- PONy Dyes: Direct Addition of P(III) Nucleophiles to Organic Fluorophores
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Nucleophilic addition of phosphinic acid, phosphites, sodium dialkyl phosphites, phosphoramidites, phosphinites, and phosphonites to highly polarized or cationic fluorophores, followed by oxidation, results in new "PONy" dyes with auxochromic phosphinate, phosphonate, or phosphonamidate groups. The reaction was applied to a wide variety of coumarins, (thio)pyronins, and N-alkylacridinium and 5,6-dihydrobenzo[c]xanthen-12-ium salts as well as a meso-chlorinated BODIPY to provide compact dyes with red-shifted absorption and emission bands and Stokes shifts up to 8200 cm-1.
- Butkevich, Alexey N.,Sednev, Maksim V.,Shojaei, Heydar,Belov, Vladimir N.,Hell, Stefan W.
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- NOVEL DYES WITH PHOSPHINIC ACID, PHOSPHINATE, PHOSPHONATE AND PHOSPHONAMIDATE SUBSTITUENTS AS AUXOCHROMIC GROUPS AND METHODS FOR PREPARING THE SAME
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Compounds of formula I are disclosed: wherein X1, X2, X3, X4 are independently H, F, Cl, Br, I, CN, NO2, OR1, SR1, NR1R2, COR1, COOR1, CONR1R2, PO3R1R2, SO2R1, SO3R1 or R3; R1 and R2 are, e.g., H, alkyl or aryl or optionally a ring; R3 is, e.g., alkyl, alkenyl, alkynyl, aryl or cycloalkyl; Y is OR1, NR1R2, or NR1R3; Q is O, S, SO2, NR, C(R3)2, Si(R3)2, Ge(R3)2, P(═O)R3 or P(═O)OR3; Q and X1 can optionally form part of a ring; L and M are independently OR1, SR1, NR1R2 and R3; L and M can optionally form part of a ring; Z is O, S, NR1, CR1R3 or aryl; and Z and X4 can optionally form part of a ring.
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Paragraph 0260-0262
(2018/08/25)
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- Synthesis of Positional Isomeric Phenylphenalenones
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A series of isomeric phenylphenalenones in which the phenyl ring is located at all possible peripheral positions of the phenalenone nuclei was synthesized. The structural characteristics of the series, in which topological variation is permitted with minimal electronic disturbance, could, in principle, allow for easy pharmacophore recognition when the compounds are aligned in steroidomimetic conformations.
- Ospina, Felipe,Ramirez, Adrian,Cano, Marisol,Hidalgo, William,Schneider, Bernd,Otálvaro, Felipe
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p. 3873 - 3879
(2017/04/11)
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- Triazoliptycenes: A Twist on Iptycene Chemistry for Regioselective Cross-Coupling to Build Nonstacking Fluorophores
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Triazoliptycene fluorophores have been designed and synthesized, in which a three-dimensional propeller-like iptycene motif is employed to suppress intermolecular π-π stacking in the solid state. Key to the success of this modular synthesis is a stereoelectronic bias imposed by the iptycene scaffold, which assists the desired regioselectivity in the C-N cross-coupling step as the last-stage structure diversification from a common precursor.
- Kang, Taewon,Kim, Hongsik,Lee, Dongwhan
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supporting information
p. 6380 - 6383
(2017/12/08)
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- Direct cyanation of picolinamides using K4[Fe(CN)6] as the cyanide source
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The efficient, simple, and environment-friendly route of direct cyanation of picolinamides has been developed with nontoxic K4[Fe(CN)6] as the cyanide source through Pdcatalyzed C-H bond activation. A series of N-(naphthalene-1- yl)picolinamide derivatives were successfully transformed to the corresponding cyanation products. The cyanation mechanism has also been speculated.
- Guan, Dinghui,Han, Lu,Wang, Lulu,Song, He,Chu, Wenyi,Sun, Zhizhong
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p. 743 - 745
(2015/06/22)
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- Design and formation of a large tetrahedral cluster using 1,1′-binaphthyl ligands
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(Chemical Presented) Greater than 700 A3 is the calculated interior volume of a novel [Ga4L6] cluster constructed with a derivatized 1,1′-binaphthyl ligand. Due to the size of the cavity, a guest molecule of suitable size
- Biros, Shannon M.,Yeh, Robert M.,Raymond, Kenneth N.
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supporting information; experimental part
p. 6062 - 6064
(2009/03/11)
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- Synthesis of monofluorinated 1-(naphthalen-1-yl)piperazines
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A series of regioisomerically monofluorinated 1-(naphthalen-1-yl)piperazines is described.
- Repine, Joseph T.,Johnson, Douglas S.,White, Andrew D.,Favor, David A.,Stier, Michael A.,Yip, Judy,Rankin, Trent,Ding, Qizhu,Maiti, Samarendra N.
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p. 5539 - 5541
(2008/02/13)
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- Water Soluble Boronic Acid Fluorescent Reporter Compounds and Methods of Use Thereof
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Described herein are boronic acid fluorescent compounds and methods of use thereof.
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- Naphthalene-based water-soluble fluorescent boronic acid isomers suitable for ratiometric and off-on sensing of saccharides at physiological pH
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Two water-soluble naphthalene-based fluorescent boronic acid isomers, 5-(dimethylamino)naphthalene-1-boronic acid (5-DMANBA, 1) and 4-(dimethylamino)naphthalene-1-boronic acid (4-DMANBA, 2). have been synthesized; their fluorescent properties upon binding with carbohydrates have been determined in aqueous phosphate buffer at pH 7.4. The difference in substitution pattern between 1 and 2 leads to significant differences in their fluorescence properties. For example, addition of fructose (50 mM) to a solution of 1 induced a 61% fluorescence intensity decrease at 513 nm and a 36-fold increase at 433 nm. This revealed that compound 1 is a potential sensor for ratiometric sensing of sugars. The pH titration curves of 1 in the absence and the presence of fructose (50 mM) showed a 93- and 200-fold fluorescence intensity increase at 433 nm, respectively, when pH was increased from 3 to 10. Compound 2, however, does not show ratiometric fluorescent intensity changes, but shows significant fluorescence intensity increase upon addition of a sugar (41-fold intensity increase with 50 mM fructose). The emission intensity of 2 increased by over 170-fold at 445 nm upon changing the pH from 2 to 11. The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2005.
- Gao, Xingming,Zhang, Yanling,Wang, Binghe
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p. 579 - 586
(2007/10/03)
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- 13C NMR investigation of electronic interactions in 5-substituted 1-naphthonitriles
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Carbon-13 NMR chemical shifts of 5-Z-substituted 1-naphthonitriles (1; Z = H, F, Cl, Br, NH2, NMe2, CN, NO2, OMe, CHO, CO2Me) in deuteriochloroform and in neat trifluoroacetic acid (TFA) are reported. The CN carbon shifts are found to correlate well with the dual substituent parameters (DSPs). Negative values of the transmission coefficients in the DSP correlation give evidence of a reverse substituent electronic effect, which is associated with variations in π polarization of the CN multiple bond, due primarily to differences in the through-space field effects of the various Z. The effect diminishes for 1 in neat TFA because of the greater contribution of dipolar ArC+=N- to the resonance hybrid. Deviations of the aromatic carbon shifts from substituent chemical shift additivities are small, yet show distinct patterns for many of the carbon resonances. The deviations of the C-1 - CN ipso carbon shifts of 1 in neutral solvents and in TFA correlate roughly with the DSPs. They are attributable to changes in charge density at C-1 that arise as a consequence of substituent-induced changes in the polarity of the CN bond. The greater than expected shielding that is observed for the C-6 and C-8 resonances accords with reduced electron withdrawal by +R substituents and increased mesomeric activity by electron-donating groups, Z, in response to the CN-induced charge depletion within the adjacent aromatic ring. From the location of data for 5-methoxy-1-naphthonitrile (1; Z = OMe) in the chemical shift correlations of 1 in neat TFA, one can conclude that the methoxy group of this compound, unlike that of 1-methoxynaphthalene itself, is not significantly hydrogen-bonded by TFA.
- Schuster, Ingeborg I.
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p. 301 - 310
(2007/10/03)
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