Institute of Chemistry, Faculty of Mathematics, Physics and Chemistry, University of Silesia, Szkolna 9, 40-007, Katowice, Poland.
Institute of Physics, University of Silesia, 75 Pulku Piechoty 1, 41-500, Chorzow, Poland.
Chemistry. 2018 Jul 5;24(38):9622-9631. doi: 10.1002/chem.201801123. Epub 2018 Jun 6.
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.
六种新型荧蒽衍生物，即三个末端取代的和三个双（荧蒽）单元，分别带有芴、联噻吩和咔唑间隔基，通过[2+2+2]环加成反应得到并完全表征。基于所进行的研究，得到的衍生物可分为给体-受体（D-A）和受体-给体-受体（A-D-A）体系，其中荧蒽单元作为吸电子单元。光学结果表明，新型荧蒽衍生物在λ=236-417nm 范围内吸收光，这源于共轭体系内的π→π 跃迁。化合物表现出从深蓝色到绿色的荧光，这主要源于分子内电荷转移（ICT）态。在溶液（ϕ=0.22-0.57）和固态（ϕ=0.18-0.44）中，荧蒽衍生物观察到高斯托克位移和高量子产率。所有衍生物在低电位下均显示多步氧化过程。所提出的化合物的电子结构还得到了时间依赖的密度泛函理论计算的支持。
