the S-1-S-2 Splitting is much smaller in the less stable form. The relative equilibrium concentration of the tautomers at room temperature depends on the electron releasing properties of the substituents. This allows one to predict the positions of protons in each form. Absorption dichroism of stretched polyethylene films was used in order to establish the direction of the S-1 and S-2 transition dipole moments in the molecular framework. The tautomers can be completely converted into each other at 10 K by light with quantum yields of (1-2) x 10(-3) and (5-8) x 10(-3), respectively, depending on the direction of the process. Most probably the phototransformation occurs in the vibrationally relaxed triplet state via the tunneling of a single proton which results in an intermediate state with cis-configuration of protons. The photochemically accumulated less stable form decays at higher temperatures (T) as a result of a thermally activated tunneling process at characteristic T of 115 and 153 K for protonated and deuterated Pc(3)Nc, respectively. The strength of linear electron-photon coupling (EPC), which is crucial from the point of view of spectral hole burning, is characterized by Debye-Waller factors (DWFs) about 0.6-0.75, depending on the compound and the polymer matrix. The T dependence of quasihomogeneous hole width (T-qh) obeys a power law with coefficients 2.5 +/- 0.5 (between 6 and 30-45 K). In different polymer hosts, the DWF increases and the hole width decreases in the following order: polystyrene, poly(vinyl butyral) > polyethylene. The strength of EPC for the lowest transitions is similar in both tautomeric forms. A slight enhancement of the EPC strength in the series of dyes Pc(3)Nc(OCH3)(2) similar to Pc(3)Nc < Pc(3)Nc(SC12H25)(2) < Pc(3)An is correlated with the increase of electron-withdrawing power of substituents, plausibly, as a result of the increase of dipole moment change upon electronic excitation. Spectroscopic properties, phototautomerization quantum yields, and the EPC strength of mixed phthalocyanines were compared with those of chlorin and porphyrins.

  DOI：

  10.1021/jp971586n
• 作为产物：
  描述：

  4,5-dimethoxy-phthalaldehyde 、 反丁烯二腈 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙基膦 作用下， 以 二氯甲烷 为溶剂， 以80%的产率得到6,7-dimethoxy-naphthalene-2,3-dicarbonitrile
  参考文献：
  名称：

  Iterative synthesis of acenesvia homo-elongation

  摘要：

  从芳香邻二醛出发，我们设计了一套同系延长方案，结合了Wittig烯化反应和随后的分子内Knoevenagel缩合反应，以生成并五烷二酯和二腈。

  DOI：

  10.1039/b814840f

文献信息

• Nanoparticulate probe for in vivo monitoring of tissue oxygenation
  申请人：Kupussamy Periannan

  公开号：US20070041909A1

  公开（公告）日：2007-02-22

  A new class of micro- and nano-particulate paramagnetic spin probes useful for magnetic resonance imaging techniques, including electron paramagnetic resonance (EPR) and magnetic resonance imaging (MRI). The probes are lithium phthalocyanine derivative compounds. Also provided are suspensions and emulsions comprising lithium phthalocyanine derivative probes. Also provided are noninvasive methods for measuring noninvasive methods of measuring oxygen concentration, oxygen partial pressure, oxygen metabolism, and nitric oxide concentration in a specific tissue, organ, or cell in vivo or in vitro.
• NANOPARTICULATE PROBE FOR IN VIVO MONITORING OF TISSUE OXYGENATION
  申请人：The Ohio State University Research Foundation

  公开号：US20140170073A1

  公开（公告）日：2014-06-19

  A new class of micro- and nano-particulate paramagnetic spin probes especially useful for magnetic resonance imaging techniques, including electron paramagnetic resonance (EPR) and magnetic resonance imaging (MRI). The probes are lithium phthalocyanine derivative compounds. Also provided are suspensions and emulsions comprising lithium phthalocyanine derivative probes. Also provided are noninvasive methods for measuring noninvasive methods of measuring oxygen concentration, oxygen partial pressure, oxygen metabolism, and nitric oxide concentration in a specific tissue, organ, or cell in vivo or in vitro.
• US8066973B2
  申请人：——

  公开号：US8066973B2

  公开（公告）日：2011-11-29
• Iterative synthesis of acenesvia homo-elongation
  作者：Chih-Hsiu Lin、Ke-Han Lin、Bikash Pal、Li-Der Tsou

  DOI：10.1039/b814840f

  日期：——

  Starting from aromaticortho-dialdehydes, we devised a homo-elongation protocol that combines a Wittig olefination and subsequent intramolecular Knoevenagel condensation to produce acene diesters and dinitriles.

  从芳香邻二醛出发，我们设计了一套同系延长方案，结合了Wittig烯化反应和随后的分子内Knoevenagel缩合反应，以生成并五烷二酯和二腈。
• Phthalonaphthalocyanines:  New Far-Red Dyes for Spectral Hole Burning
  作者：Indrek Renge、Heinz Wolleb、Heinz Spahni、Urs P. Wild

  DOI：10.1021/jp971586n

  日期：1997.8.1

  Mixed phthalocyanines carrying one anthracene (Pc(3)An) or substituted naphthalene nucleus (Pc(3)NcR(2), R = H, OCH3, or SC12H25) are proposed as low-temperature photochroms for spectral hole burning. Solubility of these compounds in polymers was greatly enhanced by introducing the 2,4-dimethyl-3-pentoxy substituent to the remaining three benzopyrrolic fragments. The wavelengths and intensities of the Q transitions (S-1 and S-2) were measured for two prototropic tautomers having different position of the pair of inner protons. The average energy of the two lowest transitions is very similar in both tautomers, although the S-1-S-2 Splitting is much smaller in the less stable form. The relative equilibrium concentration of the tautomers at room temperature depends on the electron releasing properties of the substituents. This allows one to predict the positions of protons in each form. Absorption dichroism of stretched polyethylene films was used in order to establish the direction of the S-1 and S-2 transition dipole moments in the molecular framework. The tautomers can be completely converted into each other at 10 K by light with quantum yields of (1-2) x 10(-3) and (5-8) x 10(-3), respectively, depending on the direction of the process. Most probably the phototransformation occurs in the vibrationally relaxed triplet state via the tunneling of a single proton which results in an intermediate state with cis-configuration of protons. The photochemically accumulated less stable form decays at higher temperatures (T) as a result of a thermally activated tunneling process at characteristic T of 115 and 153 K for protonated and deuterated Pc(3)Nc, respectively. The strength of linear electron-photon coupling (EPC), which is crucial from the point of view of spectral hole burning, is characterized by Debye-Waller factors (DWFs) about 0.6-0.75, depending on the compound and the polymer matrix. The T dependence of quasihomogeneous hole width (T-qh) obeys a power law with coefficients 2.5 +/- 0.5 (between 6 and 30-45 K). In different polymer hosts, the DWF increases and the hole width decreases in the following order: polystyrene, poly(vinyl butyral) > polyethylene. The strength of EPC for the lowest transitions is similar in both tautomeric forms. A slight enhancement of the EPC strength in the series of dyes Pc(3)Nc(OCH3)(2) similar to Pc(3)Nc < Pc(3)Nc(SC12H25)(2) < Pc(3)An is correlated with the increase of electron-withdrawing power of substituents, plausibly, as a result of the increase of dipole moment change upon electronic excitation. Spectroscopic properties, phototautomerization quantum yields, and the EPC strength of mixed phthalocyanines were compared with those of chlorin and porphyrins.