- Stepwise Adsorption of Alkoxy-Pyrene Derivatives onto a Lamellar, Non-Porous Naphthalenediimide-Template on HOPG
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The development of new strategies for the preparation of multicomponent supramolecular assemblies is a major challenge on the road to complex functional molecular systems. Here we present the use of a non-porous self-assembled monolayer from uC33-NDI-uC33, a naphthalenediimide symmetrically functionalized with unsaturated 33 carbon-atom-chains, to prepare bicomponent supramolecular surface systems with a series of alkoxy-pyrene (PyrOR) derivatives at the liquid/HOPG interface. While previous attempts at directly depositing many of these PyrOR units at the liquid/HOPG interface failed, the multicomponent approach through the uC33-NDI-uC33 template enabled control over molecular interactions and facilitated adsorption. The PyrOR deposition restructured the initial uC33-NDI-uC33 monolayer, causing an expansion in two dimensions to accommodate the guests. As far as we know, this represents the first example of a non-porous or non-metal complex-bearing monolayer that allows the stepwise formation of multicomponent supramolecular architectures on surfaces.
- Heideman, G. Henrieke,Berrocal, José Augusto,St?hr, Meike,Meijer,Feringa, Ben L.
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- A novel supermolecular tetrameric vanadate-selective colorimetric and "off-On" sensor with pyrene ligand
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Tris(2-((ethylimino)methyl)pyren-1-ol)amine (1) was synthesized and introduced as the first tetrameric vanadate fluorescence sensor, the entire binding of which was successfully accomplished in two steps with distinct colorimetric changes and "off-on" fluorescent enhancement.
- Zhou, Ying,Jung, Ji Young,Jeon, Hye Ryeong,Kim, Youngmee,Kim, Sung-Jin,Yoon, Juyoung
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- Biotransformation of Pyrene by Cell Cultures of Soybean (Glycine max L.), Wheat (Triticum aestivum L.), Jimsonweed (Datura stramonium L.), and Purple Foxglove (Digitalis purpurea L.)
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The metabolism of the four-ringed polycyclic aromatic hydrocarbon (PAH) pyrene was investigated using cell suspension cultures of soybean, wheat, purple foxglove, and jimsonweed and callus cultures of soybean and foxglove. In all species, nonextractable residues were found (soybean, jimsonweed, and foxglove suspensions, 14C; soybean and foxglove callus cultures, 20-25%; wheat, 30-40%); soluble metabolites were detected in only foxglove and wheat. About 90% of applied pyrene was transformed in wheat. Corresponding data from soybean and foxglove callus cultures were about 30% and those from soybean, jimsonweed, and foxglove suspensions about 7%. In foxglove, 1-hydroxypyrene methyl ether was identified as the main metabolite, whereas a complex mixture of carbohydrate conjugates of 1-hydroxypyrene was found in wheat. Due to the present results, crop and wild plants may be metabolic sinks for PAHs in the environment. Concentrations and toxicological implications of 1-hydroxypyrene, its derivatives, and analogous metabolites of other PAHs should be investigated.
- Hueckelhoven, Ralph,Schuphan, Ingolf,Thiede, Brigitte,Schmidt, Burkhard
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- Excited state intramolecular proton transfer in 1-hydroxypyrene
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1-Hydroxypyrene (1) shows unusual acid'base chemistry in its singlet excited state. Whereas most hydroxyarenes experience a marked enhancement in their acidity when excited, and rapidly deprotonate to give the corresponding phenolate anion, this is not an important pathway for 1, despite theoretical predictions that 1 should experience enhanced acidity as well. In this work, we demonstrate that 1 undergoes a competing excited state intramolecular proton transfer from the OH to carbon atoms at the 3, 6, and 8 positions of the pyrene ring to give quinone methide intermediates. When the reaction is carried out in D2O, reversion of these quinone methides to starting material results in replacement of the ring hydrogens with deuterium, providing a convenient handle to follow the reaction with NMR spectroscopy and mass spectrometry. The quantum yield for the reaction is 0.025 and appears to not be strongly dependent on the water content when aqueous acetonitrile solutions are used. 1-(2-Hydroxyphenyl) pyrene (19) was prepared and studied and shows similar reactivity to 1.
- Lukeman, Matthew,Burns, Misty-Dawn,Wan, Peter
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- A bispyrene derivative as a selective fluorescent probe for RNA
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A novel bispyrene compound was synthesized to selectively detect RNA through excimer emission "turn-on" in aqueous solution at physiological pH (7.4). The compound was used to successfully image RNA in HeLa cells.
- Liu, Yifan,Jun, Eun Jin,Kim, Gyoungmi,Lee, Ae-Ree,Lee, Joon-Hwa,Yoon, Juyoung
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- Synthesis of a new pyrene-devived fluorescent probe for the detection of Zn2+
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A novel pyrene-based receptor bearing benzothiazole was synthesized as a good turn-on fluorescent sensor for the recognition of Zn2+. The probe showed an excellent selectivity for Zn2+over most other competing ions (eg, Cr3+, Li+, Cd2+, Al3+, Pb2+, Li+, Mg2+, Ag+, Ca2+, Ni2+, Mn2+, Fe3+, Hg2+, Ba2+, K+, Na+, Cu2+, Fe2+) in EtOH-HEPES (65:35, v/v, pH = 7.20), which might be attributed to the photoinduced electron transfer (PET) mechanism. The formation of 1:1 stoichiometric PBZ-Zn2+ complex was determined based on the Job's plot, 1H NMR titration and ESI-MS. The binding constant of the complex was 4.04 × 104 M?1 with a detection limit of 2.58 × 10?7 M. The potential application of the PBZ in real water samples for recognizing Zn2+ was investigated. Bio-imaging study also revealed that PBZ could be applied to detecting Zn2+ in live cells. These results indicated that PBZ could be a favorable probe for Zn2+.
- Tang, Yanfeng,Huang, Yang,Lu, Linxia,Wang, Chun,Sun, Tongming,Zhu, Jinli,Zhu, Guohua,Pan, Jinyang,Jin, Yingli,Liu, Ailin,Wang, Miao
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- A selective 'Off-On' fluorescent sensor for Zn2+ based on hydrazone-pyrene derivative and its application for imaging of intracellular Zn2+
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A simple and effective fluorescent sensor based on hydrazone-pyrene has been synthesized. This probe displays a highly selective fluorescent enhancement with Zn2+, and application of this probe to detect the intrinsic Zn2+ ions present in pancreatic β-cells was successfully demonstrated.
- Zhou, Ying,Kim, Ha Na,Yoon, Juyoung
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- Cu2+-selective ratiometric and "off-on" sensor based on the rhodamine derivative bearing pyrene group
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A new rhodamine-based derivative bearing a pyrene group (PRC) was synthesized as a ratiometric and "off-on" chemosensor for Cu 2+. PRC displayed a selective and chelation enhanced ratiometric fluorescence change and colorlmetric change with Cu
- Zhou, Ying,Wang, Fang,Kim, Youngmee,Kim, Sung-Jin,Yoon, Juyoung
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- Method for preparing hydroxypyrene compound with high purity
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The present invention relates to a method for efficiently removing impurities while minimizing yield loss while minimizing yield loss of a hydroxy pyrene compound as a monomer for manufacturing a polymer compound for a hard mask having anti-reflection characteristics used in a lithographic process of a semiconductor manufacturing process. Pulene purification using pyrene (Pyrene) as starting material The present invention relates to a process for producing a high purity 1 -hydroxypyrene and a process for producing 1 -hydroxypyrene by reacting purified pyrene with a halogen compound under an appropriate solvent and catalyst, and a process for purifying 1 -hydroxypyrene.
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- Effects of substituents on absorption and fluorescence properties of trimethylsilylethynyl- and tert-butylethynyl-pyrenes
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Effects of substituents introduced at 1-position of trimethylsilylethynyl- and tert-butylethynyl-pyrenes on absorption and fluorescence properties were investigated. Fluorescence intensities of 1.0 × 10–5 M CH2Cl2 solutions of these pyrene derivatives were significantly larger than that of pyrene. Absorption of a silyl derivative having a formyl group shifted to longer wavelengths as the solvent polarity increased, whereas that of the carbon analog shifted to shorter wavelengths. On the other hand, in the solvent dependence of fluorescence, both fluorescence of them shifted to longer wavelengths as the polarity of the solvent increased. Fluorescence spectra of pyrene derivatives synthesized in this study at saturated concentrations in CH2Cl2 exhibited excimer emissions in the longer wavelength regions compared to that of unsubstituted pyrene. Fluorescence quantum yields of silicon analogs were higher than that of the corresponding carbon analogs in both solution and solid states. From the results of molecular orbital calculations, it was clarified that the effects of the substituents at the 1-position on the pyrene ring on the absorption and fluorescence properties can be explained by the properties of the molecular orbitals corresponding to the respective electron transitions.
- Furuyama, Taniyuki,Maeda, Hajime,Segi, Masahito,Ueno, Ryota
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- Pyrene-like methylthiopyridyl-2-(2- pyro-) Schiff base (Zn Schiff base) base2+ Preparation and application of fluorescent probe
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The invention relates to the field of a fluorescence probe, and particularly relates to preparation and application of a pyrenes 2-(2-methylthiopyridine)aniline Schiff base Zn fluorescence probe.The probe has the following concrete structure formula shown in the description. The fluorescence probe can be used for recognizing Zn in a methanol solution. The fluorescence probe has the advantages that the excellent selectivity is shown in other ion competition; higher fluorescence sensing property is realized; the detection limit is low; the sensitivity is high; the fluorescent quantum yield is high.
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Paragraph 0043; 0048-0051
(2019/12/25)
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- A General Strategy for Through-Bond Energy Transfer Fluorescence Probes Combining Intramolecular Charge Transfer: A Silyl Ether System for Endogenous Peroxynitrite Sensing
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A general strategy is reported for developing through-bond energy transfer (TBET) fluorescence probes by combining intramolecular charge transfer (ICT). The strategy uses a coplanar donor-π-bridge-acceptor system (SiOPh-PyOH) without spirolactam. The off-on switch of TBET and ICT is controlled by coplanar structure changes in the sensing process instead of spirolactam ring-opening in traditional TBET probes. DFT calculations showed that the energy and charge transfers from SiOPh to PyOH are prohibited. Since the SiOPh has no fluorescence, the probe SiOPh-PyOH shows fluorescence properties similar to that of pyrene. After sensing ONOO?, the silyl ether is removed and the probe changes into ?OPh-PyO?. Electron-donating ICT from OPh to PyO? induces a large redshift of emission to 594 nm (179 nm shift). TBET from OPh to PyO? ensures the probe exhibits a large pseudo-Stokes shift of 213 nm. Furthermore, the probe was successfully used in endogenous ONOO? detection. This study offers a new strategy for the construction of TBET probes emitting in the red region without spirolactam ring-opening, a new ONOO? sensing system using silyl ether as a reaction site, and a method for the deprotection of silyl ethers with ONOOH under mild conditions.
- Lu, Gonghao,Guo, Yuxin,Zhuo, Jiezhen,Li, Xue,Chi, Haijun,Zhang, Zhiqiang
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supporting information
p. 16350 - 16357
(2019/11/28)
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- A pyrene has mercapto ethylamine Schiff base Al3 + Fluorescent probe preparation and application thereof
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The present invention relates to the field of fluorescent probe, in particular to a pyrene has mercapto ethylamine Schiff base Al3 + Preparation and application of the fluorescent probe, specific structural formula as follows: The fluorescent probe can be in CH3 OH - H2 O (95:5, v/v, TRIS 10mmol/L, pH=7.40) solution identification Al3 + , Is: in competition with other ions appear in an excellent selectivity; has high fluorescence sensing nature; and low detection limit; high detection sensitivity, high fluorescence quantum yield.
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Paragraph 0041; 0046-0049; 0072; 0075; 0076
(2018/07/30)
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- A pyrene-based dual chemosensor for colorimetric detection of Cu2+ and fluorescent detection of Fe3+
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A pyrene based chemosensor was designed and synthesized. The pyrene fluorophore was connected with a pyridine unit through a Schiff base structure to give the sensor (L). L was tested with a variety of metal ions and exhibited high colorimetric selectivities for Cu2+ and Fe3+ over other ions. Upon binding with Cu2+ or Fe3+, L showed an obvious optical color change from colorless to pink for Cu2+ or orange for Fe3+ over a wide pH range from 3 to 12. Moreover, the fluorescence of L at 370 nm decreased sharply after bonding with Fe3+, while other metal ions including Cu2+ had no apparent interference. Thus, using such single chemosensor, Cu2+ and Fe3+ can be detected independently with high selectivity and sensitivity. The limits of detection toward Cu2+ and Fe3+ were 8.5 and 2.0 μM, respectively. DFT calculation results also proved the formation of stable coordination complexes and the phenomenon of fluorescence quenching by Fe3+. Furthermore, L was also successfully used as a bioimaging reagent for detection of Fe3+ in living cells.
- Guo, Yuxin,Wang, Lei,Zhuo, Jiezhen,Xu, Bo,Li, Xue,Zhang, Jianyu,Zhang, Zhiqiang,Chi, Haijun,Dong, Yan,Lu, Gonghao
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p. 3951 - 3956
(2017/09/26)
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- Preparation method of 1-pyrenol
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The invention relates to a preparation method of 1-pyrenol. The preparation method comprises the following steps of warming an alkyl sodium alkoxide solution for reflux, adding 1-bromine pyrene, performing a reaction for 10-15 hours, recovering a solvent, lowering the temperature, and performing centrifugal drying so as to obtain 1-alkoxyl pyrene; dissolving the 1-alkoxyl pyrene in the solvent, enabling the dissolved 1-alkoxyl pyrene and an amino acid compound containing tail-end sulfydryl to be subjected to a reaction under the condition of inorganic alkali and the temperature rising to 120-170 DEG C for 2-3 hours, recovering the solvent, performing purifying, and performing drying so as to obtain the 1-pyrenol. According to the 1-pyrenol prepared by the method disclosed by the invention, the content is 99%, and the yield is 88% or above.
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Paragraph 0019
(2017/07/20)
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- Synthesis, structure, and opto-electronic properties of regioisomeric pyrene-thienoacenes
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Three regioisomeric sulfur-bridged pyrene-thienoacenes (PTAs) have been synthesized. The crystal structures and optoelectronic properties of these ring-fused PTAs and their ring-opened precursors have been fully investigated. Among these isomers, the [3,4]-extended compound (4-S-PTA) shows the most pronounced spectral red-shift and highest quantum yield as well as large transistor mobility.
- Zhang, Shiqian,Qiao, Xiaolan,Chen, Ying,Wang, Yuanyuan,Edkins, Robert M.,Liu, Zhiqiang,Li, Hongxiang,Fang, Qi
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p. 342 - 345
(2014/04/03)
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- Novel bi-nuclear boron complex with pyrene ligand: Red-light emitting as well as electron transporting material in organic light-emitting diodes
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"Chemical Equation Presented" A novel boron complex bearing a pyrene ligand (CPB) was synthesized and Introduced as the first example of a binuclear boron complex In organic light-emitting diodes. In the solid state, CPB2 exhibited strong red emission. In the devices, red emission with Commission International de L'Eclairage (CIE) coordinates of (0,57, 0,42) was obtained by tuning the weight concentration of CPB2, CPB2 behaved as both an emitting and electron transporting material.
- Zhou, Ying,Kim, Ji Whan,Kim, Min Jung,Son, Won-Joon,Han, Su Jung,Kim, Ha Na,Han, Seungwu,Kim, Youngmee,Lee, Chongmok,Kim, Sung-Jin,Kim, Dong Ha,Kim, Jang-Joo,Yoon, Juyoung
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supporting information; scheme or table
p. 1272 - 1275
(2010/05/18)
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- Electrosynthesis of oligo(methoxyl pyrene) for turn-on fluorescence detection of volatile aromatic compounds
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A highly fluorescent conjugated oligomer, oligo(1-methoxyl pyrene) (OMOPr), was synthesized via electrochemical polymerization and its structure was studied by UV-vis spectroscopy, MALDI-TOF mass spectroscopy and ab initio calculation. The organic solutions of OMOPr emit strong blue lights and show solvatochromic effect, while these fluorescence emissions are quenched upon chain aggregation in its dry films. On the basis of these phenomena, a turn-on fluorescence sensor was fabricated and it can be used for detecting volatile aromatic compounds (VACs). The Royal Society of Chemistry.
- Gao, Yuanwei,Bai, Hua,Shi, Gaoquan
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scheme or table
p. 2993 - 2998
(2011/07/07)
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- Synthese d'analogues furanniques du benzopyrene
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We describe here the synthesis of 2-furan analogues of benzopyrene from 1-bromo-pyrene, i.e., pyrenofuran and pyrenofuran, as well as that of their derivatives bearing a nitro group on heterocycles.
- Demerseman, Pierre,Einhorn, Jacques,Gourvest, Jean-Francois,Royer, Rene
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- Photosubstitution and photoreduction of pyrene and 1-halopyrenes
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Upon irradiation, pyrene reacts with cyanide to give 1-cyanopyrene and with amide to give 1-aminopyrene.With oxygen nucleophiles no reaction takes place.Irradiation of pyrene in the presence of diethyl malonate anion yields 4,5,9,10-tetrahydropyrene in high yield, probably via initial electron transfer to excited pyrene. 1-Fluoropyrene can be photosubstituted with oxygen nucleophiles, leading to 1-hydroxy- and 1-methoxy-pyrene, in contrast to 1-chloro- and 1-bromo-pyrene, which are converted into a mixture of pyrene and 4,5-dihydropyrene upon irradiation.
- Tintel, C.,Rietmeyer, F. J.,Cornelisse, J.
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p. 224 - 228
(2007/10/02)
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