6217-22-7Relevant articles and documents
Synthesis, Structures, and Optoelectronic Properties of Pyrene-Fused Thioxanthenes
Zhang, Shiqian,Liu, Zhiqiang,Fang, Qi
, p. 1382 - 1385 (2017)
A series of pyrene-fused thioxanthenes have been synthesized via a new concise route, and their crystal structures and photophysical properties have been fully investigated. The eight-ring fused dipyrene-thioxanthene (DPTA) can crystallize to monoclinic and triclinic X-ray structures, and their precursor has been isolated as two stable atropisomers with different photophysical properties. The EHOMO becomes higher and the Eg become narrower as more thioxanthene unit being fused with pyrene.
Pyrenoimidazole-based deep-blue-emitting materials: Optical, electrochemical, and electroluminescent characteristics
Kumar, Dhirendra,Thomas, K. R. Justin,Lin, Ching-Chiao,Jou, Jwo-Huei
, p. 2111 - 2124 (2013)
A series of pyrenoimidazoles that contained various functional chromophores, such as anthracene, pyrene, triphenylamine, carbazole, and fluorene, were synthesized and characterized by optical, electrochemical, and theoretical studies. The absorption spectra of the dyes are dominated by electronic transitions that arise from the pyrenoimidazole core and the additional chromophore. All of the dyes exhibited blue-light photoluminescence with moderate-to-high quantum efficiencies. They also displayed high thermal stability and their thermal-decomposition temperatures fell within the range 462-512 °C; the highest decomposition temperature was recorded for a carbazole-containing dye. The oxidation propensity of the dyes increased on the introduction of electron-rich chromophores, such as triphenylamine or carbazole. The application of selected dyes that featured additional chromophores such as pyrene, carbazole, and triphenylamine as blue-emissive dopants into multilayered organic light-emitting diodes with a 4,4′-bis(9H-carbazol-9-yl)biphenyl (CBP) host was investigated. Devices that were based on triphenylamine- and carbazole-containing dyes exhibited deep-blue emission (CIE 0.157, 0.054 and 0.163, 0.041), whereas a device that was based on a pyrene-containing dye showed a bright-blue emission (CIE 0.156, 0.135). Deep-blue something: New pyrenoimidazoles showed blue emission with a high quantum efficiency and thermal stability and low oxidation potential. The 10-pyrenyl pyrenoimidazole gave a driving voltage of 5.3 eV and a brightness of 2736 cd m-2. Copyright
Two pyrene-based S-containing atropisomers: Different structures and different Ag+-response behaviors of their monomer-excimer emission
Jin, Ying-ying,Fang, Qi,Zhang, Shi-qian,Liu, Zhi-qiang
, p. 129 - 133 (2019)
Different structures and different Ag+-response behaviors of a pair of pyrene-based S-containing atropisomers, namely s-BSPPy and a-BSPPy, have been investigated. The calculated high rotation barrier indicates that the two atropisomers are non-interconvertible. In polar solvents, s-BSPPy exhibits excimer emission but a-BSPPy does not. Based on the X-ray structures and the DFT calculated intermolecular interactions, the excimer of s-BSPPy is suggested to take a non-parallel edge-to-face λ-shaped geometry. Especially, s-BSPPy exhibits ratiometric excimer-off and monomer-on emission as a unique response to Ag+ in solutions, while no ratiometric Ag+-response was observed for a-BSPPy.
Relationship Between Molecular Structure, Single crystal Packing and Self-Assembly Behavior: A Case Based on Pyrene Imide Derivatives
Chen, Jiawen,Chen, Wangqiao,Han, Hongjing,Li, Xiaojun,Qiu, Meizhen,Zhang, Qichun,Zhang, Shilong
supporting information, (2021/12/08)
Development of new n-type one-dimensional (1D) self-assembly nanostructure and a clear understanding of the relationship between molecular structure and self-assembly behavior are important prerequisites for further designing and optimizing organic optoelectronic nanodevice. In this article, a series of n-type organic semiconductor materials based on pyrene imide were successfully synthesized through [4+2] cycloaddition reactions and their preliminary optical and electrochemical properties were studied. The simulated HOMO-LUMO bandgaps via DFT tallied with the experimental data well. The self-assembly of these materials showed needle or fiber-like morphologies, indicating that different conjugation degree or alkyl group had significant influence on their self-assembly behaviors. Furthermore, the single-crystal packing for these molecules were analyzed and it was found out that the changes of conjugated backbone and functional group would affect certain crystal lattice parameter significantly, such as the intermolecular packing distance and crystal size etc, which would further result in different self-assembly morphology.
Fluorescence Sensors for Bismuth (III) Ion from Pyreno[4,5-d]imidazole Derivatives
Chanawungmuang, Nichapa,Sukwattanasinitt, Mongkol,Rashatasakhon, Paitoon
, p. 301 - 308 (2020/10/06)
Three pyreno[4,5-d]imidazole derivatives are synthesized and evaluated as fluorescent sensors for bismuth (III) ion. The target compounds are prepared in 55–86% yields from a condensation reaction between pyrene-4,5-dione and aromatic aldehydes. The compound bearing a phenolic group can selectively detect bismuth (III) ion via fluorescence enhancement with a detection limit of 1.20?μm in CH3CN-DMSO mixture and 3.40?μm in 10% pH5 aqueous in CH3CN-DMSO mixture. The sensing mechanism involving a formation of coordination complex is investigated by UV-VIS and fluorescence titrations, 1H-NMR and the decomplexation of the bismuth complex by sulfide ion. The application of this sensor for quantitative analysis of spiked bismuth (III) ion in real water samples from two different sources is demonstrated.
Synthesis, Photophysical and Electronic Properties of New Red-to-NIR Emitting Donor–Acceptor Pyrene Derivatives
Merz, Julia,Dietz, Maximilian,Vonhausen, Yvonne,W?ber, Frederik,Friedrich, Alexandra,Sieh, Daniel,Krummenacher, Ivo,Braunschweig, Holger,Moos, Michael,Holzapfel, Marco,Lambert, Christoph,Marder, Todd B.
, p. 438 - 453 (2019/11/26)
We synthesized new pyrene derivatives with strong bis(para-methoxyphenyl)amine donors at the 2,7-positions and n-azaacene acceptors at the K-region of pyrene. The compounds possess a strong intramolecular charge transfer, leading to unusual properties such as emission in the red to NIR region (700 nm), which has not been reported before for monomeric pyrenes. Detailed photophysical studies reveal very long intrinsic lifetimes of >100 ns for the new compounds, which is typical for 2,7-substituted pyrenes but not for K-region substituted pyrenes. The incorporation of strong donors and acceptors leads to very low reduction and oxidation potentials, and spectroelectrochemical studies show that the compounds are on the borderline between localized Robin-Day class-II and delocalized Robin-Day class-III species.
