853377-11-4Relevant academic research and scientific papers
Self-assembly of pyrene boronic acid-based chemodosimeters for highly efficient mercury(II) ion detection
Lee, Sun Woo,Lee, Seung Yeob,Lee, Seoung Ho
, (2019)
A new chemodosimeter consisting of pyrene and boronic acid (1) for the detection of Hg2+ ions is described. The amphiphilic nature of 1 leads to self-assembly in aqueous solution and the high electron density throughout the aggregated pyrene units provides an outstanding platform for energy and electron transport. Self-assembled 1 exhibits a selective and sensitive fluorescence response to Hg2+ ions, where the Hg2+ ion allows a fast transmetallation of 1, which drastically reduces its fluorescence. The Stern-Volmer (SV) quenching constant for the fluorescence quenching of self-assembled 1 by Hg2+ ions is approximately 1.8 × 106 M?1, and Hg2+ ions can be sensed with a detection limit of 6.6 × 10?9 M. In addition, self-assembled 1 exhibits excellent sensing performance at nano-molar concentration levels for Hg2+ ion contamination of tap water, fresh water, and seawater.
Pyrene-based aggregation-induced emission luminogens (AIEgens) with less colour migration for anti-counterfeiting applications
Wang, Xiaohui,Wang, Lirong,Mao, Xiaoyu,Wang, Qingsong,Mu, Zhongfei,An, Li,Zhang, Wan,Feng, Xing,Redshaw, Carl,Cao, Changyong,Qin, Anjun,Tang, Ben Zhong
supporting information, p. 12828 - 12838 (2021/10/06)
Traditional luminescent materials are subject to aggregation-caused quenching, which limits their use for high-technological applications in the solid state. In an attempt to address such issues when using luminescent materials in fluorescent inks, by taking advantage of the aggregation-induced emission (AIE) behaviour, this article presents a set of pyrene-based AIEgens which possess high thermal stability, excellent fluorescence properties, and good biocompatibility. These AIEgens can be utilized as fluorescent inks for anti-counterfeiting applications at ultralow/low concentration (0.004-0.5 wt%) (weightAIEgens?:?weightbinder= 5?:?125?000-5?:?1000) with slight colour migration (27 nm) for different printing substrates. The use of such a fluorescent ink containing pyrene-based AIEgens has extended the scope of application over the range from ultralow to high concentration thereby avoiding the aggregation-caused quenching (ACQ) effect. Additionally, this system would lower the product cost, and be beneficial for the environment. The high-quality fluorescence pattern was found to exhibit good printability on different types of paper by old printing technology (screen printing technology). This work highlights that pyrene-based AIEgens are excellent candidates for use in anti-counterfeiting, and these results have the potential to enrich the practical applications of AIEgens in both academic and industrial fields.
Pyrene-based compound and organic light emitting diode comprising the same
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Paragraph 0299-0305, (2020/05/19)
A pyrene-based compound, and an organic light-emitting diode including the pyrene-based compound are provided.
O-Annulation to Polycyclic Aromatic Hydrocarbons: A Tale of Optoelectronic Properties from Five- To Seven-Membered Rings
Dordevi?, Luka,Milano, Domenico,Demitri, Nicola,Bonifazi, Davide
supporting information, p. 4283 - 4288 (2020/06/24)
We take advantage of the Pummerer oxidative annulation reaction to extend PAHs through the formation of an intramolecular C-O bond with a suitable phenol substituent. Depending on the peripheral topology of the PAH precursor (e.g., pyrene, boron-dipyrromethene, or perylene diimide) five-, six-, and seven-membered O-containing rings could be obtained. The effect of the O-annulations on the optoelectronic properties were studied by various methods with the pyrano-annulated pyrene and BODIPY derivatives depicting quantitative emission quantum yields.
Comparison Study of the Site-Effect on Regioisomeric Pyridyl-Pyrene Conjugates: Synthesis, Structures, and Photophysical Properties
Lu, Qing,Kole, Goutam Kumar,Friedrich, Alexandra,Müller-Buschbaum, Klaus,Liu, Zhiqiang,Yu, Xiaoqiang,Marder, Todd B.
, p. 4256 - 4266 (2020/03/23)
To investigate the "site effect" of pyridyl substituents on a pyrene core, four regioisomeric monopyridyl-pyrene (1-4) and five regioisomeric dipyridyl-pyrene (5-9) conjugates were synthesized and characterized and their structures confirmed by single-crystal X-ray diffraction. The photophysical properties and related frontier orbital features of these compounds have been studied both experimentally and theoretically and demonstrate the dependence of the properties of the compounds on the position of substitution of the pyridyl moieties connecting to the pyrene core. It was found that the absorption spectra of 2- A nd 4-substituted pyrene derivatives display similar and weak influence on the S2 a? S0 excitations, whereas they are quite different from those of 1-substituted isomers. The emission spectra of 1- A nd 4-substituted pyrenes are quite similar, whereas those of 2-substituted isomers display the largest bathochromic shift. The 1,6-disubstituted compound 5 exhibits a near-unity emission quantum yield in solution, which is nearly three times higher than those of other regioisomeric dipyridyl-pyrenes. In addition, the tetrasubstituted 1,6-dipyridyl-3,8-di-n-butyl-pyrene (10) exhibits the highest solid-state quantum yield of 0.24 among all of the 10 pyridyl-pyrenes prepared in this study.
Multiple Electrophilic C-H Borylation of Arenes Using Boron Triiodide
Oda, Susumu,Ueura, Kenta,Kawakami, Bungo,Hatakeyama, Takuji
supporting information, p. 700 - 704 (2020/02/04)
Electrophilic C-H borylation of arenes using boron triiodide has been developed. This reaction proceeded smoothly in the absence of additives, and the diiodoboryl group was installed at the most sterically accessible carbon, where the HOMO is localized to a certain extent. Moreover, regioselective multiple borylation of polycyclic aromatic compounds was achieved by using excess boron triiodide. The borylated intermediates were transformed into a variety of arylboron compounds such as arylboronates, boronic acids, and trifluoroborates.
meta-Nitration of Arenes Bearing ortho/para Directing Group(s) Using C?H Borylation
Li, Xuejing,Deng, Xingwang,Coyne, Anthony G.,Srinivasan, Rajavel
supporting information, p. 8018 - 8023 (2019/05/29)
Herein, we report the meta-nitration of arenes bearing ortho/para directing group(s) using the iridium-catalyzed C?H borylation reaction followed by a newly developed copper(II)-catalyzed transformation of the crude aryl pinacol boronate esters into the corresponding nitroarenes in a one-pot fashion. This protocol allows the synthesis of meta-nitrated arenes that are tedious to prepare or require multistep synthesis using the existing methods. The reaction tolerates a wide array of ortho/para-directing groups, such as ?F, ?Cl, ?Br, ?CH3, ?Et, ?iPr ?OCH3, and ?OCF3. It also provides regioselective access to the nitro derivatives of π-electron-deficient heterocycles, such as pyridine and quinoline derivatives. The application of this method is demonstrated in the late-stage modification of complex molecules and also in the gram-scale preparation of an intermediate en route to the FDA-approved drug Nilotinib. Finally, we have shown that the nitro product obtained by this strategy can also be directly converted to the aniline or hindered amine through Baran's amination protocol.
Preparation and characterization of pyrene modified uridine derivatives as potential electron donors in RNA
Frommer, Jennifer,Karg, Beatrice,Weisz, Klaus,Müller, Sabine
, p. 7663 - 7673 (2018/11/02)
Charge transfer across double stranded DNA was observed for the first time about 20 years ago, and ever since it has been the subject of a large number of studies. RNA has been hardly investigated in this regard, which not least is due to the lack of suitably functionalized ribonucleotide building blocks to serve as electron sources upon incorporation into oligoribonucleotides. We have synthesized two uridine derivatives carrying pyrene or dimethylaminopyrene linked to C5 of the nucleobase. The key to successful synthesis was the adaptation of Suzuki-Miyaura conditions to the coupling of the pyrene moiety with the ribonucleoside. Final decoration of the pyrenylated nucleosides with standard 5′-O- and 2′-O-protecting groups and subsequent 3′-O-phosphitylation delivered the building blocks for incorporation into RNA. Spectroscopic analysis of the two pyrenylated uridines and of the accordingly modified oligonucleotides showed that in particular the dimethyaminopyrene functionalized nucleoside is a promising candidate as an electron source for RNA charge transport studies.
2-Positional pyrene end-capped oligothiophenes for high performance organic field effect transistors
Oniwa, Kazuaki,Kikuchi, Hiromasa,Shimotani, Hidekazu,Ikeda, Susumu,Asao, Naoki,Yamamoto, Yoshinori,Tanigaki, Katsumi,Jin, Tienan
supporting information, p. 4800 - 4803 (2016/04/09)
Three new 2-positional pyrene end-capped oligothiophene co-oligomers, BPynT (n = 1, 2, 3), have been synthesized for application in organic field effect transistors (OFETs). BPy2T showed the highest hole mobility of 3.3 cm2 V-1 s-1 in a single crystal OFET and a good photoluminescence efficiency of 32% in the crystalline state. A green light emission was observed for the OFET based on a BPy2T single crystal.
Amino carbazole bridged molecular forceps and its preparation method and application (by machine translation)
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Paragraph 0044-0047, (2017/03/08)
The invention relates to amine-containing diphenylenimine bridged molecular forceps and its preparation method, it has the following formula by the chemical structural formula of that: is wherein Ar fused ring pyrenyl ; n=1-15 ; R 1, R 2 to the carbon number is 1-6 the alkyl chain of the, its preparation method includes the following steps: 1) in order to 3,6-dibromo diphenylenimine as the reaction raw material, under the alkaline condition, with the excess of the amino compound through reaction, to obtain the different amino carbazole b bromine ; 2) to amino carbazole two bromines as raw materials, by palladium-catalyzed coupling reaction into rigid fused ring Pyren unit, to obtain the different target product. The invention has the following advantages and beneficial effects: 1) it is simple to synthesize, low cost, good separation effect, help to large-scale purification of carbon nano-tube. 2) has good alcohol-soluble, can in ethanol, propanol, and the like in the environment-friendly solvent medium separation of carbon nanotubes, has the advantages of environmental protection, the strong characteristic of practicability. (by machine translation)
