- New BODIPY derivatives as OFF-ON fluorescent chemosensor and fluorescent chemodosimeter for Cu2+: Cooperative selectivity enhancement toward Cu2+
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New 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) derivatives (1 and 2) were synthesized as an "off-on" fluorescent chemosensor and fluorescent chemodosimeter for Cu2+ and Pb2+. Compound 1 displayed selective and large chelation enhanced fluorescence effects with Pb2+ and Cu2+ among the metal ions examined. On the other hand, compound 2, a fluorescent chemodosimeter, effectively recognized Cu 2+ via a selective hydrolysis of the acetyl group.
- Qi, Xin,Jun, Eun Jin,Xu, Li,Kim, Sung-Jin,Hong, Jay Sung Joong,Yoon, Yeo Joon,Yoon, Juyoung
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- Precious metal-free molecular machines for solar thermal energy storage
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Four benzothiazolium crown ether-containing styryl dyes were prepared through an optimized synthetic procedure. Two of the dyes (4b and 4d) having substituents in the 5-position of the benzothiazole ring are newly synthesized compounds. They demonstrated a higher degree of trans-cis photoisomerization and a longer life time of the higher energy forms in comparison with the known analogs. The chemical structures of all dyes in the series were characterized by NMR, UV-vis, IR spectroscopy and elemental analysis. The steady-state photophysical properties of the dyes were elucidated. The stability constants of metal complexes were determined and are in good agreement with the literature data for reference dyes. The temporal evolution of trans-to-cis isomerization was observed in a real-time regime. The dyes demonstrated a low intrinsic fluorescence of their Ba2+ complexes and high yield of E/Z photoisomerization with lifetimes of the higher energy form longer than 500 seconds. Density functional theory (DFT) calculations at the B3LYP/6-31+G(d,p) level were performed in order to predict the enthalpies (H) of the cis and trans isomers and the storage energies (ΔH) for the systems studied.
- Kandinska, Meglena I.,Kitova, Snejana M.,Videva, Vladimira S.,Stoyanov, Stanimir S.,Yordanova, Stanislava B.,Baluschev, Stanislav B.,Angelova, Silvia E.,Vasilev, Aleksey A.
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p. 1096 - 1106
(2019/06/08)
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- Double-cyano stilbene ethylene two-photon fluorescent solvent chromophore water-soluble probe and its synthetic method and application (by machine translation)
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The invention belongs to the technical field of fine chemicals, in particular to double-cyano stilbene ethylene two-photon fluorescent solvent chromophore water-soluble probe and its synthetic method and application, the probe in order to double-cyano stilbene (DCS) for the two-photon fluorescent matrix preparation. The probe molecules of small size, good solubility in water and is suitable for solvent polarity detection, in addition to the fluorescence intensity of the probe, two-photon absorption cross section of the insured with viscosity changes obviously, display a very wide range of solvent chromophore, large two-photon absorption cross section and ultra-large Stokes displacement, thereby greatly improving the detection sensitivity, imaging resolution, sensitivity and transverse and longitudinal resolution, and the accuracy of the test; cell microscopic imaging experiment to demonstrate that its in a cell or tissue has good color range and absorption effect, can be very good detection and reflect cell change in viscosity of the situation, and itself not toxic to the cells. In biological, in the medical field has great application value. (by machine translation)
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- A fluorene-based material containing triple azacrown ether groups: Synthesis, characterization and application in chemosensors and electroluminescent devices
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We design a novel multifunctional fluorene-based material containing triple azacrown ether (FTC) not only for application in aqueous solution as a chemosensor towards Fe3+ but also to enhance the electroluminescence of PLEDs using an environmentally stable aluminum cathode. The photo-physical and sensing properties were investigated by absorption and photoluminescence (PL) spectroscopy. The FTC exhibited specific selectivity and high sensitivity toward Fe3+, with the Stern-Volmer coefficients (Ksv) being 1.59 × 105 M-1 in a solvent mixture of tetrahydrofuran and water (THF-H2O = 9/1, v/v). The FTC maintained high selectivity toward Fe3+ in the presence of ten interfering metal cations. The HOMO and LUMO levels were estimated to be -5.88 eV and -2.88 eV, respectively. The FTC significantly enhances the emission performance of PLEDs [ITO/PEDOT:PSS/MEH-PPV/EIL/Al] when used as an electron injection layer (EIL), especially in the presence of metal carbonates. Particularly, the device using K2CO3 doped FTC as the electron-injection layer (EIL) exhibited significantly enhanced performance compared to the one without EIL. The performance was significantly enhanced to 11630 cd m-2 and 1.47 cd A-1, respectively, from 230 cd m-2 and 0.03 cd A -1 of the non-FTC device. Current results indicate that multifunctional fluorene-based material FTC is a potential candidate for selective detection of Fe3+ and as an effective electron injection layer to enhance the performance of MEH-PPV.
- Wu, Chia-Shing,Lin, Ying-Ju,Chen, Yun
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p. 1419 - 1429
(2014/03/21)
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- Water/alcohol soluble electron injection material containing azacrown ether groups: Synthesis, characterization and application to enhancement of electroluminescence
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Using an environmentally stable metal as the cathode in a polymer light-emitting diode (PLED) is an essential requirement for its practical application. We present the preparation of a water/alcohol soluble copoly(p-phenylene) (P1) containing pendant azacrown ether and ethylene glycol ether groups as a highly efficient electron injection layer (EIL) for PLEDs, allowing the use of environmentally stable aluminum as the cathode. Multilayer PLEDs [ITO/PEDOT:PSS/PF-Green-B/EIL/Al] using P1 as EIL exhibit significantly enhanced device performance, particularly in the presence of K 2CO3 or Cs2CO3. The maximum luminous power efficiency and maximum luminance of the device with Cs2CO 3-doped P1 as EIL were enhanced to 9.16 lm W-1 and 17050 cd m-2, respectively, compared with those without EIL (0.16 lm W -1, 890 cd m-2). The turn-on voltage was also significantly reduced from 5.7 V to 3.7 V simultaneously. The performance enhancement has been attributed to improved electron injection which has been confirmed by the rise in open-circuit voltage (Voc) obtained from photovoltaic measurements. The incorporation of such an electron injection layer significantly enhances device performance for PLEDs with an environmentally stable metal as the cathode.
- Wu, Chia-Shing,Lu, Huai-An,Chen, Chiao-Pei,Guo, Tzung-Fang,Chen, Yun
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p. 1430 - 1439
(2014/03/21)
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- Copoly(p-phenylene) containing azacrown ether: Synthesis, optical properties, and application for chemical sensor
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Copoly(p-phenylene) (P1) containing pendent azacrown ether and ethylene glycol ether was prepared by the Suzuki coupling reaction and applied for chemical sensor. Poly(p-phenylene) derivative P0 without the azacrown ether groups were also synthesized for comparative study. The photophysical and sensing properties were investigated by absorption and photoluminescence (PL) spectroscopy to elucidate the influence of the azacrown ether groups. The P1 exhibited specific selectivity and high sensitivity toward Zn2+, with the Stern-Volmer coefficient (Ksv) being 3.66 × 106 M-1 at low concentration in mixture solvent of tetrahydrofuran and water (THF/H2O = 9/1, v/v). The P1 maintained high selectivity toward Zn2+ in the presence of fifteen interfering metal cations. This results indicate that copoly(p-phenylene) (P1) is a promising functional material for chemical sensors. Copyright
- Wu, Chia-Shing,Chen, Chiao-Pei,Chen, Yun
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p. 3975 - 3984
(2013/09/02)
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- Aminostilbazolium derivatives substituted by hydroxyethyl groups for second-order nonlinear optics
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As DAST (1-methyl-4-{2-[4-(dimethylamino)phenyl]ethenyl}pyridinium p-toluenesulfonate) derivatives for improved crystal stability and inhibition of crystal water inclusion, 1-(2-hydroxyethyl)-4-(2-{4-[bis(2-hydroxyethyl)amino] phenyl}ethenyl)pyridinium salts 2 (2a-2l) and 1-(2-hydroxyethyl)-4-{2-[4- (diethylamino)phenyl]ethenyl}pyridinium salts 3 (3a-3l) were synthesized and their properties were investigated. Salts 3 were found to have no crystal water, and the cation with one hydroxyethyl group was effective to eliminate water inclusion in the crystals. Although the melting points of 2 were lower than those of the corresponding 3, decomposition temperatures of these chromophores were above 250°C indicating their good thermal stability. Crystals of m-nitrobenzenesulfonate salt 3f was obtained without crystal water and showed SHG activity. Copyright Taylor & Francis Group, LLC.
- Ikeda, Takahiro,Tadaki, Yui,Funajima, Ryo,Tatewaki, Yoko,Okada, Shuji
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scheme or table
p. 482 - 487
(2011/12/01)
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- Colorimetric probes based on anthraimidazolediones for selective sensing of fluoride and cyanide ion via intramolecular charge transfer
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Probes based on anthra[1,2-d]imidazole-6,11-dione were designed and synthesized for selective ion sensing. Each probe acted as strong colorimetric sensors for fluoride and cyanide ions and exhibited intramolecular charge transfer (ICT) band, which showed significant red-shifts after addition of either the F- or CN- ion. One of the probes (2) showed selective colorimetric sensing for both cyanide and fluoride ions. In organic medium, 2 showed selective color change with fluoride and cyanide, whereas in aqueous organic medium it showed a ratiometric response selectively for cyanide ion.
- Kumari, Namita,Jha, Satadru,Bhattacharya, Santanu
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experimental part
p. 8215 - 8222
(2012/01/03)
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- Near-infrared solid-state emitters based on isophorone: Synthesis, crystal structure and spectroscopic properties
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A series of near-infrared solid-state emitters based on the dicyanoisophorone electron acceptor group was synthesized. The solid-state spectroscopic properties were studied by UV-visible absorption spectroscopy and fluorescence spectroscopy and analyzed i
- Massin, Julien,Dayoub, Wissam,Mulatier, Jean-Christophe,Aronica, Christophe,Bretonniere, Yann,Andraud, Chantal
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experimental part
p. 862 - 873
(2012/02/14)
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- Synthesis, spectroscopy and photochemistry of novel branched fluorescent nitro-stilbene derivatives with benzopheonone groups
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In this article, we presented novel nitro-stilbene derivatives with one or two benzophenone groups as photoinitiators via multi-steps synthesis. The ultraviolet/visible spectroscopy and the emission spectroscopy of the compounds were determined in various solvents. The results showed that the ultraviolet/visible absorption spectroscopy of the derivatives with benzophenone moiety displayed overlap effects of nitro-stilbene and benzophenone parts. In non-polar solvents, the derivatives exhibited strong emission, while they displayed weak emission in modest and strong polar solvents. Dyes-linked benzopheonone groups displayed stronger fluorescence emission than simple chromophore parent molecules. Visible-light photoinitiating effects of the derivatives were investigated extensively. Methyl methacrylate could be photoinitiated efficiently by the derivatives with benzophenone moieties at very low concentration, even at 1×10-5 mol/ L. While the photopolymerization efficiency of styrene initiated by the derivatives was lower than that of methyl methacrylate. Our results showed that the dye-linked photoinitators had more efficient photoinitiating than the simple mixture of dye and photoinitator. Furthermore, the derivative with two benzophenone groups displayed more excellent phototiniatiating effects than the derivative with one benzophenone group. Thermodynamics driving for the occurrence of visible-light photoinduced intramolecular electron transfer from chromophore part to benzophenone part was evaluated. Benzopinacol moiety produced in photoreaction was confirmed by nuclear magnetic resonant spectroscopy. Thermal stability of the derivatives was analyzed. Springer Science+Business Media, LLC 2010.
- Gao, Fang,Liu, Jian,Peng, Huayong,Hu, Nvdan,Li, Hongru,Zhang, Shengtao
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p. 703 - 712
(2011/10/31)
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- Synthesis and HIV-1 integrase inhibition of novel bis- or tetra-coumarin analogues
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Present studies were undertaken on the preparation of synthetic analogues of bis- or tetra-coumarins and their activity against HIV-1 integrase (HIV-1 IN). Among these coumarin analogues, compounds 14, 16 and 18 were found to be potent molecules against HIV-1 IN at IC50 values of 0.96, 0.58, and 0.49 μM, respectively. The results provided a tool for guiding the further design of more potent antiviral agents and for predicting the affinity of related compounds.
- Chiang, Chih-Chia,Mouscadet, Jean-Francois,Tsai, Hou-Jen,Liu, Chi-Tsan,Hsu, Ling-Yih
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p. 1740 - 1743
(2008/09/20)
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- The synthesis of highly active thiophene ring-containing chromophore components for photonic polymers based on a newly designed route
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2-Aminothiophene derivatives are the key intermediates for the present synthesis. It is known that the synthesis of 2-aminothiophene is troublesome although it is a rather simple heterocycle. In this work, an early report was newly developed as a basis for the efficient synthesis of thiophene-ring-containing chromophore components for photonic polymers. 2-Amino-5-nitrothiophene and 2-amino-3,5-dinitrothiophene were synthesized in excellent yield. After diazotization, the 2-aminothiophene derivatives were directly treated with N-phenyldiethanolamine to afford two-electron push-pull compounds. A similar styryl compound was also prepared. All of these chromophore molecules have further polymerizable hydroxy groups on one end of the molecule. These compounds are currently showing interesting potential in making highly sensitive, nonlinear optical polymeric materials. The Royal Society of Chemistry 1999.
- Yuquan, Shen,Yuxia, Zhao,Zao, Li,Jianghong, Wang,Ling, Qiu,Shixiong, Liu,Jianfeng, Zhai,Jiayun, Zhou
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p. 3691 - 3695
(2007/10/03)
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- Synthesis and coordination studies of new mono- and di-hydroxy functionalized 4,4'-dialkenyl-2,2'-bipyridines
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A convenient and large scale preparation of new mono- and bis-hydroxy substituted 4,4'-bis(dialkylammostryl)-2,2'-bipyridimes is reported. Their coordination studies to [Ru(DEAS-bpy)2]2+ (DEAS-bpy = 4,4'- bis(diethylaminostyryl)-2,2'-bipyridine) are also described.
- Le Bouder, Thomas,Massiot, Philippe,Le Bozec, Hubert
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p. 6869 - 6872
(2007/10/03)
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- Synthesis, characterization and properties of NLO dye-containing polyurethane
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Polyurethane attached hemicyanine dye with tetraphenylborate anion was synthesized. This polymer was soluble in dimethylformamide and could be processed into thin film by spin coating. The poled polymer film showed a large second-order nonlinear optical coefficient (χ(2) = 4.0×10-7 esu) and good temporal stability.
- Moon,Shim,Lee
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