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Syntheses and spectral properties of 2,3,7,8‐tetracyano‐5,10‐dihydrodipyrazino[2,3‐ b :2′,3′‐ e ]pyrazine
Author(s) -
Jaung JaeYun,
Fukunishi Koushi,
Matsuoka Masaru
Publication year - 1997
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570340251
Subject(s) - chemistry , pyrazine , intramolecular force , intermolecular force , electroluminescence , fluorescence , molecular orbital , photochemistry , fluorescence spectroscopy , crystallography , molecule , stereochemistry , organic chemistry , physics , layer (electronics) , quantum mechanics
Base catalized intermolecular cyclization of 2‐amino‐3‐chloro‐5,6‐dicyanopyrazines gave 5,10‐disubsti‐tuted‐2,3,7,8‐tetracyano‐5,10‐dihydrodipyrazino[2,3‐ b :2′,3′‐c]pyrazines 11–20. These compounds have rather small molecular size but have strong intramolecular charge‐transfer chromophoric system. They have strong fluorescence in solution and some have fluorescence even in the solid state which are very important to evaluate their electroluminescence property as an emitter for electroluminescence devices. The physical, structural, and electronic properties of these new 2,3,7,8‐tetracyano‐5,10‐dihy‐drodipyrazino[2,3‐ b :2′3′‐ e ]pyrazines were studied using uv‐visible spectroscopy and the Pariser‐Parr‐Pople molecular orbital calculation method.