STUDIES OF THE ANTENNA EFFECT IN POLYMER-MOLECULES .24. SOLAR PHOTOSYNTHESIS OF PREVITAMIN-D3 IN AQUEOUS-SOLUTIONS OF POLY(SODIUM STYRENE-SULFONATE-CO-2-VINYLNAPHTHALENE)
M. Nowakowska et al., STUDIES OF THE ANTENNA EFFECT IN POLYMER-MOLECULES .24. SOLAR PHOTOSYNTHESIS OF PREVITAMIN-D3 IN AQUEOUS-SOLUTIONS OF POLY(SODIUM STYRENE-SULFONATE-CO-2-VINYLNAPHTHALENE), Journal of the American Chemical Society, 115(14), 1993, pp. 5975-5981
The photochemical step in the synthesis of vitamin D3 in an aqueous so
lution of poly(sodium styrenesulfonate-co-2-vinylnaphthalene) (PSSS-VN
) was studied using solar light. The photoisomerization of 7-dehydroch
olesterol to previtamin D3 was found to be exceptionally clean and eff
icient. The process was shown to be photosensitized by the pendant nap
hthalene chromophores in the copolymer via singlet-singlet energy tran
sfer. The lack of tachysterol, a major side product formed during phot
oisomerization in organic solution, was explained by triplet-sensitize
d isomerization of tachysterol to previtamin. Triplet-triplet energy t
ransfer from excited polymeric naphthalene chromophores to tachysterol
is efficient because of the high local concentration of tachysterol i
n the vicinity of the energy donors.