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Luminescent‐Substituted Fluoranthenes—Synthesis, Structure, Electrochemistry, and Optical Properties
Author(s) -
Slodek Aneta,
Maroń Anna,
Pająk Michał,
Matussek Marek,
GrudzkaFlak Iwona,
Małecki Jan G.,
Świtlicka Anna,
Krompiec Stanisław,
Danikiewicz Witold,
Grela Małgorzata,
Gryca Izabela,
Penkala Mateusz
Publication year - 2018
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201801123
Subject(s) - fluoranthene , intramolecular force , photochemistry , carbazole , acceptor , fluorene , fluorescence , luminescence , chemistry , cycloaddition , conjugated system , electrochemistry , materials science , organic chemistry , optoelectronics , polymer , catalysis , physics , quantum mechanics , anthracene , condensed matter physics , electrode
Six novel fluoranthene derivatives, namely, three terminally substituted and three bis(fluoranthene) units with fluorene, bithiophene, and carbazole spacers, were obtained through [2+2+2] cycloaddition and characterized completely. Based on the conducted studies, the obtained derivatives can be classified as donor–acceptor (D‐A) and acceptor‐donor‐acceptor (A‐D‐A) systems, in which the fluoranthene unit acts as an electron‐withdrawing unit. The optical results revealed that novel fluoranthene derivatives absorb light in the range λ =236–417 nm, which originates from a π→π * transition within the conjugated system. The compounds exhibit fluorescence that range from deep blue to green, which mainly arises from intramolecular charge transfer (ICT) states. High Stoke shifts and high quantum yields in solution ( ϕ =0.22–0.57) and in the solid state ( ϕ =0.18–0.44) have been observed for fluoranthene derivatives. All the derivatives display multistep oxidation processes at low potentials. The electronic structure of the presented compounds is additionally supported by time‐dependent DFT computations.