Series of glassy 6-(tert-butyl)-4H-pyran-4-ylidene malononitrile (DCM) derivatives with covalently attached amorphous state promoting bulky triphenyl moieties through several chemical design approaches have been synthesized and investigated for suitability in organic solid state laser applications. Results showed that the bonding type of such functional groups had a considerable influence on glass structure forming dye thermal properties and a little influence on their optical properties. Thermal stability up to 346 oC was achieved with glass transitions in the range from 39 to 138 oC. Incorporation of bulky triphenyl substituents via ester groups showed remarkable amplified spontaneous emission threshold energy value reduction by 1.7 times in comparison to other bonding approaches with excitation threshold energy density up to 91 µJ/cm2. Synthesized dyes show potential as the light-amplification medium component in organic solid state lasers.