Isocyanate-, Isothiocyanate-, Urea-, and Thiourea-Substituted Boron Dipyrromethene Dyes as Fluorescent Probes
| Autor: | Laure Bonardi, Pascal Retailleau, Raymond Ziessel, Gilles Ulrich |
|---|---|
| Přispěvatelé: | Institut de Chimie des Substances Naturelles (ICSN), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC) |
| Rok vydání: | 2006 |
| Předmět: |
Models
Molecular MESH: Boron MESH: Isocyanates MESH: Porphobilinogen Porphobilinogen MESH: Molecular Structure Nitro compound Substituent [SDV.BC]Life Sciences [q-bio]/Cellular Biology MESH: Solutions Crystallography X-Ray 010402 general chemistry Photochemistry 01 natural sciences chemistry.chemical_compound Polymer chemistry Electrochemistry Urea Phenyl group Sulfhydryl Compounds MESH: Sulfhydryl Compounds MESH: Urea Boron Fluorescent Dyes chemistry.chemical_classification MESH: Electrochemistry Molecular Structure 010405 organic chemistry Organic Chemistry Temperature MESH: Crystallography X-Ray MESH: Fluorescent Dyes Isocyanate MESH: Temperature 0104 chemical sciences Solutions chemistry Thiourea Functional group Nitro BODIPY MESH: Models Molecular Isocyanates |
| Zdroj: | Journal of Organic Chemistry Journal of Organic Chemistry, American Chemical Society, 2006, 71 (8), pp.3093-102. ⟨10.1021/jo0600151⟩ |
| ISSN: | 1520-6904 0022-3263 |
| Popis: | International audience; Boron dipyrromethene dyes (Bodipy) bearing a meso-phenyl substituent carrying a variety of functional groups can be prepared under mild conditions. A single-crystal X-ray structure determination for the 3,5-dinitrophenyl compound shows the phenyl ring to be almost orthogonal (dihedral angle 84 degrees) to the plane of the Bodipy core, with one nitro group almost coplanar with the ring and the other tilted by approximately 21 degrees. Nitro substituents at the 3-, 4-, and 5- positions of the phenyl group are readily reduced to the corresponding amino groups and then converted to isocyanato, isothiocyanato, urea, thiourea, and some polyimine derivatives, the last providing additional functionality (phenazine and pyridylindole units) suitable for chelation of metal ions. All compounds are redox active, the electron-transfer processes being assigned on the basis of comparisons with model compounds. Their fluorescence properties are sensitive to the phenyl group substituents. The Bodipy unit excited state appears to be a strong reductant (Eo approximately -1.4 V) and a modest oxidant (Eo approximately +1.0 V). Quenching processes in the nitro and phenazine derivatives appear to involve intramolecular photoinduced electron transfer. |
| Databáze: | OpenAIRE |
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