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Article Dans Une Revue New Journal of Chemistry Année : 2020

Physicochemical and computational insight of 19 F NMR and emission properties of meso -( o -aryl)-BODIPYs

Résumé

A series of electronic and physicochemical parameters were explored to determine their effect on experimental spectroscopic and photophysical data. Through a systematic obtention of a series of meso-(o-aryl)-BODIPYs, 19F NMR spectra were analyzed and their fluorescence quantum yields in several solvents were measured. Experimental values of 19F chemical shift difference ΔδF correlate well with σ-Hammett constants, which is indicative of the inductive nature of the functional groups on the fluorine atoms. A computational DFT exploration of rotational energy barriers, electrostatic potential maps, group electronegativity, charge partitions and hardness/softness provided insight into how those traits can be directly related to the measured features. Expanded understanding of such characteristics provides design arguments and a structure–property relationship, which in a more advantageous way, would help to understand the properties of the synthesized molecules and of future attempts that are structurally related.
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Dates et versions

hal-03150783 , version 1 (24-02-2021)

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Mónica Farfán-Paredes, Oscar González-Antonio, Diana E Tahuilan-Anguiano, Jorge Peón, Armando Ariza, et al.. Physicochemical and computational insight of 19 F NMR and emission properties of meso -( o -aryl)-BODIPYs. New Journal of Chemistry, 2020, 44 (45), pp.19459-19471. ⟨10.1039/D0NJ02576C⟩. ⟨hal-03150783⟩
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