Department of Chemistry, University of Cologne, Köln, Germany.
Photochem Photobiol Sci. 2011 Sep;10(9):1431-5. doi: 10.1039/c1pp05052d. Epub 2011 Apr 12.
Carbohydrate-decorated meso-tetraarylporphyrins P-G and P-C were synthesized via Lewis-acid catalyzed condensation of acetylated carbohydrate-substituted benzaldehydes and pyrrole. Their efficiency of singlet oxygen production was compared with the corresponding non-substituted porphyrin. The oxidation of the spin trap molecule TEMP (2,2,6,6-tetramethyl-4-piperidone) by singlet oxygen to TEMPO was measured by ESR spectroscopy, showing higher reaction rates for the sugar porphyrins. These results were corroborate by laser flash photolysis measurements that resulted in higher triplet lifetimes of glucosyl- and cellobiosyl porphyrins in comparison with tetrakis(4-hydroxyphenyl)porphyrin. Low ee was detected in the photooxygenation of ethyl tiglate.
糖基修饰的介孔四芳基卟啉 P-G 和 P-C 通过路易斯酸催化乙酰化糖取代苯甲醛和吡咯的缩合反应合成。它们的单线态氧产生效率与相应的未取代卟啉进行了比较。通过 ESR 光谱测量，单线态氧将自旋捕获分子 TEMP（2,2,6,6-四甲基-4-哌啶酮）氧化为 TEMPO，显示出糖基卟啉具有更高的反应速率。这些结果通过激光闪光光解测量得到了证实，结果表明与四（4-羟基苯基）卟啉相比，葡萄糖基和纤维二糖基卟啉的三重态寿命更高。在乙基惕格酸的光氧化中检测到低对映选择性。
