6217-22-7Relevant academic research and scientific papers
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.
Preparation and luminescence properties of isoquinoline-nucleated polycyclic aromatics
Li, Yanmei,Li, Xinyu,Yu, Tianzhi,Su, Wenming,Wang, Youjia,Zhao, Yuling,Zhang, Hui
, (2020)
Two isoquinoline-nucleated polycyclic aromatic compounds, 4,5-diphenyl-7H-dibenzo[de,g]quinolin-7-one (A) and 3,4-diphenyl-6H-phenanthro[3,4,5-defg]quinolin-6-one (B), were synthesized in high yields through three-component reaction of phenanthrene diketone or pyrene diketone, ammonium acetate and 1,2-diphenylethyne in one-pot. Their structures, thermal stabilities, photophysical properties and energy levels are investigated systematically. Both compounds emit very weak fluorescence in acetone, but their luminescence intensity increased significantly when the water content reaches 50% for A and 40% for B, exhibiting aggregation-induced emission (AIE) characteristics, and showing that the AIE effect of the compound A is stronger than that of the compound B. The vacuum-processed doped devices based on the compound B showed green emission with a maximum brightness of 2162 cd/m2, a maximum current efficiency of 2.97 cd/A and a maximum external quantum efficiency (EQE) of 2.23%.
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
Synthesis of Pyrene-4,5-dione on a 15 g Scale
Walsh, Joshua C.,Williams, Kerry-Lynn M.,Lungerich, Dominik,Bodwell, Graham J.
, p. 5933 - 5936 (2016)
A scalable and efficient method for the synthesis of pyrene-4,5-dione has been developed. The addition of N-methylimidazole (NMI, 5 mol-%) to a known oxidation reaction was shown to marginally improve the yield and dramatically improve the ease of the workup and thus the amount of product isolable in a day by using regular laboratory equipment.
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.
Highly efficient deep-blue organic light-emitting diodes based on pyreno[4,5-d] imidazole-anthracene structural isomers
Liu, Hui,Kang, Liangliang,Li, Jinyu,Liu, Futong,He, Xin,Ren, Shenghong,Tang, Xiangyang,Lv, Changli,Lu, Ping
, p. 10273 - 10280 (2019)
High-efficiency deep-blue luminophores, especially those satisfying the National Television Standards Committee (NTSC) blue standard Commission Internationale de l'éclairage (CIE) coordinates of (0.14, 0.08), are vital for full-color displays and solid-state illumination. However, deep-blue luminescent materials with efficient photoluminescence quantum yields (φPLs) and high external quantum efficiencies (EQEs) over 5% remain very limited. Imidazole has shown great potential in optoelectronic fields owing to its ambipolar nature. Combining imidazole with rigid aromatic rings, such as naphthalene, phenanthrene and pyrene, could effectively enlarge the π-electronic delocalization, reduce non-radiative transitions of molecules and ensure high φPLs in the solid-state. Herein, two symmetrically twisted pyreno[4,5-d]imidazole-anthracene structural isomers, 9,10-bis(4-(10-phenyl-9H-pyreno[4,5-d]imidazol-9-yl)phenyl)anthracene (N-BPyIA) and 9,10-bis(4-(9-phenyl-9H-pyreno[4,5-d]imidazol-10-yl)phenyl)anthracene (C-BPyIA), have been designed and synthesized by connecting one anthracene group with two pyreno[4,5-d]imidazole groups at the N1 and the C2 position, respectively. They both show high φPLs in neat films (46% for N-BPyIA and 54% for C-BPyIA), good thermal stabilities (Td > 541 °C), and appropriate energy levels for carrier injection. N-BPyIA shows better performance than C-BPyIA when applied in OLEDs. The non-doped device based on N-BPyIA shows sky blue emission with CIE coordinates of (0.22, 0.31), achieving a high EQE of 5.63% with a low efficiency roll-off. In particular, a doped device with better performance is further realized, providing an EQE of 7.67% and deep-blue emission (CIE (0.15, 0.10)), which is very close to the NTSC standard. Such high OLED efficiency may be ascribed to triplet energy harvesting by triplet-triplet annihilation. And to our best knowledge, this is one of the best outcomes of deep-blue imidazole-based fluorescent OLEDs. The results also pave the way for a new type of high-efficiency deep-blue organic luminescent materials regulated by structural isomerization.
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.
A Three-Step Synthesis of 4H-Cyclopenta[def]phenanthrene from Pyrene
Filippov, Dmitri V.,Overkleeft, Hermen S.,Schneider, Grégory F.,van der Ham, Alex
supporting information, p. 2013 - 2017 (2021/06/25)
4H-Cyclopenta[def]phenanthrene (CPP) is a valuable building block in the production of photoactive polymers, which find use in a wide range of organic electronic applications. Of particular importance is their use in the development of blue-colored, organic light-emitting diodes (OLEDs), which remains a challenge in the field. Unfortunately, commercial sources and synthetic procedures known in the literature are unable to provide enough CPP for large scale implementation. Herein, we report on the development of a novel, gram-scale synthesis of CPP in three steps, starting from pyrene. The key steps in our methodology are the ring contraction of pyrene-4,5-dione to oxoCPP in a single step, as well as the direct reduction of oxoCPP to CPP. Apart from the small number of synthetic steps, our methodology benefits from the use of relatively non-hazardous reagents, together with optimized purification procedures, making CPP accessible in useful quantities.
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.
Pyrenedione-Catalyzed α-Olefination of Nitriles under Visible-Light Photoredox Conditions
Bains, Amreen K.,Ankit, Yadav,Adhikari, Debashis
supporting information, p. 2019 - 2023 (2021/04/05)
Herein, we report a combination of pyrenedione (PD) and KOtBu to achieve facile alcohol dehydrogenation under visible-light excitation, where aerobic oxygen is utilized as the terminal oxidant. The resulting carbonyl compound can be easily converted to vinyl nitriles in a single-pot reaction, at 60 °C in 6-8 h. This environmentally benign, organocatalytic approach has distinct advantages over transition-metal-catalyzed α-olefination of nitriles, which often operate at a significantly higher temperature for an extended reaction time.
