7-tert-butyl-1,2-dicyanonaphthalene | 134030-36-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 7-tert-butyl-1,2-dicyanonaphthalene
• 英文别名: 1,2-dicyano-7-tert-butylnaphthalene；7-Tert-butylnaphthalene-1,2-dicarbonitrile；7-tert-butylnaphthalene-1,2-dicarbonitrile
• CAS: 134030-36-7
• 化学式: C₁₆H₁₄N₂
• 分子量: 234.301
• InChiKey: XPQDONYMODBFDJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  7-tert-butyl-1,2-dicyanonaphthalene 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 五羰基铁 作用下， 以 various solvent(s) 为溶剂， 反应 2.0h， 生成 alkaline earth salt of/the/ methylsulfuric acid
  参考文献：
  名称：

  Synthesis and characterization of substituted (1,2-naphthalocyaninato)iron compounds and bisaxially coordinated isocyanide complexes

  摘要：

  Tetrasubstituted (1,2-naphthalocyaninato)iron(II) compounds t-Bu4-1,2-NcFe (13), Me4-1,2-NcFe (14), and Ph4-1,2-NcFe (15) are obtained from 7-substituted 1,2-dicyanonaphthalenes 12a-c either by reaction with pentacarbonyliron in 1-chloronapthalene (method a) or with iron(II) acetate in 1-hexanol (method b), respectively. Compounds 13-15 were characterized by UV/vis, IR, and Mossbauer spectroscopy, and the oxidation potentials, measured by cyclic voltammetry in pyridine, are compared with the oxidation potentials of 1,2-NcFe and PcFe. The substituted (1,2-naphthalocyaninato)iron compounds 13, 14, and 15 react with alkyl and aryl isocyanides R'NC (R' = t-Bu, c-Hx, Bz, Me2Ph), yielding the bisaxially coordinated isocyanide complexes of 13, 14, and 15, R4-1,2-NcFe (R'NC)2. Due to their comparatively high solubility in organic solvents, it is possible to characterize the isocyanide complexes with H-1 and C-13 NMR spectroscopy. The H-1 NMR spectra of, for example, t-Bu4-1,2-NcFe(t-BuNC)2 reveal that only one of the structural isomers of the unsymmetrical 1,2-naphthalocyanine macrocycle, namely, the 1,2-naphthalocyanine with C4h symmetry (see Figure 1) is formed, if the synthesis starting with 7-tert-butyl-1,2-dicyanonaphthalene (12a) is carried out according to method a. The crystal structure of the isomer obtained, t-Bu4-1,2-Nc(t-BuNC)2, is determined (Figure 4) and confirms these findings. All isocyanide complexes R4-1,2-NcFe(R'NC)2 are characterized by spectral data and thermoanalyses. The reaction of R4-1,2-NcFe 13, 14, and 15 with diisocyanobenzene (dib) leads to the bridged compounds [R4-1,2-NcFe(dib)]n, R = t-Bu, Me, Ph. After being doped with iodine, the bridged complexes exhibit good semiconducting properties.

  DOI：

  10.1021/jo00011a012
• 作为产物：
  描述：

  7-tert-butyl-3,4-dihydronaphthalene-1,2-dicarboxycyclic acid anhydride 在 吡啶 、 氢氧化钾 、 氯化亚砜 、 硫酸 、 氨 、 N,N-二甲基甲酰胺 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 三氯氧磷 作用下， 以 乙醚 、 乙醇 、 氯仿 、 水 、 甲苯 为溶剂， 反应 117.0h， 生成 7-tert-butyl-1,2-dicyanonaphthalene
  参考文献：
  名称：

  Synthesis and characterization of substituted (1,2-naphthalocyaninato)iron compounds and bisaxially coordinated isocyanide complexes

  摘要：

  Tetrasubstituted (1,2-naphthalocyaninato)iron(II) compounds t-Bu4-1,2-NcFe (13), Me4-1,2-NcFe (14), and Ph4-1,2-NcFe (15) are obtained from 7-substituted 1,2-dicyanonaphthalenes 12a-c either by reaction with pentacarbonyliron in 1-chloronapthalene (method a) or with iron(II) acetate in 1-hexanol (method b), respectively. Compounds 13-15 were characterized by UV/vis, IR, and Mossbauer spectroscopy, and the oxidation potentials, measured by cyclic voltammetry in pyridine, are compared with the oxidation potentials of 1,2-NcFe and PcFe. The substituted (1,2-naphthalocyaninato)iron compounds 13, 14, and 15 react with alkyl and aryl isocyanides R'NC (R' = t-Bu, c-Hx, Bz, Me2Ph), yielding the bisaxially coordinated isocyanide complexes of 13, 14, and 15, R4-1,2-NcFe (R'NC)2. Due to their comparatively high solubility in organic solvents, it is possible to characterize the isocyanide complexes with H-1 and C-13 NMR spectroscopy. The H-1 NMR spectra of, for example, t-Bu4-1,2-NcFe(t-BuNC)2 reveal that only one of the structural isomers of the unsymmetrical 1,2-naphthalocyanine macrocycle, namely, the 1,2-naphthalocyanine with C4h symmetry (see Figure 1) is formed, if the synthesis starting with 7-tert-butyl-1,2-dicyanonaphthalene (12a) is carried out according to method a. The crystal structure of the isomer obtained, t-Bu4-1,2-Nc(t-BuNC)2, is determined (Figure 4) and confirms these findings. All isocyanide complexes R4-1,2-NcFe(R'NC)2 are characterized by spectral data and thermoanalyses. The reaction of R4-1,2-NcFe 13, 14, and 15 with diisocyanobenzene (dib) leads to the bridged compounds [R4-1,2-NcFe(dib)]n, R = t-Bu, Me, Ph. After being doped with iodine, the bridged complexes exhibit good semiconducting properties.

  DOI：

  10.1021/jo00011a012

文献信息

• Study of Substituent Effects on the Photoconductivity of Soluble 2,(3)- and 1,(4)-Substituted Phthalocyaninato- and Naphthalocyaninatotitanium(IV) Oxides
  作者：Götz Winter、Heino Heckmann、Peter Haisch、Wolfgang Eberhardt、Michael Hanack、Larry Lüer、Hans-Joachim Egelhaaf、Dieter Oelkrug

  DOI：10.1021/ja981644y

  日期：1998.11.1

  Soluble alkyl (II, 8a,b), fluoroalkyl,(4a), and fluoroalkoxy (4b,c, 8c) 1,(4)- or 2,(3)-substituted phthalocyaninato- and linear 2,(3)- and-angular 1,(2)-annulated naphthalocyaninatotitanium(IV) oxides 10, 12, and 14 were synthesized and characterized with regard to their spectroscopic, photophysical, and photochemical properties. While alkyl- and fluoroalkoxy-substituted compounds are highly soluble in nonpolar solvents, e.g., hexane, fluoroalkyl-substituted compounds are better soluble in polar aprotic solvents such as acetone. The stability against photooxidation in solution is' enhanced on going-from alkylated phthalocyanines 1,(4)-(C(5)H(11))(8)PcTiO (8a), 1,(4)-(C(6)H(13))(8)PcTiO (4b), and 2,(3)-(C(4)H(9))(8)PcTiO (II) to fluorinated phthalocyanines 2,(3)-(CF(3))(4)PcTiO (4a), 2,(3)-(CF(3)CH(2)O)(4)PcTiO (4b), and 2,(3)-(CF(3)CH(2)O)(8)PcTiO (4c), from phthalocyanines to naphthalocyanines (tert-butyl)(4)-2,(3)-NcTiO (10), 1,(2)-NcTiO (12), and (tert-butyl)(4)-1,(2)-NdTiO (14), and on going from 2,(3)-substituted 4a-c to 1,(4)-substituted phthalocyanines 8a-c. Thin films of these compounds, prepared by either vacuum deposition or spin casting, are classified into three types according to increasing intermolecular pi-pi interactions. Type alpha films, characterized:by absence of exciton splitting, are formed from 1,(4)-substituted phthalocyanines 8a-c. These films show low dark conductivities and photoconductivities and are considerably sensitive to photooxidation. Type beta films, characterized by weak exciton splitting, are formed from fluorinated phthalocyanines 4a-c as well as from rapidly deposited 2,(3)-substituted phthalocyanines II and the unsubstituted PcTiO (I). These films show enhanced photoconductivity and are generally more stable against photooxidation than type alpha films. Type gamma films, formed by slow deposition of II, 10 and unsubstituted phthalocyanine I, are classified by a largely red-shifted B-band absorbing in the near-IR. These films are highly photosensitive as well as stabilized against photooxidation. Steady-state photoconductivities and dark conductivities in thin films are strongly dependent on oxygen partial pressure. Alkylated PcTiO's such as 8a, 8b, and II are found to be p-type conductors (positive oxygen influence on conductivities) like unsubstituted PcTiO (I), whereas angularly annulated naphthalocyanines such as 12 and 14 as well as fluorinated PcTiO's 4a-c are n-type conductors (negative oxygen influence on conductivity). These findings are rationalized by comparison with experimental and theoretical literature data.
• Synthesis and characterization of substituted (1,2-naphthalocyaninato)iron compounds and bisaxially coordinated isocyanide complexes
  作者：Michael Hanack、Guenter Renz、Joachim Straehle、Siegbert Schmid

  DOI：10.1021/jo00011a012

  日期：1991.5

  Tetrasubstituted (1,2-naphthalocyaninato)iron(II) compounds t-Bu4-1,2-NcFe (13), Me4-1,2-NcFe (14), and Ph4-1,2-NcFe (15) are obtained from 7-substituted 1,2-dicyanonaphthalenes 12a-c either by reaction with pentacarbonyliron in 1-chloronapthalene (method a) or with iron(II) acetate in 1-hexanol (method b), respectively. Compounds 13-15 were characterized by UV/vis, IR, and Mossbauer spectroscopy, and the oxidation potentials, measured by cyclic voltammetry in pyridine, are compared with the oxidation potentials of 1,2-NcFe and PcFe. The substituted (1,2-naphthalocyaninato)iron compounds 13, 14, and 15 react with alkyl and aryl isocyanides R'NC (R' = t-Bu, c-Hx, Bz, Me2Ph), yielding the bisaxially coordinated isocyanide complexes of 13, 14, and 15, R4-1,2-NcFe (R'NC)2. Due to their comparatively high solubility in organic solvents, it is possible to characterize the isocyanide complexes with H-1 and C-13 NMR spectroscopy. The H-1 NMR spectra of, for example, t-Bu4-1,2-NcFe(t-BuNC)2 reveal that only one of the structural isomers of the unsymmetrical 1,2-naphthalocyanine macrocycle, namely, the 1,2-naphthalocyanine with C4h symmetry (see Figure 1) is formed, if the synthesis starting with 7-tert-butyl-1,2-dicyanonaphthalene (12a) is carried out according to method a. The crystal structure of the isomer obtained, t-Bu4-1,2-Nc(t-BuNC)2, is determined (Figure 4) and confirms these findings. All isocyanide complexes R4-1,2-NcFe(R'NC)2 are characterized by spectral data and thermoanalyses. The reaction of R4-1,2-NcFe 13, 14, and 15 with diisocyanobenzene (dib) leads to the bridged compounds [R4-1,2-NcFe(dib)]n, R = t-Bu, Me, Ph. After being doped with iodine, the bridged complexes exhibit good semiconducting properties.