- A General Strategy for the Construction of NIR-emitting Si-rhodamines and Their Application for Mitochondrial Temperature Visualization
-
Si-rhodamine (SiR) is an ideal fluorophore because it possesses bright emission in the NIR region and can be implemented flexibly in living cells. Currently, several promising approaches for synthesizing SiR are being developed. However, challenges remain
- Tang, Weiguo,Gao, Han,Li, Jiaxin,Wang, Xianhui,Zhou, Zhikuan,Gai, Lizhi,Feng, Xin Jiang,Tian, Jiangwei,Lu, Hua,Guo, Zijian
-
-
Read Online
- Bioorthogonal double-fluorogenic siliconrhodamine probes for intracellular super-resolution microscopy
-
A series of double-fluorogenic siliconrhodamine probes were synthesized. These tetrazine-functionalized, membrane-permeable labels allowed site-specific bioorthogonal tagging of genetically manipulated intracellular proteins and subsequent imaging using s
- Kozma,Estrada Girona,Paci,Lemke,Kele
-
-
Read Online
- AZO COMPOUND AND TEXTILE PRINTING METHOD
-
To provide a dye having good light fastness and used for various recording media, preferably for fiber, and further preferably for polyester fiber.SOLUTION: The present invention provides a compound represented by the formula (1) in the figure. (In the formula (1), R1 represents a hydrogen atom or nitro group; R2 and R3 each independently represent a C1-C4 alkyl group optionally substituted with a C1-C4 alkoxy group or phenyl group; R4 represents a halogen atom; and R2 and R3 may be linked to each other to form a ring.)SELECTED DRAWING: None
- -
-
Paragraph 0078-0079
(2021/02/25)
-
- COLORANT DISPERSION LIQUID AND PRINTING METHOD OF HYDROPHOBIC FIBER
-
PROBLEM TO BE SOLVED: To provide black dispersion liquid for inkjet printing ink that can manufacture a dyed thing excellent in color rendering, can obtain high quality dyed thing that can obtain high concentration dyed thing, and has excellent redispersion. SOLUTION: A colorant dispersion comprises (A) a compound expressed by a formula (1), and (B) polyoxyethylene arylphenyl ether-based dispersant and polyoxyethylene arylphenyl ether sulfate-based dispersant. (R1 is H or a nitro group; R2 and R3 are independently C1 to C4 alkoxy group or C1 to C4 alkyl group that may be substituted with a phenyl group; R4 is halogen atom; and R2 and R3 may be mutually coupled to form a ring.) SELECTED DRAWING: None COPYRIGHT: (C)2021,JPOandINPIT
- -
-
Paragraph 0096-0097
(2021/08/13)
-
- COLORED DISPERSION, INK COMPOSITION USING THE SAME, AND DISPERSION STABILITY IMPROVEMENT METHOD THEREWITH AND PRINTING METHOD OF HYDROPHOBIC FIBER
-
PROBLEM TO BE SOLVED: To provide dispersion liquid for inkjet printing ink that can manufacture a dyed thing excellent in color rendering, can obtain the dyeing having high sublimation transfer efficiency, high concentration and high quality, in sublimation transfer dying using inkjet printing, furthermore, excellent in storage stability. SOLUTION: A colorant dispersion comprises (A) a compound expressed by a formula (1), (B) C.I. Disperse Blue 360, and (C) a dispersant, in which when a total content of (A) and (B) is set to 100, a content of (B) is 10 or larger and 90 or smaller, (C) the dispersant contains at least any one selected from the group consisting of polyoxyethylene aryl phenyl ether-based dispersant, and polyoxyethylene arylphenyl ether sulfate-based dispersant. (R1 is H or a nitro group; R2 and R3 may be independently substituted with C1-C4 alkoxy group or C1-C4 alkyl groups that may be substituted with phenyl group; R4 is halogen atom; and R2 and R3 may be mutually coupling to form a ring.) SELECTED DRAWING: None COPYRIGHT: (C)2021,JPOandINPIT
- -
-
Paragraph 0099-0100
(2021/08/13)
-
- SILICON-CONTAINING HETEROCYCLIC COMPOUND, AND QUENCHER
-
Quenchers of the related art do not have a quenching ability high enough to sufficiently inhibit the emission of fluorescence from fluorescence compounds. Therefore, the present invention aims to provide a quencher which can sufficiently quench the fluore
- -
-
Paragraph 0544-0545
(2019/08/22)
-
- Hydrogen-bonding-induced bathochromic effect of Si-coumarin and its use in monitoring adipogenic differentiation
-
Introduction of a heteroatom into a fluorophore was carried out for coumarin through a replacement of its bridging oxygen atom with a silicon atom. The maximum-emission wavelength of Si-coumarin (SiC B) bathochromically shifted from 426 nm in cyclohexane to 626 nm in water. The adipogenic differentiation processes in mesenchymal stem cells were monitored using SiC B.
- Li, Chen,Wang, Ting,Li, Ni,Li, Min,Li, Yuntao,Sun, Yan,Tian, Yang,Zhu, Junru,Wu, Yiqian,Zhang, Dazhi,Cui, Xiaoyan
-
supporting information
p. 11802 - 11805
(2019/10/02)
-
- A class of silicon-substituted coumarin derivatives, and synthesis method thereof
-
The invention discloses a class of silicon-substituted coumarin derivatives, which have a structure represented by a formula I, wherein R is a nitrogen methyl group, a nitrogen ethyl group, a nitrogenhydrogen ethyl group, a nitrogen four-membered ring, a nitrogen ethyl five-membered ring or a nitrogen ethyl six-membered ring. According to the preparation, aniline is subjected to a formylation reaction by using a corresponding aromatic amine as a starting raw material and using phosphorus oxychloride and DMF as reaction reagents; the Ylide reaction of the aldehyde group is performed by using n-butyl lithium as a reaction reagent and using anhydrous THF as a solvent; a lithiation reaction is performed by using n-butyl lithium as reaction reagent to obtain a dimethyl silicon substituted intermediate; and finally diene is subjected to a double decomposition reaction under the catalysis of a Grubbs II catalyst to achieve the intramolecular ring closure, and oxidation is performed with selenium dioxide to obtain the final product. According to the present invention, a class of the novel silicon-substituted coumarin derivatives are synthesized, are sensitive to environmental polarity, and can be used for monitoring the activity of cells in vivo.
- -
-
Paragraph 0037-0039
(2019/10/01)
-
- Development of a Series of Practical Fluorescent Chemical Tools to Measure pH Values in Living Samples
-
In biological systems, the pH in intracellular organelles or tissues is strictly regulated, and differences of pH are deeply related to key biological events such as protein degradation, intracellular trafficking, renal failure, and cancer. Ratiometric fluorescence imaging is useful for determination of precise pH values, but existing fluorescence probes have substantial limitations, such as inappropriate pKa for imaging in the physiological pH range, inadequate photobleaching resistance, and insufficiently long excitation and emission wavelengths. Here we report a versatile scaffold for ratiometric fluorescence pH probes, based on asymmetric rhodamine. To demonstrate its usefulness for biological applications, we employed it to develop two probes. (1) SiRpH5 has suitable pKa and water solubility for imaging in acidic intracellular compartments; by using transferrin tagged with SiRpH5, we achieved time-lapse imaging of pH in endocytic compartments during protein trafficking for the first time. (2) Me-pEPPR is a near-infrared (NIR) probe; by using dextrin tagged with Me-pEPPR, we were able to image extracellular pH of renal tubules and tumors in situ. These chemical tools should be useful for studying the influence of intra- and extracellular pH on biological processes, as well as for in vivo imaging.
- Takahashi, Shodai,Kagami, Yu,Hanaoka, Kenjiro,Terai, Takuya,Komatsu, Toru,Ueno, Tasuku,Uchiyama, Masanobu,Koyama-Honda, Ikuko,Mizushima, Noboru,Taguchi, Tomohiko,Arai, Hiroyuki,Nagano, Tetsuo,Urano, Yasuteru
-
supporting information
p. 5925 - 5933
(2018/05/23)
-
- Dimer-type triarylmethane dye compounds, blue resin composition comprising the same for color filter and color filter using the same
-
The present invention relates to a blue dye compound for a color filter, and more particularly, to a novel dimer-type triarylmethane dye compound having enhanced solubility, high heat resistance, high light resistance and high brightness compared to a conventional dye, and to a blue resin composition for a color filter comprising the same and a color filter using the same. When the dimer type triarylmethane dye compound according to the present invention is used in the blue resin composition for a color filter, a dye compound which has excellent solubility in propylene glycol monomethyl ether acetate (PGMEA) used as a solvent in a process and which has high heat resistance and high brightness can be provided. Therefore, a color filter with high brightness and a high contrast ratio compared to the conventional pigment type color filter can be manufactured through the manufacture of color filters using the same.(AA) Compound 6(BB) Compound 7(CC) Compound 8(DD) Compound 9(EE) Compound 10(FF) Compound 11(GG) Compound 12COPYRIGHT KIPO 2018
- -
-
Paragraph 0058-0062
(2018/05/03)
-
- Synthesis of unsymmetrical Si-rhodamine fluorophores and application to a far-red to near-infrared fluorescence probe for hypoxia
-
Si-Rhodamines are bright fluorophores with red to near-infrared (NIR) emission, and are widely used for fluorescence imaging of biological phenomena. Here, in order to extend the scope of Si-rhodamine fluorophores, we established a versatile synthesis of unsymmetrical Si-rhodamines. To illustrate its value, we used one of these new fluorophores to synthesize a far-red to NIR fluorescence probe for hypoxia, and showed that it can visualize hepatic ischemia in mice in vivo.
- Hanaoka, Kenjiro,Kagami, Yu,Piao, Wen,Myochin, Takuya,Numasawa, Koji,Kuriki, Yugo,Ikeno, Takayuki,Ueno, Tasuku,Komatsu, Toru,Terai, Takuya,Nagano, Tetsuo,Urano, Yasuteru
-
supporting information
p. 6939 - 6942
(2018/06/26)
-
- NEAR-INFRARED FLUORESCENT RATIO TYPE PROBE
-
PROBLEM TO BE SOLVED: To provide a novel near-infrared fluorescent pH probe. SOLUTION: The invention provides a compound represented by general formula (I), or a salt thereof. SELECTED DRAWING: None COPYRIGHT: (C)2018,JPOandINPIT
- -
-
Paragraph 0076; 0077; 0078
(2018/07/31)
-
- A Highly Photostable Near-Infrared Labeling Agent Based on a Phospha-rhodamine for Long-Term and Deep Imaging
-
Various fluorescence microscopy techniques require bright NIR-emitting fluorophores with high chemical and photostability. Now, the significant performance improvement of phosphorus-substituted rhodamine dyes (PORs) upon substitution at the 9-position with a 2,6-dimethoxyphenyl group is reported. The thus obtained dye PREX 710 was used to stain mitochondria in living cells, which allowed long-term and three-color imaging in the vis-NIR range. Moreover, the high fluorescence longevity of PREX 710 allows tracking a dye-labeled biomolecule by single-molecule microscopy under physiological conditions. Deep imaging of blood vessels in mice brain has also been achieved using the bright NIR-emitting PREX 710-dextran conjugate.
- Grzybowski, Marek,Taki, Masayasu,Senda, Kieko,Sato, Yoshikatsu,Ariyoshi, Tetsuro,Okada, Yasushi,Kawakami, Ryosuke,Imamura, Takeshi,Yamaguchi, Shigehiro
-
supporting information
p. 10137 - 10141
(2018/08/06)
-
- Bridge-Caging Strategy in Phosphorus-Substituted Rhodamine for Modular Development of Near-Infrared Fluorescent Probes
-
Replacement of the bridging oxygen atom in rhodamine with phosphorus is one of the most efficient ways for bright near-infrared (NIR) fluorophores with wavelengths over 700 nm. However, the organophosphorus bridge is more versatile than just being a spectrum tuner, it is also a profound solubility booster and photostability enhancer, as proved by a series of phosphorus-substituted rhodamines (PRBs). A unique bridge-caging strategy for efficiently manipulating fluorescence has further been innovated in example PRB2. Consistent with theoretical calculations, the formation of organophosphinate by a caging group as a fluorescence-controller locks the spirolactone into a colorless and nonfluorescent form, whereas decaging, a process induced by a specific stimulus, results in a ring-opened form, which yields strong fluorescence. The bridge-caging strategy is feasible for the modular development of NIR probes. Efficient in vivo imaging of photoillumination, hydrogen peroxide, and enzyme have been achieved on the PRB2 scaffold as a photoactivatable fluorophore, PRB2-hν; fluorescent indicator, PRB2-H2O2; and fluorogenic enzyme substrate, PRB2-NTR, respectively.
- Chai, Xiaoyun,Xiao, Jin,Li, Min,Wang, Chaoming,An, Haiyan,Li, Chen,Li, Yuntao,Zhang, Dazhi,Cui, Xiaoyan,Wang, Ting
-
supporting information
p. 14506 - 14512
(2018/09/11)
-
- PYRAZOLOPYRIMIDINE DERIVATIVES
-
The present invention covers Pyrazolopyrimidine compounds of general formula (I), in which n, o, X, Y, R, Q, R1, R2, R3 and R4 are as defined herein, methods of preparing said compounds, intermediate compounds u
- -
-
Page/Page column 108; 109
(2017/11/10)
-
- Rational design of a fast and selective near-infrared fluorescent probe for targeted monitoring of endogenous nitric oxide
-
The real-time monitoring of nitric oxide (NO) at the subcellular level is still a great challenge. To attain this goal, we developed a fast and selective near-infrared (NIR) fluorescent probe for the targeted tracing of endogenous NO. This probe possesses
- Tang, Junma,Guo, Zhiqian,Zhang, Yutao,Bai, Bing,Zhu, Wei-Hong
-
supporting information
p. 10520 - 10523
(2017/09/29)
-
- Synthesis of meta-substituted monodentate phosphinite ligands and implication in hydroformylation ?
-
Abstract: Synthesis of meta-substituted phosphinite ligands 3,3′-(methoxyphosphanediyl)bis(N,N- diethylaniline) (4a) and methoxybis(3-methoxyphenyl)phosphane (4b), in high yields, has been demonstrated. Typical phosphorus chemical shift between 110–120 ppm, appearance of methoxy protons and corresponding carbon, as well as ESI-MS spectra unambiguously confirmed the existence of phosphinite ligands 4a and 4b. To demonstrate the synthetic usefulness of 4a and 4b, these ligands were tested in the rhodium catalyzed hydroformylation of 1-octene. The diethylamine substituted ligand 4a was found to be highly active, whereas 4b was less reactive but revealed slightly better regioselectivity of 62% under optimized conditions. Additionally, 4a and 4b were found to catalyze the hydroformylation of styrene, 1-undecenol and 1,1-disubstituted functional olefin, methyl methacrylate. Both the ligands displayed excellent conversion of styrene, and 4b revealed an excellent branch selectivity of 75%. Although 1-undecenol proved to be amenable to hydroformylation (85–90% conversion to aldehyde), both the ligands failed to discriminate between the linear and branched products. Substrate methyl methacrylate proved to be highly challenging and reduced conversion (between 33–42%) was observed under optimized conditions. Ligand 4a was found to be highly selective towards linear aldehyde (81% linear selectivity). Graphical Abstract: Synopsis Two step synthetic protocol to access meta-substituted monodentate phosphinite ligands 3,3′-(methoxyphosphanediyl)bis(N,N-diethylaniline) (4a) and methoxybis(3-methoxyphenyl)phosphane (4b) has been developed and the ligands have been fully characterized. Apart from catalyzing the hydroformylation of benchmark substrates 1-octene and styrene, 4a and 4b were found to catalyze the hydroformylation of 1-undecenol, a functional olefin and a highly challenging 1,1-disubstituted functional olefin methyl methacrylate. [Figure not available: see fulltext.].
- Deshmukh, Satej S,Gaikwad, Shahaji R,Pandey, Swechchha,Mali, Pramod S,Chikkali, Samir H
-
p. 1143 - 1152
(2017/08/26)
-
- A specific photosensitizer compound for a target cell.
-
PROBLEM TO BE SOLVED: To provide a photosensitization compound which can apply oxidation stress selectively to a target cell, particularly a reporter enzyme expression cell such as β-galactosidase.SOLUTION: A selective photosensitization compound includes a compound represented by general formula (I) or salt thereof, where A represents a univalent group cut by an enzyme; R, R, R, R, R, and Rrepresent a hydrogen atom, a hydroxyl group or the like; and X represents a C-Calkylene group.
- -
-
Paragraph 0043; 0047
(2017/08/23)
-
- Synthesis of Sterically Protected Xanthene Dyes with Bulky Groups at C-3′ and C-7′
-
Substitution of the xanthene scaffold with bulky groups at C-3′ and C-7′ is expected to protect the electrophilic central methine carbon against nucleophilic attack and inhibit stacking. However, such structures are not readily prepared via traditional xa
- Lei, Zuhai,Li, Xinran,Li, Yi,Luo, Xiao,Zhou, Miaomiao,Yang, Youjun
-
p. 11538 - 11543
(2015/12/01)
-
- One-pot photo-reductive N-alkylation of aniline and nitroarene derivatives with primary alcohols over Au-TiO2
-
We report the photo-catalytic N-alkylation of aniline by Au-TiO 2. We successfully alkylate aniline with several primary alcohols. The combined selectivities of mono- and di-alkylated products were always in excess of 70% and dependent on the alkylating alcohol used. A one-pot reaction from nitrobenzene was found to be possible with several substrates. Preliminary experiments showed that this approach could be adopted for the production of lactams using terminal amino-alcohols. The Royal Society of Chemistry 2013.
- Stibal, David,Sa, Jacinto,Bokhoven, Jeroen A. Van
-
-
- Spirolactonized Si-rhodamine: A novel NIR fluorophore utilized as a platform to construct Si-rhodamine-based probes
-
Spirolactonized Si-rhodamine was prepared as a platform to construct Si-rhodamine-based probes by following the design strategy widely used in rhodamine systems. Among them, the reaction-based probe SiR-Hg was operated for NIR sensing and bioimaging of Hg
- Wang, Ting,Zhao, Qing-Jie,Hu, Hong-Gang,Yu, Shi-Chong,Liu, Xiang,Liu, Li,Wu, Qiu-Ye
-
supporting information; experimental part
p. 8781 - 8783
(2012/10/18)
-
- Novel, side-on, PVK-based nonlinear optical polymers: Synthesis and NLO properties
-
A novel, poly(vinylcarbazole)-based nonlinear optical polymer (side-on type), in which the chromophore was attached to the polymer backbone at the centre of the D-π-A bridge, was synthesized conveniently via the post-Knoevenagel condensation reaction. The structure of chromophore was further modified by the introduction of an isolation spacer (carbazole group) to improve poling efficiency. The ensuing polymer displayed good solubility and high thermal stability and its poled film exhibited a relatively large d33 value of ≤56.0 pm/V.
- Li, Zhong'an,Wang, Li,Xiong, Bi,Ye, Cheng,Qin, Jingui,Li, Zhen
-
experimental part
p. 134 - 139
(2010/10/02)
-
- "H"-shape second order NLO polymers: Synthesis and characterization
-
In this work, two "H"-shape and one "AB"-type second order nonlinear optical (NLO) polymers were prepared for the first time. The linkage positions of chromophores in the "H"-shape polymers were shoulder-to-shoulder, in which the chromophore moieties were
- Li, Zhong'An,Hu, Pan,Yu, Gui,Zhang, Wei,Jiang, Zuoquan,Liu, Yunqi,Ye, Cheng,Qin, Jingui,Li, Zhen
-
experimental part
p. 1220 - 1226
(2010/04/26)
-
- Naphthalene-1,8-diylbis(diphenylmethylium) as an organic two-electron oxidant: Benzidine synthesis via oxidative self-coupling of N,N-dialkylanilines
-
Naphthalene-1,8-diylbis(diphenylmethylium) exhibits a unique electron-transfer reduction behavior due to the close proximity of the two triarylmethyl cations, which form a C-C bond while accepting two electrons, leading to 1,1,2,2-tetraphenylacenaphthene. The preparation of the dication was readily accomplished under anhydrous conditions starting from a cyclic bis(triarylmethyl) ether, derived from 1,8-dibromonaphthalene. The process proceeded via deoxygenation accompanying the formation of a disiloxane on treatment with a silylating agent (Me3SiClO4 or Me 3SiOTf) in 1,1,1,3,3,3-hexafluoropropan-2-ol. The dication was successfully employed for oxidative coupling of N,N-dialkylanilines at the paraposition to afford the corresponding benzidines in good to excellent yield.
- Saitoh, Terunobu,Yoshida, Suguru,Ichikawa, Junji
-
p. 6414 - 6419
(2007/10/03)
-
- 1,8-Bis(diphenylmethylium)naphthalenediyl dication as an organic oxidant: Synthesis of benzidines via self-coupling of N,N-Dialkylanilines
-
(Chemical equation presented) 1,8-Bis(diphenylmethylium)naphthalenediyl dications promoted oxidative coupling of various N,N-dialkylanilines to afford the corresponding para-coupled bisanilines, benzidines, in good to excellent yield. The dications were readily prepared from a cyclic ether precursor, derived from 1,8-dibromonaphthalene, via deoxygenation with a silylating reagent in 1,1,1,3,3,3-hexafluoro-2-propanol under anhydrous conditions.
- Saitoh, Terunobu,Yoshida, Suguru,Ichikawa, Junji
-
p. 4563 - 4565
(2007/10/03)
-