ORGN 402 |
| The near-infrared spectral region has been underutilized for diverse applications owing to the lack of chromophores that afford stability, solubility, synthetic malleability, and tunable photophysical features. Analogues of naturally occurring bacteriochlorophylls are attractive candidates but prior synthetic limitations have restricted their use. To overcome such limitations, a free base dibromobacteriochlorin was prepared by rational synthesis that bears (1) a geminal dimethyl group in each reduced ring to block adventitious dehydrogenation, and (2) bromo groups at the 3- and 13-positions for further chemical modifications. Application of five types of Pd-coupling reactions gave bacteriochlorins bearing 3,13-substituents (H, acetyl, formyl, phenyl, phenylethynyl, or vinyl). This set of bacteriochlorins exhibits an absorption maximum between 713 and 771 nm and fluorescence quantum yield of 0.14 to 0.075. The ability to introduce diverse functional groups and the tunable spectral properties enable synthetic bacteriochlorins to be applied for a wide variety of photochemical applications.
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Heterocycles and Aromatics, Molecular Recognition and Self Assembly
8:00 PM-10:00 PM, Tuesday, April 8, 2008 Morial Convention Center -- Hall A, Poster
Sci-Mix
Division of Organic Chemistry |
