Comprehensive exploration of the optical and biological properties of new quinolines based cellular probes
PBN-AR
Instytucja
Instytut Chemii Organicznej Polskiej Akademii Nauk
Informacje podstawowe
Główny język publikacji
en
Czasopismo
DYES AND PIGMENTS (40pkt w roku publikacji)
ISSN
0143-7208
EISSN
Wydawca
ELSEVIER SCI LTD
DOI
URL
Rok publikacji
2017
Numer zeszytu
Strony od-do
119-132
Numer tomu
144
Link do pełnego tekstu
Identyfikator DOI
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Słowa kluczowe
en
Quinoline; Optical properties; Solvatochromism; DFT study; Intracellular probe
Streszczenia
Język
en
Treść
A series of quinoline derivatives containing bithiophene and N-octyl-carbazole moieties and a variety of substituents in the quinoline core were synthesized and characterized. The influence of bithienyl and N-octyl-carbazyl substituents on the photophysical properties of novel quinolines were thoroughly investigated and supported by DFT calculations. The absorption and emission maxima of quinolines are located at 373-412 and 410–606 nm, respectively, which considerably red-shifts when an electron-withdrawing substituent (NO2) is introduced to the quinoline ring. The quantum yield and lifetime for carbazyl-substituted quinolines are considerably higher (Φem = 9–70%, τ = 0.83–5.72 ns) compared to their bithiophene substituted counterparts (Φem = 18–53%, τ = 0.61–1.46 ns) resulting from greater planarity of carbazyl-substituted quinolines as proved by theoretical calculations. The carbazyl functional group in quinolines has immense impact on values of Δμ (13.83–15.50 D) indicating that the electron-donating ability of carbazole moiety relative to bithiophene motif (Δμ = 9.16–13.83) in studied quinolines is more predisposed to intramolecular charge transfer (ICT). The capability of the novel compounds for cellular staining was investigated. All examined quinoline derivatives penetrate cell organelles quickly and efficiently with good overall fluorescence and signal to noise ratio. Relative lack of toxicity make them useful in such applications.
Cechy publikacji
discipline:Chemia
discipline:Chemistry
Original article
Original article presents the results of original research or experiment.
Oryginalny artykuł naukowy
Oryginalny artykuł naukowy przedstawia rezultaty oryginalnych badań naukowych lub eksperymentu.
Inne
System-identifier
PBN-R:819032
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