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Chemical Structure| 262861-81-4 Chemical Structure| 262861-81-4

Structure of 262861-81-4

Chemical Structure| 262861-81-4

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Product Citations

Product Citations

Rajapaksha, Ishanka N. ; Wang, Jing ; Leszczynski, Jerzy ; Scott, Colleen N. ;

Abstract: NIR dyes have become popular for many applications, including biosensing and imaging. For this reason, the mol. switch mechanism of the xanthene dyes makes them useful for in vivo detection and imaging of bioanalytes. Our group has been designing NIR xanthene-based dyes by the donor-acceptor-donor approach; however, the equilibrium between their opened and closed forms varies depending on the donors and spacer. We synthesized donor-acceptor-donor NIR xanthene-based dyes with an alkyne spacer via the Sonogashira coupling reaction to investigate the effects of the alkyne spacer and the donors on the maximum absorption wavelength and the mol. switching (ring opening) process of the dyes. We evaluated the strength and nature of the donors and the presence and absence of the alkyne spacer on the properties of the dyes. It was shown that the alkyne spacer extended the conjugation of the dyes, leading to absorption wavelengths of longer values compared with the dyes without the alkyne group. In addition, strong charge transfer donors shifted the absorption wavelength towards the NIR region, while donors with strong π-donation resulted in xanthene dyes with a smaller equilibrium constant DFT/TDDFT calculations corroborated the exptl. data in most of the cases. Dye 2 containing the N,N-dimethylaniline group gave contrary results and is being further investigated.

Keywords: donor-acceptor-donor ; NIR dyes ; xanthene dyes ; amine donors ; alkyne spacers

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Product Details of [ 262861-81-4 ]

CAS No. :262861-81-4
Formula : C20H13N
M.W : 267.32
SMILES Code : C#CC1=CC=C(N2C3=C(C4=C2C=CC=C4)C=CC=C3)C=C1
MDL No. :MFCD12024288
InChI Key :JJIQKIUIIVFHAN-UHFFFAOYSA-N
Pubchem ID :15606338

Safety of [ 262861-81-4 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319
Precautionary Statements:P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313

Application In Synthesis of [ 262861-81-4 ]

* 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 [ 262861-81-4 ]

[ 262861-81-4 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 4181-20-8 ]
  • [ 262861-81-4 ]
  • C58H36IN3 [ No CAS ]
  • 2
  • [ 22034-13-5 ]
  • [ 262861-81-4 ]
  • 4-((4-(9H-carbazol-9-yl)phenyl)ethynyl)benzo[c][1,2,5]thiadiazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diisopropylamine; In tetrahydrofuran; at 20℃; for 6h;Inert atmosphere; To a stirred solution of 4-bromobenzo[c] [1,2,5]thiadiazole(107 mg, 0.50 mmol) and 9-(4-ethynylphenyl)-9H-carbazole(160 mg, 0.60 mmol) in THFe(i-Pr)2NH (30 mL/10 mL),PdCl2(PPh3)2(10 mg) and CuI (5 mg) were added under an argon flow. The reaction mixture was then stirred for 6 h at room temperature and solvent was then evaporated under reduced pressure.The mixture was purified by column chromatography silica gel with CH2Cl2/petroleum (1:2) to obtain the desired compound CEBT as a yellow powder. Yield: 72percent. m.p. > 300 C. FT-IR (KBr, upsilon/cm-1): 3050.2, 2212.2, 1598.8, 1514.9, 1450.0, 1338.9, 1229.6, 838.7, 748.2,722.8. 1H NMR (CDCl3, 400 MHz): 8.16 (d, J 8.0 Hz, 2H), 8.05 (d,J 8.0 Hz, 1H), 7.91 (d, J 8.4 Hz, 2H), 7.87 (d, J 8.0 Hz, 1H), 7.64(d, J 8.4 Hz, 3H), 7.45 (m, 4H), 7.32 (m, 2H); 13C NMR (CDCl3,100 MHz): delta 154.83, 154.77, 140.68, 138.40, 133.67, 132.91, 129.30,127.03, 126.26, 123.80, 122.19, 121.72, 120.55, 120.47, 117.12, 109.89,95.16, 86.13. HRMS (EI mode) (m/z): found (M) 401.0980; calcd for C26H15N3S: 401.0987.
  • 3
  • [ 851786-15-7 ]
  • [ 262861-81-4 ]
  • C80H64N4O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
0.7 g Procedure for 6:A mixture of diimide 5 (1.0 g), 9-(4-ethynylphenyl)carba- zole (1.4 g), triphenylphosphine (0.15 g), Pd(PPh3)2C12 (0.2 g), NEt3 (20 mE) in 80 mE TRF was degassed for 15 mm. Reaction mixture was heated for 5 mm, the Cul (0.03 g) was added; the resulted mixture? was additionally heated for 12 hours. After a mixture reached room temperature, precipitate was filtered out. Filtrate was concentrated to SOmE on a rotor evaporator and poured out into a mixture ethanol-water (1:1), a resulted precipitate was filtered out and then washed with hot ethanol (100 mE). Combination of these two precipitateswas additionally washed with hot ethanol (100 mE) and driedin vacuum at 80C. for 10 hours to produce the product 6 withthe yield of0.7 g.
  • 4
  • [ 1034-49-7 ]
  • [ 110677-45-7 ]
  • [ 262861-81-4 ]
YieldReaction ConditionsOperation in experiment
41% t-BuOK (4 equiv) was allowed to dissolve in dried THF (2 ml/mmol) under argon and the solution was cooled to 78 C. After 20 min, 1.6 equiv of (bromomethyl)triphenylphosphonium bromide was added portionwise and stirring under argon continued for 2 h. Then a solution of aldehyde 8 (2.47 mmol) or 9 (0.74 mmol) in dried THF (2 ml/mmol) was slowly added dropwise and stirring continued for 1 h at 78 C and 20 h at rt. The solution was mixed with the same volume of NH4Cl (aq), acidified with 2 M HCl (aq) and extracted with ethyl acetate (350 ml). The organic layer was dried over Na2SO4, filtered and the solvent was evaporated in vacuo. Purification of the residue by chromatography on a SiO2 column (20% CHCl3 in hexanes) gave the title compound 7a (510 mg), 77%, (yellow solid) or 7b (80 mg, 41%, light-yellow crystalline solid; after chromatography the semi-solid oil was dissolved in hot hexanes, the solution was allowed to reach RT, filtered and concentrated under vacuum).
 

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