Synthesis, Electrochemistry, and Photophysics of Aza-BODIPY Porphyrin Dyes

Simon Pascal; Léo Bucher; Nicolas Desbois; Christophe Bucher; Chantal Andraud; Claude P Gros

doi:10.1002/chem.201503522

Synthesis, Electrochemistry, and Photophysics of Aza-BODIPY Porphyrin Dyes

Chemistry. 2016 Mar 24;22(14):4971-9. doi: 10.1002/chem.201503522. Epub 2016 Mar 3.

Authors

Simon Pascal¹, Léo Bucher², Nicolas Desbois², Christophe Bucher¹, Chantal Andraud³, Claude P Gros⁴

Affiliations

¹ Univ Lyon, Ecole Normale Supérieure de Lyon, CNRS UMR 5182, Université Lyon 1, Laboratoire de Chimie, 46 allée d'Italie, F69364, Lyon, France.
² Institut de Chimie Moléculaire de l'Université de Bourgogne, ICMUB, UMR 6302, 9 Avenue Alain Savary, BP 47870, 21078, Dijon Cedex, France.
³ Univ Lyon, Ecole Normale Supérieure de Lyon, CNRS UMR 5182, Université Lyon 1, Laboratoire de Chimie, 46 allée d'Italie, F69364, Lyon, France. [email protected].
⁴ Institut de Chimie Moléculaire de l'Université de Bourgogne, ICMUB, UMR 6302, 9 Avenue Alain Savary, BP 47870, 21078, Dijon Cedex, France. [email protected].

PMID: 26938146
DOI: 10.1002/chem.201503522

Abstract

The synthesis of dyad and triad aza-BODIPY-porphyrin systems in two steps starting from an aryl-substituted aza-BODIPY chromophore is described. The properties of the resulting aza-BODIPY-porphyrin conjugates have been extensively investigated by means of electrochemistry, spectroelectrochemistry, and absorption/emission spectroscopy. Fluorescence measurements have revealed a dramatic loss of luminescence intensity, mainly due to competitive energy transfer and photoinduced electron transfer involving charge separation followed by recombination.

Keywords: aza-BODIPYs; electrochemistry; fluorescence spectroscopy; photoinduced electron transfer; polyads; porphyrinoids.

Publication types

Research Support, Non-U.S. Gov't