Synthesis of Three Asymmetric N-Confused Tetraarylporphyrins

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• 作者：Rajendra Acharya ; Liladhar Paudel ; Jojo Joseph ; Claire E. McCarthy ; Venkat R. Dudipala ; Jody M. Modarelli ; David A. Modarelli
• 刊名：The Journal of Organic Chemistry
• 出版年：2012
• 出版时间：July 20, 2012
• 年：2012
• 卷：77
• 期：14
• 页码：6043-6050
• 全文大小：402K
• 年卷期：v.77,no.14(July 20, 2012)
• ISSN：1520-6904

文摘

Two monosubstituted and one tetrasubstituted N-confused porphyrins (1鈥?b>3) were prepared in ca. 3鈥?% yields using a [2 + 2] synthesis. The monosubstituted porphyrins have carbomethoxy (1) or nitro (2) substituents on one of the meso-phenyl groups, while the meso-phenyl groups of the third NCP (3) are substituted with nitro, bromo, and methyl groups in an AB₂C pattern. The specific regiochemistry of the aryl rings around the macrocycle in each porphyrin was definitively determined using a combination of 1D (¹H and ¹³C) and 2D (gHMBC, gHSQC and ROESY) NMR spectroscopy. The absorption spectra of 1鈥?b>3 in CH₂Cl₂ are similar to those of N-confused tetraphenylporphyrin (NCTPP) but have Soret and Q bands that are shifted to lower energies with smaller extinction coefficients in comparison to those for NCTPP.