90134-10-4Relevant articles and documents
Novel yellow- to red-emitting fluorophores: Facile synthesis, aggregation-induced emission, two-photon absorption properties, and application in living cell imaging
Dong, Qi-Ji,Cai, Zhi-Bin,Ding, Ling,Luo, Pei-Hua,He, Qiao-Jun,Li, Sheng-Li,Chen, Li-Jun,Ye, Qing,Tian, Yu-Peng
, (2020/10/29)
Four novel yellow-to red-emitting fluorophores with a 1-(2-hydroxyethyl) pyridinium core and different electron-donating terminal moieties (N-methylcarbazole, N,N-dibutylbenzenamine, N-methylpyrrole, and 2-methylfuran) were designed and facilely synthesized via the one-step Knoevenagel condensation. All these compounds (HPs) were characterized by 1H NMR, 13C NMR, and HRMS. Their photophysical properties including linear absorption, one-photon excited fluorescence, two-photon absorption, and two-photon excited fluorescence, were systematically investigated in various solvents. And the density functional theory calculations were conducted to analyze the electronic structures of HPs. The two-photon absorption cross-sections (δ) values of HPs measured by the Z-scan technique were determined to be as large as 1354 (1HP-CZ), 4462 (2HP-BA), 836 (3HP-PR), and 2944 GM (4HP-FU) in DMSO. The two-photon action cross-sections (Φ × δ) values of 1HP-CZ and 2HP-BA in H2O measured by the two-photon induced fluorescence method were about 50 GM. 1HP-CZ, 3HP-PR, and 4HP-FU also exhibited good water solubility. Meanwhile, it was found that 2HP-BA exhibited notable aggregation-induced emission characteristic in DMSO/H2O mixture. The aggregate particle size distribution of 2HP-BA was measured by the dynamic light scattering method, and the aggregation characteristic of 2HP-BA was observed by the transmission electron microscopy. Besides, 2HP-BA also exhibited red emission. Then, HPs with relatively low cytotoxicity were used for one- and two-photon excited fluorescence imaging in living HepG2 cells. The results indicate that HPs are potential candidates in the bioimaging field due to their photophysical properties and biocompatibility.
Mn (II) complex with AIE property and function of targeting living cell mitochondria as well as preparation method and application of Mn (II) complex
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Paragraph 0029-0030, (2021/08/06)
The invention discloses a Mn (II) complex with AIE property and a function of targeting living cell mitochondria as well as a preparation method and application of the Mn (II) complex, and relates to the technical field of multiphoton absorption materials
3-hydroxy flavone compound and application thereof
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Paragraph 0043; 0047; 0048; 0050; 0055-0057; 0058, (2019/11/28)
The invention belongs to the technical field of biological fluorescence analysis, and particularly relates to a 3-hydroxy flavone compound and an application thereof. The compound is particularly a 4-n,n-dialkylamino-3-hydroxy flavone compound, and when the compound is used as a fluorescent dye, the lipid droplet targeting property is better, and a cytoskeleton is hardly colored. When conjugated structures such as a benzene ring and the like are added to the left side of a molecule of the compound, the emission wavelength of the molecule can be greatly prolonged, and fluorescence crossing of the molecule from yellow to red is realized. The compound can be applied to the aspects of dynamic lipid droplet imaging in cells, lipid droplet growth process imaging, adipose tissue imaging, even simultaneous imaging of intramuscular fat and intermuscular fat in skeletal muscle tissues, and the like, and has important application values in the fields of fluorescent dyes, biological fluorescent labels and the like.
Aminostyrylpyridinium-salt fluorescent monomer and preparing and application of polymer of aminostyrylpyridinium-salt fluorescent monomer
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, (2017/07/21)
The invention relates to an aminostyrylpyridinium-salt fluorescent monomer, a synthesis method of a polymer of the aminostyrylpyridinium-salt fluorescent monomer and application prospects of the water-soluble fluorescent polymer in the field of oil fields. The fluorescent monomer structure is shown as the formula (I) (please see the specification). The synthesis method includes the steps that 4-methylpyridine and alkyl halide are subjected to an alkylation reaction to generate 4-methylpyridine salt, aniline is subjected to a N-alkylation reaction or an acylation reaction and then subjected to a Vilsmeier reaction, an aldehyde group is led in a para-position mode, and finally, the aldehyde group and methyl of the 4-methylpyridine salt are condensated to generate the aminostyrylpyridinium-salt fluorescent monomer. The fluorescent monomer and water-soluble monomers such as acrylamide, acrylic acid, methacrylamide, methylpropanesulfonic acid, N,N-dimethylacrylamide and N,N-diethylacrylamide are subjected to binary polymerization or terpoly polymerization, and a water-soluble fluorescent tracing polymer is prepared. The fluorescent tracing polymer can be applied to concentration detection of the polymer through polymer flooding.
Monocarboxylate transporter 1 inhibitors as potential anticancer agents
Gurrapu, Shirisha,Jonnalagadda, Sravan K.,Alam, Mohammad A.,Nelson, Grady L.,Sneve, Mary G.,Drewes, Lester R.,Mereddy, Venkatram R.
, p. 558 - 561 (2015/05/27)
Potent monocarboxylate transporter 1 inhibitors (MCT1) have been developed based on α-cyano-4-hydroxycinnamic acid template. Structure-activity relationship studies demonstrate that the introduction of p-N, N-dialkyl/diaryl, and o-methoxy groups into cyanocinnamic acid has maximal MCT1 inhibitory activity. Systemic toxicity studies in healthy ICR mice with few potent MCT1 inhibitors indicate normal body weight gains in treated animals. In vivo tumor growth inhibition studies in colorectal adenocarcinoma (WiDr cell line) in nude mice xenograft models establish that compound 27 exhibits single agent activity in inhibiting the tumor growth.
Asymmetrically Substituted and π-Conjugated 2,2′-Bipyridine Derivatives: Synthesis, Spectroscopy, Computation, and Crystallography
Bodapati, Ramakrishna,Sarma, Monima,Kanakati, Arunkumar,Das, Samar K.
, p. 12482 - 12491 (2016/01/09)
A new series of monosubstituted styryl- and bistyryl-2,2′-bipyridine luminophores (compounds 16-23) have been synthesized via Horner-Wadsworth-Emmons reaction involving a monophosphonate and donor aromatic aldehydes. In the title chromophores, the amino donors are varied between acyclic and cyclic while the alkoxy donors are varied in terms of their number and position. The absorption maxima of these chromophores shift predominantly due to intramolecular charge transfer (ICT) between different donor and acceptor moieties. The title donor-acceptor molecules exhibit intense fluorescence in solution at room temperature, and their emissive behavior has been found to be highly sensitive to solvent polarity. The fluorescence spectra and quantum yields of all the chromophores were recorded in four different solvent media, and the chromophores 16, 17, 19, and 21 exhibit fluorescence in the solid state too. The influence of the nature and position of the donor functionalities in the conjugated backbone of the bipyridine moiety on the electronic absorption properties of the title chromophores (16-23) has been demonstrated, which has further been corroborated by DFT and TD-DFT computation both in gas phase and in solution phase. The crystal structure of compound 18 has been described as a representative member of the family (16-23).
New Aggregation-Induced Emitters: Tetraphenyldistyrylbenzenes
Freudenberg, Jan,Rominger, Frank,Bunz, Uwe H. F.
, p. 16749 - 16753 (2015/11/16)
The synthesis of five novel distyrylbenzene (DSB) derivatives, featuring a central tetraphenylbenzene core, is reported. The targets show aggregation-induced emission (AIE), which, however, is substituent-dependent. For the pure hydrocarbon and derivative
Cruciform 9,10-distyryl-2,6-bis(p-dialkylamino-styryl)anthracene homologues exhibiting alkyl length-tunable piezochromic luminescence and heat-recovery temperature of ground states
Zheng,Zhang,Sun,Li,Liu,Xue,Yang
, p. 1913 - 1920 (2014/03/21)
A series of 2,6-bis(p-dialkylaminostyryl)-9,10-distyrylanthracene (FCn) cruciforms with N-alkyl chains of different lengths have been synthesized, and their aggregation-enhanced fluorescence and piezochromic luminescence (PFC) behaviours are investigated. These 9,10-distyrylanthracene-containing cruciforms exhibit relatively low fluorescence quantum yields (Φ) in THF solution (Φ ≈ 10%) and moderate aggregation-enhanced emission in aqueous media (Φ ≈ 25%), but strong and chain length-dependent solid-state fluorescence emission. Grinding and pressing experiments indicate that they are all effective PFC materials in terms of mechanical stress-induced spectral shifts (ΔλPFC = 23-54 nm), moreover, the longer alkyl-containing FCn shows a larger ΔλPFC. Powder X-ray diffraction and differential scanning calorimetry measurements reveal that the transformation between the crystalline and amorphous states upon external stimuli is responsible for the reversible PFC behaviour. It is found that increasing the N-alkyl length could effectively decrease the cold-crystallization temperature of the ground states to render the PFC states with a tunable heat-recovering temperature, and ground FC10 and FC12 solids can recover spontaneously to their original states at room temperature.
Relationship between molecular stacking and optical properties of 9,10-bis((4-N,N-dialkylamino)styryl) anthracene crystals: The cooperation of excitonic and dipolar coupling
Li, Feng,Gao, Na,Xu, Hai,Liu, Wei,Shang, Hui,Yang, Wenjun,Zhang, Ming
, p. 9991 - 9997 (2014/08/18)
Five 9,10-bis((4-N,N-dialkylamino)styryl) anthracene derivatives (DSA-C1-DSA-C7) with different length alkyl chains were synthesized. They showed the same color in dilute solutions but different colors in crystals. The absorption, photoluminescence, and fluorescence decay indicate that there exist both excitonic and dipolar coupling in crystals of DSA-C1-DSA-C7. X-ray crystallographic analysis revealed that all the crystals belong to the triclinic space group P1 with one molecule per unit cell and that the molecules in every crystal have the identical orientation. This offers ideal samples to investigate the impact of the molecular stacking on the optical properties of the crystals. For the first time, the cooperation of excitonic and dipolar coupling has been comprehensively studied, and the contribution to the spectral shift from the excitonic and dipolar couplings quantitatively obtained. The experiments of amplified spontaneous emission (ASE) together with measurements of the quantum efficiency further confirmed this interpretation. The results suggest that the excitonic and dipolar couplings between the adjacent molecules are both important and jointly induce the spectral shifts of the crystals.
D-π-A-A-π-D prototype 2,2′-bipyridine dyads exhibiting large structure and environment-sensitive fluorescence: Synthesis, photophysics, and computation
Sarma, Monima,Chatterjee, Tanmay,Ghanta, Susanta,Das, Samar K.
, p. 432 - 444 (2012/02/16)
A series of 4,4′-π-conjugated-2,2′-bipyridine chromophores (MS 1-8) were synthesized, and their photophysical and thermal properties were investigated. The title "push-pull' chromophores", except MS 1, were integrated with both alkoxy and alkylamino donor functionalities that differ in their donation capabilities. The oligophenylenevinylene (OPV) chromophores MS 4-8 are associated with a π-extended backbone in which the position and the number of alkoxy donors were systematically varied. All of the studied systems possess a D-π-A-A-π-D dyad archetype in which the A-A is the central 2,2′-bipyridine acceptor core that is electronically attached with the donor termini through π-linkers. The fluorescence quantum yields of the synthesized chromophores are found to be sensitive to the molecular archetype and the solvent medium. Out of the eight fluorescent compounds reported in this article, the compound MS 5 exhibits fluorescence in the solid state also. The modulating effect of the nature, position, and number of donor functionalities on the optical properties of these classes of compounds has further been comprehended on the basis of DFT and TD-DFT computation in a solvent reaction field.
