ACID BASE CHARACTERIZATION OF TRIAZOLO-TRIAZOLE HETEROCYCLIC SYSTEMS

Heterocycles are key compounds of synthetic chemistry. Besides their long standing and relevant application as drugs and bioactive compounds, aromatic heterocycles are playing a fundamental role in modern material chemistry as building blocks of conjugated active molecules in many emerging fields of organic electronics and optoelectronics: conducting polymers, organic field-effect transistors,[1] organic solar cells,[2] nonlinear optically active compounds.[3] In this work we propose a study of acid-base properties of four [1,2,4]triazolo[3,2-c][1,2,4]triazole systems[4]. The experimental method elected consists of potentiometric, spectrophotometric titrations, in constant ionic medium NaCl 0.5M at 25.00±0.02°C. Electronic absorption spectra have been interpreted with the following equilibria: These results shown that the acid-base properties of [1,2,4]triazolo[3,2- c][1,2,4]triazole derivatives critically depends on the substituents at the heterobicycle. [1] J. Zaumseil, H. Sirringhaus, Chem. Rev., 2007, 107, 1296-1323; b) Y. Wen, Y. Liu, Adv. Mater., 2010, 22,1-15. [2] J. Li, A. C. Grimsdale, Chem. Soc. Rev. 2010, 39, 2399-2410. [3] S. H. Jang, A. K. Jen, Introduction to Organic Electronic and Optoelectronic Materials and Devices (Eds. S. S. Sun, L. R. Dalton) CRC Press, Boca Raton (FL), 2008. [4] R. Centore, S. Fusco, A. Capobianco, V. Piccialli, S. Zaccaria, and A. Peluso, European Journal of Organic Chemistry, 2013, 18, 3721-372