(meso-triphenyltetrabenzoporphinato)zinc(II) | 120389-74-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: (meso-triphenyltetrabenzoporphinato)zinc(II)
• 英文别名: Zn-5,10,15-triphenyl-tetrabenzoporphyrin；zinc(II) complex with triphenyltetrabenzoporphine；meso-triphenyltetrabenzoporphyrin zinc
• CAS: 120389-74-4
• 化学式: C₅₄H₃₂N₄Zn
• 分子量: 802.265
• InChiKey: XAZATBIWDLCHIV-MNZMCYINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  None
• 重原子数：
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• 可旋转键数：
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• 环数：
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• sp3杂化的碳原子比例：
  None
• 拓扑面积：
  None
• 氢给体数：
  None
• 氢受体数：
  None

反应信息

• 作为反应物：
  描述：

  (meso-triphenyltetrabenzoporphinato)zinc(II) 在 吡啶 、 N-溴代丁二酰亚胺(NBS) 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 5,10,15-(triphenyl),20-(bromo)tetrabenzoporphyrinate Zn(II)
  参考文献：
  名称：

  金属有机绿色染料：用于染料敏化太阳能电池的改性Zn-苯并卟啉的化学和物理洞察力†

  摘要：

  一种新的绿色不对称三苯基锌-四苯并卟啉锌化合物，即5,10,15-（三苯基），20- [乙炔基-（4-羧基）苯基]四苯并卟啉锌（II），已被合成为新的适用于染料敏化太阳能电池的染料。该分子显示出杂卟啉-酞菁杂化结构，通过在中间位置进行取代，可以对酞菁进行更精细的化学和物理性质调节，并显示出在456 nm处有很强的Soret谱带和可见光的UV-vis谱。在655 nm处可检测到的Q带。对分子的光物理和氧化还原特性进行了研究，结果表明，HOMO和LUMO能量值已正确定位以进行有效的电荷转移。基于DFT从头算起已经确认了前沿轨道的能量位置，并强调了可见光谱的复杂结构和被视为复杂设备一部分的分子的电荷转移行为。最终，实现了染料敏化太阳能电池，并测量了IPCE和光伏参数，初步效率约为2％。

  DOI：

  10.1039/c5ra20945e
• 作为产物：
  描述：

  triphenyltetrabenzoporphine 、 zinc diacetate 以 吡啶 为溶剂， 生成 (meso-triphenyltetrabenzoporphinato)zinc(II)
  参考文献：
  名称：

  Complex Formation and Spectral Properties of meso-Phenyltetrabenzoporphyrins in Pyridine and N,N-Dimethylformamide

  摘要：

  Contributions of structural (macroring distortion) and polarization (in asymmetrically substituted derivatives) effects into the reactivity and chromophoric properties of substituted porphyrins were revealed on the basis of the kinetics of complex formation of nona, deca-, undeca-, and dodecasubstituted porphyrins (meso-phenyltetrabenzoporphyrins) with Zn(OAc)(2) in pyridine and the electronic absorption spectra of the ligands and their complexes with Zn(II) and Cu(II) in pyridine and N,N-dimethylformamide (DMF). Dodecaphenyl substitution produces a weaker ring distortion in the more aromatic tetrabenzoporphyrin compared with porphyrins themselves. Irrespective of the degree of macroring nonplanarity, the Zn (11) and Cu complexes of tetrabenzoporphyrins with increasing degree of meso-phenyl substitution meet a spectral stability criterion.

  DOI：

  10.1023/b:rugc.0000007663.33757.32

文献信息

• Singlet oxygen generation by tetrabenzoporphyrins as photosensitizer
  作者：Madoka Yasuike、Tsuguo Yamaoka、Osamu Ohno、Masako Sakuragi、Kunihiro Ichimura

  DOI：10.1016/s0020-1693(00)85070-7

  日期：1991.6

  The efficiency of the photosensitized generation of singlet oxygen (O-1(2)) with meso-phenyl substituted tetrabenzoporphyrin metallo complexes as sensitizer was determined from the limiting quantum yield of the (+)-limonene photooxygenation and compared with that of hematoporphyrin (HP), which has been known to serve as an effective sensitizer, using a He-Ne laser light (633 mm). Among the diamagnetic (Mg, Zn, and Cd) complexes treated here, the Zn complexes were most efficient for the (+)-limonene photooxygenation with the limiting quantum yields of PHI(-A) = 0.4. This result was comparable to that of HP. The direct observation of the intensity of O-1(2) emission by the laser flash photolysis technique supported these results.
• Formation of tetrabenzoporphine skeleton by the reactions of phthalimide with zinc carbonates
  作者：Kunihiro Ichimura、Masako Sakuragi、Hisayuki Morii、Madoka Yasuike、Yasumasa Toba、Masaru Fukui、Osamu Ohno

  DOI：10.1016/s0020-1693(00)87937-2

  日期：1991.8

  The high temperature reactions of phthalimide potassium salt (PIK) with various zinc carbonates were carried out. The reaction of PIK with zinc acetate yielded tetrabenzoporphinato zinc (ZnTBP). Tetra-tert-butyltetrabenzoporphinato zinc (ZntBu4TBP), whose four tert-butyl substituents were positioned on the TBP periphery, was also prepared in a similar way using the 4-tert-butylphthalimide potassium salt (4-tBuPIK). These results were explained on the basis of the function of zinc acetate as the meso-methine carbon source of the TBP structure. The use of zinc phenylacetate instead of zinc acetate in the reaction of PIK led to the production of meso-phenyl substituted ZnTBPs, although they were different in the number of meso-phenyl substituent(s). The attempt to introduce alkyl residues at the meso-position(s) by the reaction of PIK in the presence of zinc alkylacetate having a long alkyl chain was not successful, except for the substitution of the methyl group using zinc propionate.
• Reinvestigation of synthetic methods for zinc meso-tetraphenyltetrabenzoporphyrin
  作者：Kunihiro Ichimura、Masako Sakuragi、Hisayuki Morii、Madoka Yasuike、Masaru Fukui、Osamu Ohno

  DOI：10.1016/s0020-1693(00)85087-2

  日期：1990.10
• ——
  作者：D. B. Berezin、O. V. Shukhto、N. E. Galanin

  DOI：10.1023/a:1025150018834

  日期：——

  Kinetic stability of zinc complexes with meso-phenyltetrabenzoporphyrins in DMSO-HOAc mixture and in glacial acetic acid was studied. The stability of complexes was found to decrease with reduction in their macrocyclic effect and with increasing polarization of their macrocycles. The stability of nonplanar and nonsymmetrically substituted complexes was determined to be lower than that of the more planar and symmetrically substituted complexes.
• ——
  作者：N. E. Galanin、E. V. Kudrik、G. P. Shaposhnikov

  DOI：10.1023/a:1020715202738

  日期：——

  meso-Monophenyltetrabenzoporphine and its zinc complex were synthesized starting from 3-(3-oxo-2,3-dihydro-1H-isoindol-1-yiidenemethyl)-1H-isoindol-1-one. The effect of unsymmetrical meso-substitution on physical and spectral properties of the products is discussed. The results of quantum-chemical calculations suggest spatial distortion of the porphyrin macroring.