Synthesis, Electrochemistry, Crystal Structures, and Optical Properties of Quinoline Derivatives with a 2,2′-Bithiophene Motif
PBN-AR
Instytucja
Wydział Matematyki, Fizyki i Chemii (Uniwersytet Śląski w Katowicach)
Informacje podstawowe
Główny język publikacji
EN
Czasopismo
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
ISSN
1434-193X
EISSN
Wydawca
URL
Rok publikacji
2014
Numer zeszytu
24
Strony od-do
5256-5264
Numer tomu
2014
Identyfikator DOI
Liczba arkuszy
0,4
Słowa kluczowe
EN
Density functional calculations
Donor-acceptor systems
Electrochemistry
Fluorescence
Luminescence
Streszczenia
Język
EN
Treść
New quinolines bearing a 2,2′-bithiophene motif have been prepared through Ru- and In-catalyzed reactions as well as by Suzuki cross-coupling reactions. The novel quinolines have been characterized by using EI-HRMS and NMR spectroscopy. Additionally, the molecular structures of the novel quinolines were confirmed by X-ray crystallography. The photophysical and electrochemical properties of all quinoline derivatives were investigated by using absorption and luminescence spectroscopy and cyclic voltammetry. The main intense absorption bands associated with the quinoline derivatives were located between 350 and 450 nm. Intense blue-green and orange-red fluorescence, moderate Stokes shifts, and microsecond lifetimes were observed. Quinolines containing one bithiophene moiety underwent oxidation leading to dimerization, whereas bis(bithiophenyl)-substituted quinoline underwent polymerization. All the studied quinolines showed multistep reversible reduction, with 6-nitro-4-phenylquinoline being the easiest to reduce. The study of novel quinoline derivatives indicates a strong correlation between their electrochemical and spectroscopic properties and the character of the substituent (electron-donating or electron-withdrawing) in the quinoline ring.
Inne
System-identifier
0192500104942
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