TY - JOUR

T1 - A novel [1,2,4]triazolo[1,5-a]pteridine framework: Synthesis, photophysical properties and material studies

AU - Gazizov, Denis A.

AU - Steparuk, Alexander S.

AU - Demina, N.

AU - Zhilina, Ekaterina F.

AU - Eltsov, Oleg S.

AU - Lebedkin, German S.

AU - Rusinov, Gennady L.

AU - Alexandrov, Alexei E.

AU - Tameev, Alexey R.

N1 - The synthesis and analytical study of organic materials was performed with the financial support of the Russian Science Foundation (Project no. 19-13-00234). D.A.G. A.S.S. and N.S.D is grateful to the partial financial support from the Ministry of Education and Science of the Russian Federation within the framework of the State Assignment for Research (Project No. AAAA-A19-119012490006-1). A.E.A. and A.R.T. are grateful for the support from the Frumkin Institute under the Federal contract No.122011300052–1. Analytical studies were carried out using equipment of the Center for Joint Use “Spectroscopy and Analysis of Organic Compounds” at the Postovsky Institute of Organic Synthesis of the Russian Academy of Sciences (Ural Branch). D.A.G., A.S.S., and N.S.D is grateful to the partial financial support from the Ministry of Education and Science of the Russian Federation within the framework of the State Assignment for Research (Project No. AAAA-A19-119012490006-1). A.E.A. and A.R.T. are grateful for the support from the Frumkin Institute under the Federal contract No.122011300052–1.

PY - 2023

Y1 - 2023

N2 - 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 calculations 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.

AB - 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 calculations 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.

UR - http://www.scopus.com/inward/record.url?partnerID=8YFLogxK&scp=85164226375

U2 - 10.1016/j.dyepig.2023.111507

DO - 10.1016/j.dyepig.2023.111507

M3 - Article

JO - Dyes and Pigments

JF - Dyes and Pigments

SN - 0143-7208

IS - 218

M1 - 111507

ER -