Controlling Vilsmeier-Haack processes in meso-methylBODIPYs: A new way to modulate finely photophysical properties in boron dipyrromethenes

Palao Utiel, Eduardo; Montalvillo Jiménez, Laura; Esnal Martínez, Ixone; Prieto Montero, Ruth; Rodríguez Agarrabeitia, Antonia; García Moreno, Inmaculada; Bañuelos Prieto, Jorge; López Arbeloa, Íñigo María; Moya Cerero, Santiago De La; Ortiz García, María Josefa

Controlling Vilsmeier-Haack processes in meso-methylBODIPYs: A new way to modulate finely photophysical properties in boron dipyrromethenes

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Official URL

https://doi.org/10.1016/j.dyepig.2017.02.030

Publication date

2017

Publisher

Elsevier

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URI

https://hdl.handle.net/20.500.14352/18156

Citation

Palao Utiel, E., Montalvillo Jiménez, L., Esnal Martínez, I. et al. «Controlling Vilsmeier-Haack Processes in Meso-methylBODIPYs: A New Way to Modulate Finely Photophysical Properties in Boron Dipyrromethenes». Dyes and Pigments, vol. 141, junio de 2017, pp. 286-98. DOI.org (Crossref), https://doi.org/10.1016/j.dyepig.2017.02.030.

Abstract

In the herein work we report the fine and selective control of competitive processes when submitting meso-methylBODIPYs to Vilsmeier-Haack reaction conditions. These competitive processes generate BODIPYs with opposed photophysical properties, from highly fluorescent dyes enabling laser emission, to non-fluorescent singlet-oxygen photosensitizers. The synthetic control is exerted on the basis of the structure of the starting BODIPY, as well as the electrophilic character (hard or soft) of the formylating reagent.