- Dithia[3.3]paracyclophane Core: A Versatile Platform for Triplet State Fine-Tuning and Through-Space TADF Emission
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Thermally activated delayed fluorescence (TADF) based on through-space donor and acceptor interactions constitute a recent and promising approach to develop efficient TADF emitters. Novel TADF isomers using a dithia[3.3]-paracyclophane building block as a
- Auffray, Morgan,Kim, Dae Hyeon,Kim, Jong Uk,Bencheikh, Fatima,Kreher, David,Zhang, Qisheng,D'Aléo, Anthony,Ribierre, Jean-Charles,Mathevet, Fabrice,Adachi, Chihaya
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- A two-photon fluorescent lipid raft probe derived from dicyanostilbene and similar to cholesterol’s structure
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Lipid raft is a microdomain being rich in cholesterol and sphingolipid and closely related to neurodegenerative diseases such as Alzheimer’s disease and prion disease. Hence the study on the physiological mechanism of lipid raft is helpful to reveal its biological role and its correlations with diseases. Two-photon fluorescence probe for lipid raft is a sharp tool to achieve this goal. A dicyanocarbazolylstilbene-derived two-photon fluorescence probe for lipid raft (DLR) was developed. Both DLR and lipid raft belong to D-π-A (donor-π-acceptor; π: C = C) type rigid planar molecule, and contain four fused carbon rings (one five-membered ring and three six-membered ring), and bear a long carbon chain (C8H17). The excellent comparability between the rigid plane of the probe molecule and the rigid lipid raft could significantly enhance the specific affinity to lipid rafts. DLR’s maximum emission wavelength increased with medium polarity while its fluorescence intensity (FI) augmented with viscosity, and FI in DPPC (dipalmitoylphosphatidylcholine) was 20 times higher than that in DOPC (dioleoylphosphatidylcholine). DLR’s fluorescence lifetime in DPPC was more than 2.2 times longer than that in DOPC. These indicate that DLR can distinguish DPPC from DOPC. Φδs of DLR in DPPC and DOPC were 1350 GM and 67 GM, respectively. DLR can image lipid raft distribution in cells and tissues. Graphic abstract: [Figure not available: see fulltext.]
- Huang, Chibao,Yang, Yuzhu,Li, Youfeng,Lv, Guoling
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p. 1223 - 1230
(2021/08/26)
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- Linear and V-shaped carbazole-based molecules functionalized by cyano acceptors and diversified donors: Synthesis, single- and two-photon related photophysical properties
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A series of novel linear and V-shaped carbazole-based molecules functionalized by cyano acceptors and diversified donors (carbazole, diphenylamino, dimethylamino, methoxy, and ferrocene) were synthesized and characterized by hydrogen-1 nuclear magnetic resonance, carbon-13 nuclear magnetic resonance, Fourier transform infrared spectroscopy, and high-resolution mass spectrometry. Their linear and nonlinear optical properties including UV–visible absorption, single-photon excited fluorescence, two-photon absorption, and frequency up-converted fluorescence, were systematically investigated in various solvents. The time-resolved photoluminescence studies using time-correlated single photon counting revealed their fluorescence lifetimes in THF. The solvent polarity exerts little effect on their absorption properties, while the emission properties (maximum fluorescence wavelength, Stokes shift, fluorescence quantum yield) display solvent polarity dependencies. Donor-acceptor functionalities and molecular dimensionality are considered to be the crucial structural factors that influence their optical properties. Pumped by a femtosecond laser (690–990 nm, 80 MHz, 140 fs), all the target molecules emit intense frequency up-converted fluorescence except FC1 and FC2 which contain one or two ferrocene donors. The two-photon absorption cross-sections in THF are in the range of 631–3014 GM. The density functional theory calculations were also conducted to unravel their electronic structures and to further understand the structure-property relationships. To our knowledge, this study is the first to be concerned with the single- and two-photon related photophysical properties of these D-π-A-π-D′ and D′-π-A-π-D-π-A-π-D′ carbazole-based molecules (D = donor, A = acceptor, π = conjugated bridge).
- Cai, Zhi-Bin,Liu, Shuang-Shuang,Li, Bo,Dong, Qi-Ji,Liu, Zi-Long,Zheng, Min,Li, Sheng-Li,Tian, Yu-Peng,Chen, Li-Jun,Ye, Qing
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p. 200 - 211
(2019/02/25)
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- Double-photon fluorescent probe used for temperature detection and derived from carbazole and preparation method of double-photon fluorescent probe
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The invention relates to the technical field of temperature probes, in particular to a double-photon fluorescent probe used for temperature detection and derived from carbazole and a preparation method of the double-photon fluorescent probe. The structural formula of the double-photon fluorescent probe is shown in the description. The fluorescence quantum yield of the probe is high, the detectionrange is wide, the application range of the double-photon fluorescent probe is greatly widened, and the detection reliability is improved.
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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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- Two-photon fluorescent sodium ion 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 a two-photon fluorescent sodium ion probe and its synthetic method and application, the probe in order to double-cyano stilbene is two-photon fluorescent matrix preparation. The probe molecules of small volume, to the sodium ion has very good selectivity, but zinc, potassium, calcium, magnesium, manganese, mercury and sodium ion other than the ion detection without interference, can detect micromolar concentration of the sodium ion. After the probe molecule complex sodium fluorescence intensity drop, sodium ion content can be two-photon fluorescence detection. Two-photon fluorescence microscopy imaging experiment shows the type of probe to the fibroblast like cells or tissue permeability, itself is not toxic to the cells, is especially suitable for the cell in the sodium ion concentration change and mercury ion distribution detection, in biological, in the medical field has great application value. (by machine translation)
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- Preparation method of two-photon fluorescence pH probe and application in cell imaging thereof
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The invention belongs to the technical field of fine chemical engineering, and particularly relates to a preparation method of a two-photon fluorescence pH probe and application in cell imaging thereof. The probe is prepared by taking dicyan-biphenyl-ethylene as a matrix, and comprises carbazolyl, di-cyano and n-octyl. Because the molecular structure of the probe has a longer flexible chain, the lipophicity is stronger, the probe can penetrate a cell wall (or cell membrane) into a cell to stain the cell for detecting the pH in the cell; the molecular structure of the probe belongs to D-pi-A type molecules, the two-photon absorption cross section (delta) is improved, so that the probe has higher imaging definition and resolution; in addition, the probe has a large Stokes shift in the marking process, thereby greatly improving the imaging accuracy and precision; the fluorescence quantum yield (phi) of the probe in a solvent is higher, the two-photon emission cross section is larger, so that the higher the brightness of the imaging is, the clearer the image is, and the higher the resolution is.
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- Cell in the mercury ion detection and for developing diphenyl ethylene bis-cyano benzene pair photon fluorescent probe
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The invention relates to a diphenylethene group dual cyano benzene two-photon fluorescence probe for detecting and displaying intracellular Hg ions, and the probe is prepared by performing nucleophilic substitution on mercaptoethanol and 2,5-di(4-[di(2-chloroethyl)amino]styryl)para-phthalonitrile. Laser excitation of 810nm can avoid photoinduced toxicity of cells. In a range of pH being 4.5-13, the probe has good selectivity on the Hg ions, and Na, K, Ca, Mg and Mn ions have no interference with detection, and the Hg ions of micro molarity can be detected. Fluorescence intensity is reduced after complexing of probe molecules and the Hg ions, and the content of the Hg ions can be subjected to two-photon fluorescence detection. A two-photon fluorescence microimaging experiment shows that the probe has good permeability on fibroblasts and other cells, has no toxic or side effects on the cells and is particularly suitable for the detection of intracellular Hg ion concentration change and Hg ion distribution.
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Paragraph 0039; 0040
(2017/08/25)
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- Open-Chain Crown-Ether-Derived Two-Photon Fluorescence Probe for Real-Time Dynamic Biopsy of Mercury Ions
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A novel two-photon fluorescence probe for Hg2+ derived from bis(styryl)terephthalonitrile, as a two-photon fluorophore, and bis[2-(2-hydroxyethyl sulfanyl) ethyl]amino group (ionophore), as a novel Hg2+ ligand, was developed. The probe possesses small molecule size, large two-photon absorption cross-section (1067 GM) in H2O, non-cytotoxic effect, long wavelength emission at 588nm, large Stokes shift (121nm), excellent photostability, high water solubility, good cell permeability, and pH insensitivity in the biologically relevant range. The probe can selectively detect Hg2+ ions in live cells and living tissues without interference from other metal ions and the membrane-bound probes, and its quenching constant is 8.73×105 M-1.
- Huang, Chibao,Zhang, Daohai,Qu, Junle,Liu, Xiaonan,Zhao, Guanglian,Yuan, Tingxiang,Liu, Yang
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p. 705 - 711
(2017/05/31)
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- Study of the interaction between 2,5-di-[2-(4-hydroxy-phenyl)ethylene]- terephthalonitril and bovine serum albumin by fluorescence spectroscopy
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A new compound, 2,5-di-[2-(4-hydroxy-phenyl)ethylene]-terephthalonitrile (DHPEPN), was synthesized. The interaction between bovine serum albumin (BSA) and DHPEPN in Tris-HCl buffer solution (pH 7.4) was investigated using fluorescence and UV-vis absorption spectroscopy. The mechanism of BSA fluorescence quenched by DHPEPN is discussed according to the Stern-Volmer equation. The binding constant and the thermodynamic parameters ΔH, ΔS, ΔG at different temperatures were calculated. The results indicate that the van der Waals interaction and hydrogen bonding play major roles in the binding process. The distance between BSA and DHPEPN is estimated to be 3.59 nm based on the Fo?rster resonance energy transfer theory. The spectral changes of synchronous fluorescence and three-dimensional fluorescence suggest that both of the microenvironment of DHPEPN and the conformation of BSA are changed during binding between DHPEPN and BSA.
- Zhang, Li-Na,Wu, Fang-Ying,Liu, Ai-Hong
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- Dicyanostilbene-derived two-photon fluorescence dyes with large two-photon absorption cross sections
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Four dicyanostilbene-derived two-photon fluorescence (TPF) dyes were synthesized as the model compounds to systematically study the effect of the dicyano and the terminal substituent on the two-photon absorption (TPA). These four compounds (DSO, DCY, DTO and DPH) exhibit very large two-photon absorption cross sections (δ). DCY (A-π-A) with the terminal cyano group has especially high fluorescence quantum yield (0.71) and relatively large δ (1480 GM), while DPH (D-π-A) with the substitutedamino group at its terminus possesses the largest δ (2800 GM) and the longest emission wavelength (620 nm). The idealest terminal substituent should not be the alkoxy group but the substitutedamino group. This class of dicyanostilbene dyes possess small molecule size, large δ (830-2800 GM), long-wavelength emission (459-620 nm) and large Stokes shift (80-206 nm), and are ideal chromophores for TPF labels and probes.
- Huang, Chibao,Lin, Changhua,Ren, Anxiang,Yang, Nianfa
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- Dicyanostilbene-derived two-photon fluorescence probe for free zinc ions in live cells and tissues with a large two-photon action cross section
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A novel two-photon fluorescence probe for Zn2+ derived from dicyanostilbene as a two-photon fluorophore and 4-(pyridine-2-ylmethyl) piperazine as a novel Zn2+ ligand was developed. The probe shows a 72.5-fold fluorescence enhancement in response to Zn2+, a large two-photon action cross-section (580 GM), a noncytotoxic effect, and pH insensitivity in the biologically relevant range, and its dissociation constant (KdTP) is 0.52 ± 0.01 μM. The probe can selectively detect free Zn2+ ions in live cells for 1500 s or so and in living tissues at a depth of 80-150 μm without interference from other metal ions and the membrane-bound probes.
- Huang, Chibao,Qu, Junle,Qi, Jing,Yan, Meng,Xu, Gaixia
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scheme or table
p. 1462 - 1465
(2011/06/21)
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- Red light emitting compounds for organic electroluminescent devices and organic electroluminescent devices using them
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The present invention relates to red color emitting compounds for an organic electroluminescent device (OELD), particularly to red color emitting compounds represented by the following formula (1) having high luminescence efficiency and enhanced thermal-s
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- A novel series of copolymers containing 2,5-dicyano-1,4- phenylenevinylene - Synthetic tuning of the HOMO and LUMO energy levels of conjugated polymers
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A series of copolymers of 2,5-dicyano-1,4-phenylenevinylene and 2- methoxy-5-(2'-thylhexyloxy)-1,4-phenylenevinylene were synthesized by Wittig reaction. The HOMO and LUMO energy levels of copolymers can be easily tuned by controlling the feed ratio of co
- Xiao,Yu,Chua,Huang
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p. 1318 - 1321
(2007/10/03)
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- A Selective Receptor for Arginine Derivatives in Aqueous Media. Energetic Consequences of Salt Bridges That Are Highly Exposed to Water
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Quantitative measures of salt-bridge-type interactions in a highly exposed aqueous environment have been obtained by modifying the well-studied cyclophane platform 1 to include carboxylates in close proximity to bound, cationic guests, producing hosts 2 and 3. Many guests show significantly enhanced binding to 2 and 3, but cations of the RNMe3+ type show little or no enhancement. We propose that the latter observations result from the fact that RNMe3+ compounds have very diffuse positive charges. Guests that show enhanced binding have focused regions of large, positive electrostatic potential. The highly charged 3 is able to bind very polar, very well-solvated guests, including a series of arginine-based dipeptides. Neutral, water-soluble host 4 was prepared and found to show a decreased affinity for cationic guests. We propose a novel induced dipole mechanism to rationalize these results.
- Ngola, Sarah M.,Kearney, Patrick C.,Mecozzi, Sandro,Russell, Keith,Dougherty, Dennis A.
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p. 1192 - 1201
(2007/10/03)
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- Substituent Effect of 1,4-Benzenedicarbonitriles as Sensitizers on the Photoinduced Electron Transfer Reactions in Alcohol
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In the photosensitized electron transfer reaction of 6,6-diphenyl-1,4-dioxaspiro[4.5]decane in methanol (MeOH), the quantum yield is increased by the use of 2-methylbenzene-1,4-dicarbonitrile (2-methyl-BDC) or 2,5-dirnethylbenzene-1,4-dicarbonitrile (2,5-
- Suzuki, Masanori,Ikeno, Taketo,Osoda, Kazuhiko,Narasaka, Koichi,Suenobu, Tomoyoshi,Fukuzumi, Shunichi,Ishida, Akito
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p. 2269 - 2277
(2007/10/03)
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- Preparation of 1,4-Dicyanobenzene Derivatives and the Substituent Effect of the Sensitizers on Photoinduced Electron-Transfer Reactions
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Substituted 1,4-dicyanobenzenes are prepared as electron-accepting photosensitizers.The efficiency of some photosensitized reactions is influenced remarkably by the substituent(s) of 1,4-dicyanobenzene.By using mono or dimethylated dicyanobenzene, the rea
- Osoda, Kazuhiko,Pannecoucke, Xavier,Narasaka, Koichi
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p. 1119 - 1120
(2007/10/03)
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