N-Rich Fused Heterocyclic Systems: Synthesis, Structure, Optical and Electrochemical Characterization

作者：Fusco Sandra; Maglione Cira; Velardo Amalia; Piccialli Vincenzo; Liguori Rosalba; Peluso Andrea; Rubino Alfredo; Centore Roberto

来源：European Journal of Organic Chemistry, 2016, 2016(9): 1772-1780.

DOI：10.1002/ejoc.201501283

• Fused-ring systems
• Nitrogen heterocycles
• Crystal engineering
• Cyclic voltammetry

A new class of N-rich fused heterocyclic compounds containing the triazolo-triazine moiety was synthesized and studied by cyclic voltammetry, UV/Vis spectroscopy, X-ray diffraction, and first principle computations. All the compounds show reversible or quasi-reversible reduction processes, with reduction potentials easily tunable within the class. LUMO energies as low as -3.95 eV have been measured. The UV/Vis spectra show highly structured absorptions, indicative of rigid molecular skeletons. The solid-state packing is dominated by p-p stacking interactions, which are promoted by weak CAr-H center dot center dot center dot N interactions, whereas face-to-edge contacts (T contacts), typical of many fused hydrocarbons, are largely absent.

• 出版日期2016-3