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Permethylated Salts and Radicals Derived from Azo peri‐ Naphthalenes
Author(s) -
Bohle D. Scott,
Chua Zhijie,
Johnstone Timothy,
Moiseev Andrey G.,
Perepichka Inna,
Rosadiuk Kristopher A.
Publication year - 2012
Publication title -
chempluschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.801
H-Index - 61
ISSN - 2192-6506
DOI - 10.1002/cplu.201200021
Subject(s) - chemistry , raman spectroscopy , triazene , radical , benzophenone , density functional theory , electron paramagnetic resonance , trifluoromethanesulfonate , azine , photochemistry , triazine , cyclic voltammetry , triphenylene , computational chemistry , medicinal chemistry , molecule , polymer chemistry , organic chemistry , electrochemistry , physics , nuclear magnetic resonance , electrode , optics , catalysis
By careful choice of reaction conditions 1‐methylnaphtho[1,8‐ de ]‐1,2,3‐triazine and 1,3‐dimethylnaphtho[1,8‐ de ]‐1,2,3‐triazinium triflate are readily prepared by the alkylation of 1 H ‐naphtho[1,8‐ de ]‐1,2,3‐triazine. The electronic spectra for these bathochromically shifted dyes are reported for a range of solvents as are their vibrational spectra and theoretical structures from density functional theory, B3LYP/6‐311++G**. The 15 N substitution into the middle nitrogen atom allows for the identification of strong azine bands in the IR and Raman spectra as well as in the 15 N NMR spectrum. X‐ray crystallography is used to characterize the solid‐state structures of two of these new triazine derivatives and these structures are used to benchmark the theoretical and spectroscopic discussions. The corresponding 1,3‐dimethyltriazinium radical is prepared and characterized by cyclic voltammetry, spectroelectrochemistry, and EPR spectroscopy. Unlike the related transient 1,2,4‐triazene radicals, the 1,3‐dimethyl‐1,2,3‐naphthotriazyl radical is markedly more stable.