Synthesis of NIR naphthyl-containing aza-BODIPYs and measure of the singlet oxygen generation

Xin-Dong Jiang , Dongmei Xi , Boris Le Guennic (1) , Jin Guan , Denis Jacquemin (2, 3) , Jian Guan , Lin-Jiu Xiao

1 ISCR - Institut des Sciences Chimiques de Rennes
2 IUF - Institut universitaire de France
3 CEISAM - Chimie Et Interdisciplinarité : Synthèse, Analyse, Modélisation

With 1-(6-methoxynaphthalen-2-yl)ethanone as the starting material, aza-BODIPYs bearing naphthyl groups were successfully prepared. Effect of extended π-conjugation by attaching the naphthyl group on photophysical properties was noticeable. The absorption and emission maxima of aza-BODIPY 4 (λabs=706 nm, λem=733 nm) bearing the naphthyl group were bathochromically shifted compared to these of 1 (λabs=688 nm, λem=715 nm) bearing the phenyl group. Moreover, the main computed photophysical data at the best level of calculation, i.e., cLR-PCM(CHCl3)-M06-2X/6-311+G(2d,p)/SOS-CIS(D), were in agreement with the experimental data. Aza-BODIPY 5 as a photosensitizer (λabs=704 nm in toluene) had moderate singlet-oxygen production having about 2.0-fold rate enhancement when compared to that of methylene blue, and it is thought to be a photosensitizer to be potentially used for the singlet oxygen generation

Mots clés: Aza-BODIPY; DFT; Near-infrared; Photosensitizer; Singlet oxygen

Domaines: Chimie

Xin-Dong Jiang, Dongmei Xi, Boris Le Guennic, Jin Guan, Denis Jacquemin, et al.. Synthesis of NIR naphthyl-containing aza-BODIPYs and measure of the singlet oxygen generation. Tetrahedron, 2015, 71 (40), pp.7676--7680. ⟨10.1016/j.tet.2015.07.068⟩. ⟨hal-01208407⟩