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N‐Rich Fused Heterocyclic Systems: Synthesis, Structure, Optical and Electrochemical Characterization
Author(s) -
Fusco Sandra,
Maglione Cira,
Velardo Amalia,
Piccialli Vincenzo,
Liguori Rosalba,
Peluso Andrea,
Rubino Alfredo,
Centore Roberto
Publication year - 2016
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201501283
Subject(s) - chemistry , moiety , cyclic voltammetry , stacking , homo/lumo , electrochemistry , crystallography , triazine , ultraviolet visible spectroscopy , spectroscopy , diffraction , characterization (materials science) , photochemistry , stereochemistry , molecule , organic chemistry , nanotechnology , electrode , materials science , physics , quantum mechanics , optics
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 π–π stacking interactions, which are promoted by weak C Ar –H ··· N interactions, whereas face‐to‐edge contacts (T contacts), typical of many fused hydrocarbons, are largely absent.