New Hindered BODIPY Derivatives: Solution and Amorphous State Fluorescence Properties
| Autor: | Boris A. Trofimov, Rachel Méallet-Renault, Sophie Badré, Cécile Dumas-Verdes, Robert B. Pansu, Jean-Jacques Vachon, Pierre Audebert, Elena Yu. Schmidt, Elena Yu. Senotrusova, Carine Julien, Thanh Truc Vu, Gilles Clavier |
|---|---|
| Přispěvatelé: | Laboratoire de Photophysique et Photochimie Supramoléculaires et Macromoléculaires (PPSM), École normale supérieure - Cachan (ENS Cachan)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), A.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences (SB RAS), BRIO+, ANR-05-PRIB-0028,BRIO+,Ultra Bright BioChips(2005) |
| Rok vydání: | 2009 |
| Předmět: |
chemistry.chemical_classification
fluorescent pigment 010405 organic chemistry Stacking Quantum yield fluorescent solid Chromophore 010402 general chemistry Photochemistry 01 natural sciences Fluorescence 0104 chemical sciences Surfaces Coatings and Films Electronic Optical and Magnetic Materials Amorphous solid [CHIM.THEO]Chemical Sciences/Theoretical and/or physical chemistry chemistry.chemical_compound General Energy chemistry Physical and Theoretical Chemistry Absorption (chemistry) BODIPY Alkyl |
| Zdroj: | Journal of Physical Chemistry C Journal of Physical Chemistry C, American Chemical Society, 2009, 113 (27), pp.11844-11855. ⟨10.1021/jp9019602⟩ |
| ISSN: | 1932-7455 1932-7447 |
| DOI: | 10.1021/jp9019602 |
| Popis: | International audience; Four new hindered boron-dipyrromethene (BODIPY) dyes have been engineered and synthesized by modification of the pyrrole substituents. The chromophores were designed to shift their absorption and emission wavelengths to the red and to show quantitative emission in solid amorphous deposits. [2.2]Paracyclophane (PcP) was grafted on the BODIPY core as well as alkyl chains of various length to force the molecules away one from each other and prevent π-π stacking. The optical spectroscopic and electrochemical properties in solution are presented. Absorption, emission and FLIM were done on drop-casted films of the fluorophores. The addition of alkyl substituents (-Me, -Et, n-Pr) next to the PcP group clearly affects the emission properties in solid state since the dyes display sharper emission bands than in solution and their relative fluorescence quantum yield increases with the number of carbons in the alkyl chain. Fluorescence lifetime images analysis reveals complex decay profiles. Quite a fair description is given by a biexponential fit: the short component is attributed to aggregates and the long component to monomer-like molecules. This population shows a shorter lifetime (2-3.9 ns) compared to solution (6 ns) due to a quenching by aggregates. This quenching is decreasing as the number of carbons on the alkyl side chain is increasing. The combination of a PcP group next to a n-Pr group on a BODIPY is a good combination to get an excellent fluorophore in the solid state. |
| Databáze: | OpenAIRE |
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