Efficient Synthesis of <i>N</i>,<i>N</i>-Disubstituted 5-Aminothiophene-2-carboxaldehydes by Nucleophilic Aromatic Substitution in Water

Prim, Damien; Kirsch, Gilbert; Nicoud, Jean‐François

doi:10.1055/s-1998-1657

Cited by 34 publications

(25 citation statements)

References 20 publications

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“…Commercially available aldehyde 16 was converted to the piperidine derivative 17 in 97% yield. 27 Knoevenagel condensation of 17 with the various β-cyanoesters 20a–d gave compounds 21a–d in very good yields. 19 Deprotection of the primary amines 21a–d , followed by coupling with the activated coumarin 9 , yielded the final ratiometric dyes 23a–d .…”

Section: Resultsmentioning

confidence: 99%

Synthesis and evaluation of self-calibrating ratiometric viscosity sensors

et al. 2011

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We describe the design, synthesis and fluorescent profile of a family of self-calibrating dyes that provide ratiometric measurements of fluid viscosity. The design is based on covalently linking a primary fluorophore (reference) that displays a viscosity-independent fluorescence emission with a secondary fluorophore (sensor) that exhibits a viscosity-sensitive fluorescence emission. Characterization of fluorescent properties was made with separate excitation of the units and through Resonance Energy Transfer from the reference to the sensor dye. The chemical structures of both fluorophores and the linker length have been evaluated in order to optimize the overall brightness and sensitivity of the viscosity measurements. We also present an application of such ratiometric dyes for the detection of membrane viscosity changes in a liposome model.

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Section: Resultsmentioning

confidence: 99%

Synthesis and evaluation of self-calibrating ratiometric viscosity sensors

et al. 2011

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“…11 The thienyl derivative 2e was prepared following a reported procedure. 22 The aldehyde 3,3-bis(4-(dimethylamino)-phenyl)acrylaldehyde was provided by C. Mayer. 23 UV−Visible Absorption and Emission Studies.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

Linear and Nonlinear Optical Properties of Tris-cyclometalated Phenylpyridine Ir(III) Complexes Incorporating π-Conjugated Substituents

et al. 2013

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The synthesis, luminescence, and nonlinear optical properties of a new series of Ir(ppy)3 (ppy = 2-phenylpyridine) complexes incorporating π-extended vinyl-aryl substituents at the para positions of their pyridine rings are reported. Appropriate substitution of the pyridyl rings allows the tuning of the luminescence properties and the second-order nonlinear optical response of this unusual family of three-dimensional chromophores. Theoretical calculations were performed to evaluate the dipole moments, to gain insight into the electronic structure, and to rationalize the observed optical properties of the investigated complexes.

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“…Knövenagel condensation of 8 27 with β-cyanoester 7 gave compound 9 in good yield as a single stereoisomer (E). 19 Deprotection of the primary amine 9 by treatment with trifluoroacetic acid, followed by coupling with N -succinimidyl-7-methoxycoumarin-3-carboxylate ( 11 ), yielded ratiometric dye 12 in 83% yield.…”

Section: Resultsmentioning

confidence: 99%

Self-calibrating viscosity probes: Design and subcellular localization

Dakanali

Thai

Horn

et al. 2012

Bioorganic & Medicinal Chemistry

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We describe the design, synthesis and fluorescence profiles of new self-calibrating viscosity dyes in which a coumarin (reference fluorophore) has been covalently linked with a molecular rotor (viscosity sensor). Characterization of their fluorescence properties was made with separate excitation of the units and through Resonance Energy Transfer from the reference to the sensor dye. We have modified the linker and the substitution of the rotor in order to change the hydrophilicity of these probes thereby altering their subcellular localization. For instance, hydrophilic dye 12 shows a homogeneous distribution inside the cell and represents a suitable probe for viscosity measurements in the cytoplasm. 2012 Elsevier Ltd. All rights reserved.

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Efficient Synthesis of N,N-Disubstituted 5-Aminothiophene-2-carboxaldehydes by Nucleophilic Aromatic Substitution in Water

Cited by 34 publications

References 20 publications

Synthesis and evaluation of self-calibrating ratiometric viscosity sensors

Synthesis and evaluation of self-calibrating ratiometric viscosity sensors

Linear and Nonlinear Optical Properties of Tris-cyclometalated Phenylpyridine Ir(III) Complexes Incorporating π-Conjugated Substituents

Self-calibrating viscosity probes: Design and subcellular localization

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