Template Synthesis Of Two Porphyrin Cages And A Cyclic Porphyrin Nanoring

Porphyrins and metalloporphyrins is a kind of very important compounds which exist widely in nature, such as in chlorophyll, heme and cytochrome P450. Metalloporphyrins can be assembled by templates such as nitrogen-containing heterocyclic compounds, which lead to some unique chemical and photophysical properties. This thesis aimed on the design and synthesis of some new multi-porphyrin cages and cyclic compounds with template-directed methods and achieved the results as follows:(1) With1,4-diazabicyclo[2.2.2]octane (DABCO) as the template, two alkene-derived metalloporphyrin molecules formed a sandwich-type self-assembly, from which2similar bisporphyrin cages were synthesized by one-pot olefin metathesis reaction with the yields up to60%. These cages were characterized by1H NMR,’H-’H COSY,13C NMR, MALDI-TOF MS, and UV spectra. This preorgnization and template-directed strategy provides a new method for the efficient synthesis of porphyrin cages.(2) With2,4,6-tris(4-pyridyl)-1,3,5-triazine (TPT) as the template, three alkene-derived metalloporphyrin molecules formed a triporphyrin self-assembly, from which a trisporphyrin cyclic compound was synthesized by one-pot olefin metathesis reaction with the yields up to65%. This trisporphyrin cyclic compound was characterized by1H NMR,1H-1H COSY,13C NMR, MALDI-TOF MS, and UV spectra. This work provides a new method for the efficient synthesis of covalent connected multiporphyrin structures.(3) We synthesized an AABB-type porphyrin containing two olefin chains and two tetraethyleneglycol chains, from which a water-soluble bisporphyrin cyclic compounds can be prepared.