期刊
ORGANIC CHEMISTRY FRONTIERS
卷 4, 期 4, 页码 534-544出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/c6qo00771f
关键词
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资金
- FCT (Fundacao para a Ciencia e a Tecnologia, Portugal) [UID/MULTI/04378/2013-POCI/01/0145/FERDER/007728, UID/QUI/50006/2013-POCI/01/0145/FERDER/007265]
- QOPNA research project [FCT UID/QUI/00062/2013]
- national funds [PTDC/QEQ-QOR/6160/2014]
- FEDER under the PT2020 Partnership Agreement
- CINECA under the ISCRA initiative [IsC42]
- National Programme for Scientific Re-equipment [REDE/1517/RMN/2005]
- POCI (FEDER)
- FCT
- [M-ERA-NET/0005/2014]
- Fundação para a Ciência e a Tecnologia [M-ERA-NET/0005/2014] Funding Source: FCT
The 1,3-dipolar cycloaddition reaction of meso-tetraarylporphyrins with nitrones gives isoxazolidine-fused chlorins. Depending on the substitution pattern on the meso-aryl groups and the nitrone, the chlorins can be obtained in high yields (up to 91%). Bacteriochlorin-type bisadducts are also obtained, although in low yield, from the reaction of meso-tetrakis(pentafluorophenyl) porphyrin with N-methyl, N-cyclohexyl or N-benzyl nitrone. The structure of a bis(N-benzyl isoxazolidine-fused) bacteriochlorin was determined by single-crystal X-ray diffraction and rationalized by DFT calculations. To further explore the nature of site selectivity in the formation of bisadducts, isomeric mixed bacteriochlorins and iso-bacteriochlorins were synthesized by two complementary routes that involved the sequential addition of two types of 1,3-dipoles to the porphyrin macrocycle: a nitrone and an azomethine ylide. The photo-physical properties of the mixed bacteriochlorins were evaluated and the results were compared with the reported data for other meso-tetraarylbacteriochlorins.
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