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Synthesis of fluorescent naphthoquinolizines via intramolecular houben-hoesch reaction

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Details

Original languageEnglish
Pages (from-to)553-558
Number of pages6
JournalChemistry - An Asian Journal
Volume10
Issue number3
DOIs
Publication statusPublished - 2015
Publication typeA1 Journal article-refereed

Abstract

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-CH2CN and-CH2CO2Et groups led to compounds bearing a 5-substi-tuted 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 5H-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 eukary-otic cells.

ASJC Scopus subject areas

Keywords

  • Cyclization, Fluorescence, Heterocycles, Pyrenes, Quinolines

Publication forum classification

Field of science, Statistics Finland