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Synthesis of Fluorescent Naphthoquinolizines via Intramolecular Houben–Hoesch Reaction
Author(s) -
Stasyuk Anton J.,
Smoleń Sabina,
GlodkowskaMrowka Eliza,
Brutkowski Wojciech,
Cyrański Michał K.,
Tkachenko Nikolai,
Gryko Daniel T.
Publication year - 2015
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201403339
Subject(s) - intramolecular force , moiety , chemistry , fluorescence , absorption (acoustics) , pyrene , solvent , salt (chemistry) , stereochemistry , photochemistry , medicinal chemistry , organic chemistry , materials science , physics , quantum mechanics , composite material
The repertoire of synthetic methods leading to aza‐analogues of polycyclic aromatic heterocycles has been enlarged by the discovery of the rearrangement of 10‐substituted benzo[ h ]quinolines into compounds bearing an azonia‐pyrene moiety. Acid‐mediated intramolecular cyclization of derivatives bearing ‐CH 2 CN and ‐CH 2 CO 2 Et groups led to compounds bearing a 5‐substituted benzo[ de ]pyrido[3,2,1‐ ij ]quinolinium core. Advanced photophysical studies including time‐correlated single photon counting (TCSPC) and transient absorption spectroscopy of 5‐aminobenzo[ de ]pyrido[3,2,1‐ ij ]quinolin‐4‐ium salt and 5 H‐ benzo[ de ]pyrido[3,2,1‐ ij ]quinolin‐5‐one showed their promising optical properties such as high fluorescence quantum yields (37–59 %), which was almost independent of the solvent, and high tenability of the absorption band position upon changing the solvent. The benzo[ de ]pyrido[3,2,1‐ ij ]quinolinium salt selectively stains nucleic acids (in the nucleus and mitochondria) in eukaryotic cells.