1,4,8,11,15,18,22,25-octabutoxyphthalocyaninato-palladium(II) | 866952-93-4

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 1,4,8,11,15,18,22,25-octabutoxyphthalocyaninato-palladium(II)
• 英文别名: PdPc(OBu)8
• CAS: 866952-93-4
• 化学式: C₆₄H₈₀N₈O₈Pd
• 分子量: 1195.81
• InChiKey: HRPQQBPFMRDCOZ-UHFFFAOYSA-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：
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• 拓扑面积：
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• 氢给体数：
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• 氢受体数：
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反应信息

• 作为产物：
  描述：

  邻苯二酚 在 1,1'-双(二苯基膦)二茂铁 、 tris-(dibenzylideneacetone)dipalladium(0) 、 溴 、 potassium carbonate 作用下， 以 四氯化碳 、 N,N-二甲基乙酰胺 、 苯甲腈 、 丙酮 为溶剂， 生成 1,4,8,11,15,18,22,25-octabutoxyphthalocyaninato-palladium(II)
  参考文献：
  名称：

  八烷氧基钯和八苯氧基酞菁钯（II）：在Sonogashira反应中作为催化剂的合成和评估

  摘要：

  八烷氧基和八苯氧基取代的钯酞菁在Sonogashira反应中用作交叉偶联催化剂的新家族成员。首次表明，末端炔烃在室温下于Pd和Cu共催化下，在温和条件下与对位取代的芳基溴化物进行温和反应，得到相应的苯乙炔。该协议代表钯酞菁在Pd / Cu促进的Sonogashira反应中作为均相催化剂的用途。

  DOI：

  10.1016/j.jcat.2019.04.003

文献信息

• Near-Infrared-Emitting Phthalocyanines. A Combined Experimental and Density Functional Theory Study of the Structural, Optical, and Photophysical Properties of Pd(II) and Pt(II) α-Butoxyphthalocyanines
  作者：Alexandra V. Soldatova、Junhwan Kim、Corrado Rizzoli、Malcolm E. Kenney、Michael A. J. Rodgers、Angela Rosa、Giampaolo Ricciardi

  DOI：10.1021/ic102209q

  日期：2011.2.7

  The structural, optical, and photophysical properties of 1,4,8,11,15,18,22,25-octabutoxyphthalocyaninato-palladium-(II), PdPc(OBu)(8), and the newly synthesized platinum analogue PtPc(OBu)(8) are investigated combining X-ray crystallography, static and transient absorption spectroscopy, and relativistic zeroth-order regular approximation (ZORA) Density Functional Theory (DFT)/Time Dependent DFT (TDDFT) calculations where spin-orbit coupling (SOC) effects are explicitly considered. The results are compared to those previously reported for NiPc(OBu)(8) (J. Phys. Chem. A 2005, 109, 2078) in an effort to highlight the effect of the central metal on the structural and photophysical properties of the group 10 transition metal octabutoxyphthalocyanines. Different from the nickel analogue, PdPc(OBu)(8) and PtPc(OBu)(8) show a modest and irregular saddling distortion of the macrocycle, but share with the first member of the group similar UV-vis spectra, with the deep red and intense Q-band absorption experiencing a blue shift down the group, as observed in virtually all tetrapyrrolic complexes of this triad. The blue shift of the Q-band along the MPc(OBu)(8) (M = Ni, Pd, Pt) series is interpreted on the basis of the metal-induced electronic structure changes. Besides the intense deep red absorption, the title complexes exhibit a distinct near-infrared (NIR) absorption due to a transition to the double-group 1E (pi,pi(star)) state, which is dominated by the lowest single-group E-3 (pi,pi(star)) state. Unlike NiPc(OBu)(8), which is nonluminescent, PdPc(OBu)(8) and PtPc(OBu)(8) show both deep red fluorescence emission and NIR phosphorescence emission. Transient absorption experiments and relativistic spin orbit TDDFT calculations consistently indicate that fluorescence and phosphorescence emissions occur from the S-1(pi,pi(star)) and T-1(pi,pi star) states, respectively, the latter being directly populated from the former, and the triplet state decays directly to the S-0 surface (the triplet lifetime in deaerated benzene solution was 3.04 mu s for Pd and 0.55 mu s for Pt). Owing to their triplet properties, PdPc(OBu)(8) and PtPc(OBu)(8) have potential for use in photodynamic therapy (PDT) and are potential candidates for NIR light emitting diodes or NIR emitting probes.