A comparison of linear optical properties and redox properties in chalcogenopyrylium dyes bearing ortho-substituted aryl substituents and tert-butyl substituents.

Abstract

A series of thiapyrylium pentamethine dyes (4 and 12-15) bearing 2,2'-di-tert-butyl-6,6'-diphenyl, 2,2'-di-tert-butyl-6,6'-bis(2,6-dimethylphenyl), 2,2'-di-tert-butyl-6,6'-bis(2-methylphenyl), 2,2',6,6'-tetrakis(2,6-dimethylphenyl), and 2,2',6,6'-tetrakis(2-methylphenyl) substituents, respectively, were prepared and their linear optical properties and electrochemical redox properties were measured and compared to thiapyrylium pentamethine dyes 3 and 5. The tert-butyl and 2,6-dimethylphenyl substituents give nearly identical chromophores with respect to values of lambda(max), molar extinction coefficients (epsilon), bandwidths at half-height (nu(1/2)), and lack of absorption in the visible spectrum. The 2-methylphenyl substituent imparts linear optical properties that are intermediate between those of the tert-butyl and phenyl substituents. The 2,6-dimethylphenyl and 2-methylphenyl substituents impart greater oxidative stability based on anodic shifts in oxidation potential.

Cite this paper

@article{Panda2003ACO, title={A comparison of linear optical properties and redox properties in chalcogenopyrylium dyes bearing ortho-substituted aryl substituents and tert-butyl substituents.}, author={Jagannath Panda and Peter R Virkler and Michael R Detty}, journal={The Journal of organic chemistry}, year={2003}, volume={68 5}, pages={1804-9} }