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首页> 外文期刊>Chemistry: A European journal >Stepwise Conversion of Two Pyrrole Moieties of Octaethylporphyrin to Pyridin-3-ones: Synthesis, Mass Spectral, and Photophysical Properties of Mono and BisACHTUNGTRENUNG(oxypyri)porphyrins
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Stepwise Conversion of Two Pyrrole Moieties of Octaethylporphyrin to Pyridin-3-ones: Synthesis, Mass Spectral, and Photophysical Properties of Mono and BisACHTUNGTRENUNG(oxypyri)porphyrins

机译：八乙基卟啉的两个吡咯部分向吡啶-3-酮的逐步转化：单和双邻苯并氧杂卟啉的合成，质谱和光物理性质

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摘要

Free-base octaethylporphyrin (OEP) was converted in two steps (b,b’-dihydroxylation and oxidative diol cleavage with concomitant aldol condensation) to the corresponding oxypyriporphyrin. This conversion was previously described to be applicable only to the NiII complex of OEP. Modified diol cleavage conditions made this reaction sequence now applicable to free-base OEP. The single-crystal structure of the resulting free-base oxypyriporphyrin was determined, proving its near-perfect planarity. The reaction sequence can also be applied to oxypyriporphyrin itself, generating the unACHTUNGTRENUNGprec-ACHTUNGTRENUNGeACHTUNGTRENUNGdented bacteriochlorin-type bis-ACHTUNGTRENUNG(oxypyri)porphyrin as two separable isomers. The ground-state (UV/Vis and fluorescence spectroscopies) and excited- state (transient triplet–triplet absorption, triplet lifetimes, and triplet EPR spectroscopy) photophysical properties of all chromophores are compared with those of OEP, chlorins, and oxochlorins. The pyridone-modified porphyrins possess unique spectroscopic signatures that distinguish them from regular porphyrins or chlorins. The presence of the pyridone moiety alters the ESI+ collision-induced fragmentation properties of these oxypyriporphyrins only to a minor degree when compared with those of OEP or chlorins, confirming their stability.
机译：将游离碱的八乙基卟啉（OEP）分两个步骤（b，b′-二羟基化和氧化二醇裂解并伴随醛醇缩合反应）转化为相应的氧卟啉。先前已描述此转换仅适用于OEP的NiII配合物。修饰的二醇裂解条件使该反应序列现在适用于游离碱OEP。测定了所得的游离碱氧基吡啶卟啉的单晶结构，证明了其近乎完美的平面度。该反应序列还可以应用于氧卟啉本身，产生作为两个可分离的异构体的未ACHTUNGTRENUNGprec-ACHTUNGTRENUNGeACHTUNGTRENUNGdented细菌绿素型双-ACHTUNGTRENUNG（oxypyri）卟啉。将所有生色团的基态（UV / Vis和荧光光谱）和激发态（瞬态三重态-三重态吸收，三重态寿命和三重态EPR光谱）的光物理性质与OEP，二氢卟吩和氧代绿素进行了比较。吡啶酮修饰的卟啉具有独特的光谱特征，可将其与常规卟啉或二氢卟酚区分开。与OEP或二氢卟酚相比，吡啶酮部分的存在仅在较小程度上改变了这些氧吡啶卟啉的ESI +碰撞诱导的断裂特性，从而确认了它们的稳定性。

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