ORGN 172 |
| The effect of sterically bulky mesityl substituents on the stability of meso-substituted phlorin was examined. Three different phlorins bearing zero, two, or three mesityl substituents were prepared via alkylation of the corresponding porphyrins. The stability of the phlorins in dilute solution was examined by monitoring UV-vis and mass spectral changes as a function of time upon exposure to ambient light. Consistent with the literature, phlorin 1a was found to have a short half-life of <15 min. Phlorin 1b was similarly unstable. In contrast, phlorin 1c displayed an improved half-life—exceeding 90 min in some solvents. In addition, UV-vis and mass spectral analysis revealed differences in the degradation products of each phlorin. The results of this study show that the selection of peripheral substituents can have a significant effect on the stability of phlorin.
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Heterocycles, Aromatics, Materials, Devices, Switches, Combinatorial Chemistry, Metal-Mediated Reactions
8:00 PM-10:00 PM, Sunday, 13 March 2005 Convention Center -- Hall D, Poster
Division of Organic Chemistry |
