dioctyl 4,5-dicyanophthalate | 950491-94-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: dioctyl 4,5-dicyanophthalate
• 英文别名: 4,5-di(octyloxycarbonyl)phthalonitrile；Dioctyl 4,5-dicyanobenzene-1,2-dicarboxylate；dioctyl 4,5-dicyanobenzene-1,2-dicarboxylate
• CAS: 950491-94-8
• 化学式: C₂₆H₃₆N₂O₄
• 分子量: 440.583
• InChiKey: CECGKHKBIDLVPY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  32
• 可旋转键数：
  18
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  100
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  dioctyl 4,5-dicyanophthalate 、 在 1,8-diazabicyclo[5.4.0]undec-7-ene 作用下， 以 further solvent(s) 为溶剂， 以82%的产率得到2,3,9,10,16,17,24,25-octakis(octyloxycarbonyl)phthalocyaninatocopper(II)
  参考文献：
  名称：

  2,3,9,10,16,17,24,25-十（辛氧基羰基）酞菁。合成，光谱和电化学特性。

  摘要：

  一系列三个新颖的2,3,9,10,16,17,24,25-辛基（辛氧基羰基）酞菁化合物M [Pc（COOC8H17）8]（M = 2H，Cu，Zn）（1-3）具有通过以邻二甲苯为原料，通过新开发的方法，以有机碱1,8-二氮杂双环[5.4.0] undec-7促进的4,5-二（辛氧基氧羰基）邻苯二甲腈的四环化合成合成。 -烯（DBU）在不存在和存在的金属盐（如M（acac）2.H2O（M = Cu，Zn））中于120摄氏度的正辛醇中存在。除元素分析外，这些新型的辛基（辛氧基氧羰基）-取代的酞菁化合物已通过一系列光谱方法表征。还通过循环伏安法（CV）和微分脉冲伏安法（DPV）方法研究了这些化合物的电化学。相对于H2Pc，化合物1的第一次氧化和第一次还原都朝着正方向移动，这表明附着在酞菁外围位置的辛氧基羰基的吸电子特性。通过使用密度泛函理论（DFT）方法的理论计算结果已合理地解释了周边辛基氧羰基取代对一系列酞菁1-3电化学的影响。

  DOI：

  10.1021/ic700517e
• 作为产物：
  描述：

  dioctyl 4,5-dichlorophthalate 、 氰化锌 在 1,1'-双(二苯基膦)二茂铁 、 tris-(dibenzylideneacetone)dipalladium(0) 锌 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 以74%的产率得到dioctyl 4,5-dicyanophthalate
  参考文献：
  名称：

  Ester-functionalized phthalonitriles and zinc phthalocyanines via palladium-catalyzed cyanation of 4,5-dichlorophthalates

  摘要：

  Dicyanophthalates 3 were synthesized via Pd-catalyzed two-fold cyanation of the corresponding 4,5-dichlorophthalates with Zn(CN)(2), Appropriate modification of reaction conditions allowed one-pot synthesis of the corresponding zinc phthalocyanines 7 bearing eight peripheral alkyl ester groups. Powder X-ray diffraction study of a mesogenic zinc phthalocyanine bearing branched alkyl substituents revealed a rare case of a transition between two columnar rectangular liquid crystalline mesophases with different symmetry. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.03.004

文献信息

• The first solution-processable n-type phthalocyaninato copper semiconductor: tuning the semiconducting nature via peripheral electron-withdrawing octyloxycarbonyl substituents
  作者：Pan Ma、Jinglan Kan、Yuexing Zhang、Chunhua Hang、Yongzhong Bian、Yanli Chen、Nagao Kobayshi、Jianzhuang Jiang

  DOI：10.1039/c1jm13082j

  日期：——

  A series of unsymmetrical phthalocyaninato copper complexes simultaneously incorporating electron-withdrawing and electron-donating substituents at the phthalocyanine periphery CuPc(15C5)[(COOC8H17)6]} (2), CuPc[(adj-15C5)2][(COOC8H17)4]} (3), CuPc[(opp-15C5)2][(COOC8H17)4]} (4), CuPc(15C5)3[(COOC8H17)2]} (5) were prepared and isolated. For comparative studies, symmetrical analogues including 2,3,9,10,16,17,24,25-octakis(octyloxycarbonyl)phthalocyaninato copper complex Cu[Pc(COOC8H17)8] (1) and 2,3,9,10,16,17,24,25-tetrakis(15-crown-5)phthalocyaninato copper complex Cu[Pc(15C5)4] (6) were also prepared. Their electrochemistry was studied by cyclic voltammetry (CV) and differential pulse voltammetry (DPV). With the help of a solution-based self-assembly process, these compounds were fabricated into organic field effect transistors (OFETs) with top contact configuration on hexamethyldisilazane (HMDS)-treated SiO2/Si substrate. In line with the electrochemical investigation results, a p-type OFET with a carrier mobility (for holes) of 0.06 cm2 V−1 s−1 was shown for Cu[Pc(15C5)4] (6) with electron-donating 15-crown-5 as the sole type of peripheral substituent. In contrast, n-type devices with a carrier mobility (for electrons) of 6.7 × 10−6–1.6 × 10−4 cm2 V−1 s−1 were achieved for 1–5 with electron-withdrawing octyloxycarbonyl substituents at the peripheral positions of phthalocyanine ring, indicating the significant effect of electron-withdrawing octyloxycarbonyl substituents on tuning the nature of phthalocyanine organic semiconductors. The present results represent the first example of solution-processed n-type phthalocyanine-based OFET devices.

  一系列不对称的邻苯二甲酰亚胺铜杂化物（phthalocyaninato copper complexes）同时在邻苯二甲酰亚胺周围引入了电子吸引和电子供给取代基，制备并分离了CuPc(15C5)[(COOC8H17)6]} (2)、CuPc[(adj-15C5)2][(COOC8H17)4]} (3)、CuPc[(opp-15C5)2][(COOC8H17)4]} (4)和CuPc(15C5)3[(COOC8H17)2]} (5)。为了进行比较研究，还制备了对称性类似物，包括2,3,9,10,16,17,24,25-八烷氧基羧基邻苯二甲酰亚胺铜杂化物Cu[Pc(COOC8H17)8] (1)和2,3,9,10,16,17,24,25-四烷氧基(15-冠-5)邻苯二甲酰亚胺铜杂化物Cu[Pc(15C5)4] (6)。通过循环伏安法（CV）和差分脉冲伏安法（DPV）研究了它们的电化学性质。借助于基于溶液的自组装过程，这些化合物被构建成在六甲基二硅氮烷（HMDS）处理的SiO2/Si基底上的顶接有机场效应晶体管（OFET）。根据电化学研究的结果，Cu[Pc(15C5)4] (6)表现出以电子供给型15-冠-5作为唯一的外围取代基的p型OFET，孔载流子迁移率为0.06 cm² V⁻¹ s⁻¹。相对而言，1-5的n型器件表现出电子载流子迁移率为6.7 × 10⁻⁶–1.6 × 10⁻⁴ cm² V⁻¹ s⁻¹，其外围位置的邻苯二甲酰亚胺环含有电子吸引的辛烷氧基羧基取代基，表明电子吸引型的辛烷氧基羧基取代基在调节邻苯二甲酰亚胺有机半导体性质方面具有显著影响。目前的结果代表了溶液处理的n型邻苯二甲酰亚胺基OFET器件的第一个例子。
• Ester-functionalized phthalonitriles and zinc phthalocyanines via palladium-catalyzed cyanation of 4,5-dichlorophthalates
  作者：Benoît Tylleman、Rafael Gómez-Aspe、Gabin Gbabode、Yves Henry Geerts、Sergey Sergeyev

  DOI：10.1016/j.tet.2008.03.004

  日期：2008.5

  Dicyanophthalates 3 were synthesized via Pd-catalyzed two-fold cyanation of the corresponding 4,5-dichlorophthalates with Zn(CN)(2), Appropriate modification of reaction conditions allowed one-pot synthesis of the corresponding zinc phthalocyanines 7 bearing eight peripheral alkyl ester groups. Powder X-ray diffraction study of a mesogenic zinc phthalocyanine bearing branched alkyl substituents revealed a rare case of a transition between two columnar rectangular liquid crystalline mesophases with different symmetry. (c) 2008 Elsevier Ltd. All rights reserved.
• 2,3,9,10,16,17,24,25-Octakis(octyloxycarbonyl)phthalocyanines. Synthesis, Spectroscopic, and Electrochemical Characteristics
  作者：Xueying Wang、Yuexing Zhang、Xuan Sun、Yongzhong Bian、Changqin Ma、Jianzhuang Jiang

  DOI：10.1021/ic700517e

  日期：2007.8.1

  (M = Cu, Zn) in n-octanol at 120 degrees C. In addition to elemental analysis, these novel octakis(octyloxycarbonyl)-substituted phthalocyanine compounds have been characterized by a series of spectroscopic methods. The electrochemistry of these compounds was also studied by cyclic voltammetry (CV) and differential pulse voltammetry (DPV) methods. A significant shift to the positive direction for both

  一系列三个新颖的2,3,9,10,16,17,24,25-辛基（辛氧基羰基）酞菁化合物M [Pc（COOC8H17）8]（M = 2H，Cu，Zn）（1-3）具有通过以邻二甲苯为原料，通过新开发的方法，以有机碱1,8-二氮杂双环[5.4.0] undec-7促进的4,5-二（辛氧基氧羰基）邻苯二甲腈的四环化合成合成。 -烯（DBU）在不存在和存在的金属盐（如M（acac）2.H2O（M = Cu，Zn））中于120摄氏度的正辛醇中存在。除元素分析外，这些新型的辛基（辛氧基氧羰基）-取代的酞菁化合物已通过一系列光谱方法表征。还通过循环伏安法（CV）和微分脉冲伏安法（DPV）方法研究了这些化合物的电化学。相对于H2Pc，化合物1的第一次氧化和第一次还原都朝着正方向移动，这表明附着在酞菁外围位置的辛氧基羰基的吸电子特性。通过使用密度泛函理论（DFT）方法的理论计算结果已合理地解释了周边辛基氧羰基取代对一系列酞菁1-3电化学的影响。