Synthesis and Photophysical Characterizations of Pyrroloquinolone Photosensitizers for Singlet Oxygen Production 1

Paul de Bonfils (1) , Catalina Sandoval-Altamirano (2) , Xavier Moreau (3) , Pierrick Nun (1) , Adèle Laurent (1) , German Gunther (2) , Vincent Coeffard (1)

1 CEISAM - Chimie Et Interdisciplinarité : Synthèse, Analyse, Modélisation
2 USACH - Universidad de Santiago de Chile [Santiago]
3 ILV - Institut Lavoisier de Versailles

A series of pyrroloquinolone photosensitizers bearing different halogen substituents (Cl, Br, I) on the heterocyclic framework was studied. These structures were readily prepared through a multi-step synthetic sequence involving an oxidative protocol as an important step to access the quinolone framework. Spectroscopic characterizations and computational investigations were carried out to study the dyes before and after the oxidative step. Interestingly, the fluorescence emission was significantly reduced upon oxidation. In spite of a low photostability under UV light, the pyrroloquinolone photosensitizers proved effective to produce singlet oxygen. Higher singlet oxygen quantum yields were obtained with photosensitizers bearing halogen atoms with a higher atomic number.

Domaines: Chimie organique; Chimie théorique et/ou physique

Paul de Bonfils, Catalina Sandoval-Altamirano, Xavier Moreau, Pierrick Nun, Adèle Laurent, et al.. Synthesis and Photophysical Characterizations of Pyrroloquinolone Photosensitizers for Singlet Oxygen Production 1. Photochemistry and Photobiology, 2022, 99 (2), pp.642-651. ⟨10.1111/php.13681⟩. ⟨hal-03779908⟩