A novel [1,2,4]triazolo[1,5-a]pteridine framework: Synthesis, photophysical properties and material studies

The synthesis of novel [1,2,4]triazolo[1,5-a]pteridine (TPt) derivatives was carried out starting from [1,2,4] triazolo[1,5-a]pyrimidine-6,7-diamines and 1,2-dicarbonyl compounds. For obtained TPt DFT/TD-DFT calcu-lations were performed with subsequent complex photophysical and electrochemical studies. The substituent in the pyrazine ring of TPt framework proved to have a higher effect on photophysical properties than that in the triazole ring. The fluorescence quantum yields of studied compounds were generally low (3-23%). However, it was shown that some of TPt was sensitive to trace amounts of organic peroxides (about 100 ppm), which will make it possible to create test systems based on them. On the other hand, low-lying HOMO energy levels and the energy gap values of TPt (2.63 eV < E0-0 < 2.97 eV) as well as the electron mobility in solid-state films measured by the conventional CELIV technique (approximately 10-4 cm2 V-1 s- 1) make these materials promising for the further use in organic electronic devices.

Automated summary

Novel [1,2,4]triazolo[1,5-a]pteridine derivatives were synthesized for the creation of test systems based on them. It was found that the substituent in the pyrazine ring of the TPt framework had a stronger influence on photophysical properties than that in the triazole ring. Although the fluorescence quantum yields of the compounds were generally low (3-23%), some of the TPt derivatives showed sensitivity to trace amounts of organic peroxides, making them promising for test systems. Additionally, the low-lying HOMO energy levels, energy gap values, and electron mobility of TPt materials suggest their potential use in organic electronic devices.