Synthesis of fluorescent naphthoquinolizines via intramolecular houben-hoesch reaction
Research output: Contribution to journal › Article › Scientific › peer-review
|Number of pages||6|
|Journal||Chemistry - An Asian Journal|
|Publication status||Published - 2015|
|Publication type||A1 Journal article-refereed|
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.