4,5-di(4-benzyloxyphenoxy)phthalonitrile | 934464-91-2

• 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: 4,5-di(4-benzyloxyphenoxy)phthalonitrile
• 英文别名: 4,5-bis-(benzyloxyphenoxy)-phthalonitrile；4,5-bis(4-benzyloxyphenoxy)phthalonitrile；1,2-bis(benzyloxyphenoxy)-4,5-dicyanobenzene；1,2-bis(4-benzyloxyphenoxy)-4,5-dicyanobenzene；4,5-bis(4-phenylmethoxyphenoxy)benzene-1,2-dicarbonitrile
• CAS: 934464-91-2
• 化学式: C₃₄H₂₄N₂O₄
• 分子量: 524.576
• InChiKey: XZNFWPKRNJDBCB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  40
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  84.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4,5-di(4-benzyloxyphenoxy)phthalonitrile 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 nickel dichloride 作用下， 以 戊醇 为溶剂， 反应 8.0h， 以74%的产率得到(2,3,9,10,16,17,23,24-octakis(4-benzyloxyphenoxy)phthalocyaninato)nickel(II)
  参考文献：
  名称：

  Photophysical and photochemical properties of Ni(II), Pd(II) and Pt(II) aryloxo and alkylthio derivatised phthalocyanine

  摘要：

  Several aryloxo (3a-6a and 3b-6b) and alkylthio (3d and 3e) derivatised phthalocyanines were synthesized, characterized and the photochemical and photophysical properties investigated along with those of the previously reported (3c-5c, 4d, 5d, 4e and 5e) complexes. The effects of open-shell metals (Ni(II), Pd(II) and Pt(II)) on the photophysical and photochemical properties of the phthalocyanine ligands were investigated. Palladium and platinum improved the triplet quantum yield and singlet oxygen generation capacities of the unmetalated phthalocyanines (3a-3e) making their complexes candidates for further investigation in photocatalysis. Ni(II)Pc analogues gave poor results compared with their Pd(II)Pc and Pt(II)Pc counterparts. (C) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2010.03.047
• 作为产物：
  描述：

  4-苄氧基苯酚 、 4-溴-5-硝基-1,2-苯二甲腈 在 potassium carbonate 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以52%的产率得到4,5-di(4-benzyloxyphenoxy)phthalonitrile
  参考文献：
  名称：

  苯氧基取代酞菁配体镁配合物的合成及发光性能

  摘要：

  摘要- 通过用苯酚衍生物的片段对硝基/溴原子进行亲核取代，已经获得了许多具有规则变化的外围苯氧基取代基的邻苯二甲腈。以这些邻苯二甲腈为基础，合成了具有多种结构的酞菁配体的镁络合物。对于此类配合物，在考虑各种溶剂中的光谱和荧光参数时，已经确定了取代基的性质、位置和数量的作用。结果表明，对于所研究的金属酞菁，其光谱特性在很大程度上受取代基位置的影响，而荧光量子产率的值则受上述所有特性的影响。

  DOI：

  10.1134/s0036023622030044

文献信息

• Synthesis, photophysical and photochemical properties of tetra- and octa-substituted gallium and indium phthalocyanines
  作者：Mahmut Durmuş、Tebello Nyokong

  DOI：10.1016/j.poly.2007.03.007

  日期：2007.8

  Abstract The synthesis, photophysical and photochemical properties of the tetra- and octa-[4-(benzyloxyphenoxy)] substituted gallium(III) and indium(III) phthalocyanines are reported for the first time. The new compounds have been characterized by elemental analysis, IR, 1H NMR spectroscopy and electronic spectroscopy. General trends are described for quantum yields of photodegredation, fluorescence

  摘要首次报道了四-和八-[4-（苄氧基苯氧基）]取代的镓（III）和铟（III）酞菁的合成，光物理和光化学性质。这些新化合物已通过元素分析，IR，1H NMR光谱和电子光谱进行了表征。描述了光降解的量子产率，荧光量子产率和寿命，三重态寿命和三重态量子产率以及这些化合物在二甲亚砜（DMSO）中的单重态氧量子产率的一般趋势。与取代的GaPc衍生物相比，取代的铟酞菁配合物（7b–9b）显示出更高的三重态量子产率，并且三重态寿命更短，这是由于前者的系统间交叉（ISC）增强。镓和铟酞菁配合物由于环还原而在激光辐照期间显示出光转化。单线态氧的量子产率（ΦΔ）表明该络合物在需要单线态氧（II型机理）的应用中作为光敏剂的潜力为0.51至0.94。因此，这些复合物显示出作为癌症的光动力疗法的潜力。
• Electrochemical characterisation of tetra- and octa-substituted oxo(phthalocyaninato)titanium(IV) complexes
  作者：Prudence Tau、Tebello Nyokong

  DOI：10.1016/j.electacta.2006.10.023

  日期：2007.3

  electrochemical characterisation of the following oxotitanium tetra-substituted phthalocyanines are reported: 1,(4)-(tetrabenzyloxyphthalocyaninato)titanium(IV) oxide (5a); 1,(4)-tetrakis[4-(benzyloxy)phenoxy]phthalocyaninato}titanium(IV) oxide (5b); 2,(3)-(tetrabenzyloxyphthalocyaninato)titanium(IV) oxide (6a) and 2,(3)-tetrakis[4-(benzyloxy)phenoxy]phthalocyaninato}titanium(IV) oxide (6b). The electrochemical

  报道了以下氧钛四取代的酞菁的合成和电化学表征：1，（4）-（四苄氧基酞菁萘）钛（IV）氧化物（5a）；1，（4）-四[4-（苄氧基）苯氧基]邻苯二甲酰氰基}氧化钛（IV）（5b）; 2，（3）-（四苄氧基邻苯二甲氧基酞菁钛）氧化物（6a）和2，（3）-四[4-（苄氧基）苯氧基]邻苯二甲酰氧基钛酞菁}（6b）。复合物的电化学表征辛取代4-（苄氧基）苯氧基（图9b），苯氧基（9C）和叔丁基苯氧基（9D）组也已报告。配合物的循环伏安图显示出可逆的偶对I – III，偶对IV对配合物5a，5b，6a和6b是准可逆的。前两次还原是基于金属的过程，通过光谱电化学证实是由于Ti IV Pc 2- / Ti III Pc 2-和Ti III Pc 2- / Ti II Pc 2-的氧化还原过程，最后两个还原是环- Ti II Pc 2- / Ti导致的基于过程的过程II Pc 3−和Ti II Pc 3−
• Synthesis, photophysical and nonlinear optical properties of microwave synthesized 4-tetra and octa-substituted lead phthalocyanines
  作者：Desmond Kwena Modibane、Tebello Nyokong

  DOI：10.1016/j.poly.2009.03.013

  日期：2009.6

  This work presents the photophysical and nonlinear optical behaviour of newly synthesized complexes: 2,(3)-tetrakis(4-benzyloxyphenoxyphthalocyaninato) lead (5a) and 2,3-octakis(4-benzyloxyphenoxyphthalocyaninato) lead (6a). The nonlinear optical behaviour of complexes 5a and 6a are compared with those of 2,(3)-tetraphenoxyphthalocyaninato lead (5b), 2,(3)-tetrakis(4-t-butylphenoxyphthalocyaninato) lead (5c), 2,3-octaphenoxyphthalocyaninato lead (6b) and 2,3-octakis(4-t-butylphenoxyphthalocyaninato) lead (6c). The synthesis of 5a and 6a was performed using microwave irradiation. Photophysical properties were studied for these complexes in dimethylsulfoxide, dimethylformamide, toluene, tetrahydrofuran and chloroform. The fluorescence spectra were different from excitation spectra due to demetallation upon excitation. High triplet quantum yields ranging from 0.80 to 0.86 (in DMSO, DMF and toluene) and low triplet lifetimes (20-50 mu s in DMSO, and < 10 mu s in the rest of the solvents) were observed due to the presence of heavy atom. Nonlinear optical properties were studied in dimethylsulfoxide. The optical limiting threshold intensity (I-lim) for the PbPc derivatives were calculated and ranged from 2.1 to 6.6 W/cm(2). (C) 2009 Elsevier Ltd. All rights reserved.
• Synthesis and solvent effects on the electronic absorption and fluorescence spectral properties of substituted zinc phthalocyanines
  作者：Mahmut Durmuş、Tebello Nyokong

  DOI：10.1016/j.poly.2007.01.018

  日期：2007.7

  The synthesis and spectroscopic properties of the following tetra- and octa-substituted aryloxy zinc(Il) phthalocyanines are reported for the first time: 1,(4)-(tetrabenzyloxyphenoxyphthalocyaninato) zinc(II) (7); 2,(3)-(tetrabenzyloxyphenoxyphthalocyaninato) zinc(II) (8); 2,3-(octabenzyloxyphenoxyphthalocyaninato) zinc(Il) (9). The new compounds have been characterized by elemental analysis, IR, 1H NMR spectroscopy and electronic spectroscopy. Spectroscopic properties of these compounds were investigated in different solvents. Protonation of non-peripherally substituted complex 7 resulted in the splitting and red-shifting of the Q-band. The peripherally substituted derivatives 8 and 9, did not show the split in the Q-band. Fluorescence spectra of the derivatives show Stokes shifts typical of MPc complexes. (C) 2007 Elsevier Ltd. All rights reserved.