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Chemical Structure| 1227040-87-0 Chemical Structure| 1227040-87-0

Structure of 1227040-87-0

Chemical Structure| 1227040-87-0

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Product Citations

Product Citations

Zhumin Zhang ; Jordan L. Chasteen ; Bradley D. Smith ;

Abstract: The chemosensor literature contains many reports of fluorescence sensing using polyaromatic hydrocarbon fluorophores such as pyrene, , or polyaryl(ethynylene), where the fluorophore is excited with ultraviolet light (<400 nm) and emits in the visible region of 400–500 nm. There is a need for general methods that convert these “turn-on” hydrocarbon fluorescent sensors into ratiometric sensing paradigms. One simple strategy is to mix the responsive hydrocarbon sensor with a second non-responsive dye that is excited by ultraviolet light but emits at a distinctly longer wavelength and thus acts as a reference signal. Five new cyanine dye cassettes were created by covalently attaching a pyrene, , or biphenyl(ethynylene) component as the ultraviolet-absorbing energy donor directly to the pentamethine chain of a deep-red cyanine (Cy5) energy acceptor. Fluorescence emission studies showed that these Cy5-cassettes exhibited large pseudo-Stokes shifts and high through-bond energy transfer efficiencies upon excitation with ultraviolet light. Practical potential was demonstrated with two examples of ratiometric fluorescence sensing using a single ultraviolet excitation wavelength. One example mixed a Cy5-cassette with a pyrene-based fluorescent indicator that responded to changes in Cu2+ concentration, and the other example mixed a Cy5-cassette with the fluorescent pH sensing dye, .

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Product Details of [ 1227040-87-0 ]

CAS No. :1227040-87-0
Formula : C26H21BO2
M.W : 376.25
SMILES Code : C(C1C=CC=CC=1)(C1C=CC(=CC=1)B(O)O)=C(C1C=CC=CC=1)C1C=CC=CC=1
MDL No. :MFCD30537204
InChI Key :XSIVQWOJIOHPIZ-UHFFFAOYSA-N
Pubchem ID :68246409

Safety of [ 1227040-87-0 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338

Application In Synthesis of [ 1227040-87-0 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 1227040-87-0 ]

[ 1227040-87-0 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 1227040-87-0 ]
  • [ 4181-20-8 ]
  • C96H69N [ No CAS ]
  • 2
  • [ 1227040-87-0 ]
  • [ 57103-20-5 ]
  • [ 1361123-19-4 ]
  • 3
  • [ 1227040-87-0 ]
  • [ 171408-84-7 ]
  • [ 1601479-56-4 ]
YieldReaction ConditionsOperation in experiment
41% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; water; toluene; for 12h;Reflux; Inert atmosphere; General procedure: A mixture of 2 (0.83 g, 2.2 mmol), 5 (0.48 g, 1 mmol), Pd(PPh3)4 (0.11g, 0.1mmol), and K2CO3 (1.1 g, 8.0 mmol) in toluene/ethanol/water (100 mL, 8/1/1 v/v/v) was heated to reflux for 12 h under nitrogen. Then the reaction mixture was cooled to room temperature and poured into water. The organic layer was extracted with dichloromethane, and the combined organic layers were washed with a saturated brine solution and water, and dried over anhydrous magnesium sulfate. After filtration and solvent evaporation, the residue was purified by silica-gel column chromatography using hexane/dichloromethane as eluent. White solid of (TPE)2PF was obtained in 56percent yield.
  • 4
  • [ 52333-42-3 ]
  • [ 1227040-87-0 ]
  • C33H23N3 [ No CAS ]
  • 5
  • [ 4805-22-5 ]
  • [ 1227040-87-0 ]
  • 5,5'-bis(4-(1,2,2-triphenylethenyl)phenyl)-2,2'-bithiophene [ No CAS ]
YieldReaction ConditionsOperation in experiment
85.5% With tetrakis(triphenylphosphine) palladium(0); caesium carbonate; In tetrahydrofuran; water; for 48h;Reflux; General procedure: A mixture of bromo/dibromo thiophene derivatives (1.00 mmol),Cs2CO3 (814.5 mg, 2.50 mmol), TPE boronic acid (1.20 mmol for Br5Tand 2.20 mmol for 2BrnT, n = 1, 2, 3, 4, 6), catalyst [Pd(PPh3)4] (57.8mg, 0.05 mmol), THF (40 mL) and water (4 mL) was degassed for 15 minand refluxed for 48 h. Then, the mixture was dissolved in H2O (50 mL),extracted with ethyl acetate (3 × 20 mL), dried over anhydrous Na2SO4and concentrated under reduced pressure to afford a residue, purified bya silica gel column with 20 % dichloromethane (DCM) in hexane toafford products.
35% With caesium carbonate; In tetrahydrofuran; water; at 70℃; for 48h;Sealed tube; Use an analytical balance to weigh 5,5'-dibromo-2,2'-dithiophene (32.4mg, 0.1mmol),Tetrastyrene boric acid (82.8mg, 0.22mmol) and cesium carbonate (81.5mg, 0.25mmol)In a 50mL single-neck flask. Add reflux condenser, stir bar and dropping funnel.Measure 1.5 mL water and 13.5 mL tetrahydrofuran to dissolve the reactant. Finally, the catalyst palladium tetraphosphate (12mg, 0.01mmol) was added. Seal, pump air, heat up to 70 degrees Celsius, continue to stir,Condensate and reflux for 48h. Then the mixture was extracted with ethyl acetate,It is dried with anhydrous sodium sulfate, and evaporated in a rotary evaporator to obtain a crude product.Elute with dichloromethane-petroleum ether mixed eluent, silica gel column,The final product-a pale yellow solid (32.2 mg, 35%) was obtained.
 

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