Journal of the American Chemical Society, Vol.131, No.3, 931-931, 2009
Nucleobase Mediated, Photocatalytic Vesicle Formation from an Ester Precursor
We report the use of photoinduced electron transfer to drive reductive cleavage of an ester to produce bilayer-forming molecules; specifically, visible photolysis in a mixture of a decanoic acid ester precursor, hydrogen donor molecules, and a ruthenium-based photocatalyst that employs a linked nucteobase (8-oxo-guanine) as an electron donor generates decanoic acid. The overall transformation of the ester precursor to yield vesicles represents the use of an external energy source to convert nonstructure forming molecules into amphiphites that spontaneously assemble into vesicles. The core of our chemical reaction system uses an 8-oxo-G-Ru photocatalyst, a derivative of [tris(2,2'bipyridine)-Ru(II)](2+).