Mild and efficient synthetic procedures were developed for the preparation
of a series of adenine, thymine and uracil-derivatives in high yields. In this respect,
four derivatives were derived by introducing various substituents flanked by two
methylene groups at the 1- and 9- positions of pyrimidine and purine bases, respectively.
The other two were prepared from 6-amino-1,3-dimethyluracil or 5,6-diamino-
1,3-dimethyluracil by diazotization or aldehyde condensation. The photophysical
characterization in a number of organic solvents with diverse polarities and in aqueous
solutions at various pH, have been subjected to multiple regression analysis with more
than ten different solvent parameters. The effects of solvent polarity and hydrogen
bonding on the absorption and emission spectra were interpreted in the light of theoretical
predictions. The validity of the regression models has been established from
the linearity of the calculated and observed transition energy relating to absorption spectra and Stokes
shift. This deep investigation provides realistic depiction of solvent effects on absorption and emission
spectral properties of nucleobase derivatives.
Keywords: Nucleobase derivatives, esters, hydrazides, schiff bases, azodyes, benzimidazoles, solvent polarity, absorption/
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