ja050760f_si_001.pdf (1.74 MB)

Photorelease of Carboxylic Acids, Amino Acids, and Phosphates from N-Alkylpicolinium Esters Using Photosensitization by High Wavelength Laser Dyes

Download (1.74 MB)
journal contribution
posted on 08.06.2005, 00:00 by Chitra Sundararajan, Daniel E. Falvey
Visible light (>450 nm) is used to efficiently cleave carboxylic acids, amino acids, and phosphates from their N-methyl picolinium esters. Photolysis using pyrromethene dyes PM 546 and PM 597 and also coumarin 6 as photosensitizers effects release of carboxylic acids, N-protected amino acids, and phosphates in quantitative yields. The effective rate of photorelease by the dyes, Φε, was found to be as high as 4500 M-1 cm-1. The photorelease proceeds through photoinduced electron transfer from the dye sensitizers to the N-methyl picolinium group. Fluorescence quenching and laser flash photolysis experiments support the photoinduced electron-transfer mechanism.