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

• Published in: New journal of chemistry Vol. 44; no. 45; pp. 19459 - 19471
• Main Authors: Farfán-Paredes, Mónica, González-Antonio, Oscar, Tahuilan-Anguiano, Diana E., Peón, Jorge, Ariza, Armando, Lacroix, Pascal G., Santillan, Rosa, Farfán, Norberto
• Format: Journal Article
• Language: English
• Published: Royal Society of Chemistry [1987-....] 23.11.2020
• Subjects: Chemical Sciences; Coordination chemistry
• ISSN: 1144-0546; 1369-9261
• DOI: 10.1039/D0NJ02576C

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, 19 F NMR spectra were analyzed and their fluorescence quantum yields in several solvents were measured. Experimental values of 19 F chemical shift difference Δ δ F 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.