46. 2 : 4-Diarylpyrroles. Part IV. The formation of acylated 5-amino-2 : 4-diphenylpyrroles from β-benzoly-α-phenylpropionitrile and some notes on the Leuckart reaction

Davies, W. H.; Rogers, M. A. Thorold

doi:10.1039/jr9440000126

Cited by 20 publications

(10 citation statements)

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“…chalcones and nitromethane, or cyanide, followed by a condensation reaction with ammonium acetate (Scheme 7). One-pot synthetic routes to aza-dipyrrins have been known since 1943, [184][185][186] but it was not until 1994 that aza-BODIPY 17 was reported in the literature and its remarkable spectroscopic properties were highlighted. 187 In recent years, aza-BODIPY dyes have been studied extensively by the O'Shea research group.…”

Section: General Synthetic Methodsmentioning

confidence: 99%

Structural modification strategies for the rational design of red/NIR region BODIPYs

et al. 2014

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This review focuses on classifying different types of long wavelength absorbing BODIPY dyes based on the wide range of structural modification methods that have been adopted, and on tabulating their spectral and photophysical properties. The structure-property relationships are analyzed in depth with reference to molecular modeling calculations, so that the effectiveness of the different structural modification strategies for shifting the main BODIPY spectral bands to longer wavelengths can be readily compared, along with their effects on the fluorescence quantum yield (ΦF) values. This should facilitate the future rational design of red/NIR region BODIPY dyes for a wide range of different applications.

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Section: General Synthetic Methodsmentioning

confidence: 99%

Structural modification strategies for the rational design of red/NIR region BODIPYs

et al. 2014

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“…Likewise, the condensation of nitrosopyrroles leads to aza-dipyrrins, which in turn are complexed with borontrifluoride etherate to the corresponding aza-BODIPY dyes. One-pot synthetic routes towards such deep blue aza-dipyrrins were established as early as 1943, [14][15][16] but the complexation to the aza-BODIPY 21 was not reported until 1994. 17 The one-pot sequence comprises condensation of the nitromethane adducts of chalcones 17 at elevated temperatures with a nitrogen source to form pyrroles 18, which are partially nitrosated to 19 in the reaction mixture (Scheme 4).…”

Section: Synthesis Of the Bodipy Corementioning

confidence: 99%

Fluorescent indicators based on BODIPY

2012

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This critical review covers the advances made using the 4-bora-3a,4a-diaza-s-indacene (BODIPY) scaffold as a fluorophore in the design, synthesis and application of fluorescent indicators for pH, metal ions, anions, biomolecules, reactive oxygen species, reactive nitrogen species, redox potential, chemical reactions and various physical phenomena. The sections of the review describing the criteria for rational design of fluorescent indicators and the mathematical expressions for analyzing spectrophotometric and fluorometric titrations are applicable to all fluorescent probes (206 references).

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“…Dichloromethane was dried/degassed by passing it down an alumina column. 1 H and 13 3-(4-Bromophenyl)-1-(4-methoxyphenyl)prop-2-en-1-one (4b)-43 4-Bromobenzaldehyde (5.00 g, 0.027 mol), 4-methoxyacetophenone (3.22 g, 0.027 mol) and potassium hydroxide (0.108 g, 2.7 mmol) were dissolved in ethanol (30 mL) and stirred at room temperature for 12 h. The product which precipitated upon formation was filtered and washed with ethanol and water. The titled product was obtained as a white solid (7. Bromophenyl)-1-(2,4-dimethoxyphenyl)prop-2-en-1-one (4f)-47,48 A solution of acetophenone (1.95 g, 0.011 mol) in ethanol (11 mL) was added gradually to an aqueous solution of 10% KOH (32 mL) at 0 °C.…”

Section: Experimental Section General Experimental Proceduresmentioning

confidence: 99%

Functionalized BF2 chelated azadipyrromethene dyes

et al. 2008

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Fluorescent molecules that emit in the near infra-red are potentially useful as probes for biotechnology. A relatively under-explored design for probes of this type are the aza-BODIPY dyes; this study was performed to enhance our understanding of these materials and ways in which they may be used in dye cassette systems. Thus, the aza-BODIPY dyes 1a - g were prepared. An advanced intermediate towards an eighth compound in the series, 6h, was made but it could not be complexed with boron effectively to give 1h. Spectroscopic properties of these compounds were recorded, and correlations between substituent effects, UV absorbance, fluorescence emissions, and quantum yields were made. Compound 1a was coupled with a fluorescein-alkyne derivative to give the energy transfer cassettes 2 and 3. Both these compounds gave poor energy transfer, and the possible reasons for this were discussed.

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46. 2 : 4-Diarylpyrroles. Part IV. The formation of acylated 5-amino-2 : 4-diphenylpyrroles from β-benzoly-α-phenylpropionitrile and some notes on the Leuckart reaction

Cited by 20 publications

References 0 publications

Structural modification strategies for the rational design of red/NIR region BODIPYs

Structural modification strategies for the rational design of red/NIR region BODIPYs

Fluorescent indicators based on BODIPY

Functionalized BF2 chelated azadipyrromethene dyes

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