Singlet oxygen generation properties of isometrically dibromated thienyl-containing aza-BODIPYs

Xin-Dong Jiang; Shuang Li; Boris Le Guennic; Denis Jacquemin; Daniel Escudero; Linjiu Xiao

doi:10.1039/c6cp05705e

Singlet oxygen generation properties of isometrically dibromated thienyl-containing aza-BODIPYs

Phys Chem Chem Phys. 2016 Dec 7;18(48):32686-32690. doi: 10.1039/c6cp05705e.

Authors

Xin-Dong Jiang¹, Shuang Li², Boris Le Guennic³, Denis Jacquemin⁴, Daniel Escudero⁵, Linjiu Xiao²

Affiliations

¹ College of Applied Chemistry, Shenyang University of Chemical Technology, Shenyang, 110142, China. xdjiang@syuct.edu.cn and State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian 116024, China.
² College of Applied Chemistry, Shenyang University of Chemical Technology, Shenyang, 110142, China. xdjiang@syuct.edu.cn.
³ Institut des Sciences Chimiques de Rennes, UMR 6226 CNRS, Université de Rennes1, 263 Av. du Général Leclerc, 35042 Cedex Rennes, France. boris.leguennic@univ-rennes1.fr.
⁴ Laboratoire CEISAM, UMR CNRS 6230, Université de Nantes, 2 Rue de la Houssinière, BP92208, 44322 Cedex 3 Nantes, France and Institut Universitaire de France, 1, rue Descartes, 75005 Paris, France.
⁵ Laboratoire CEISAM, UMR CNRS 6230, Université de Nantes, 2 Rue de la Houssinière, BP92208, 44322 Cedex 3 Nantes, France.

PMID: 27711729
DOI: 10.1039/c6cp05705e

Abstract

Isometrically dibromated thienyl-containing aza-BODIPYs CDB-1 and BDB-2 with potential use as photosensitizers (PSs) were successfully prepared and their photophysical properties were fully characterized. Singlet oxygen generation experiments were also performed. In this regard, PS CDB-1 was found to be more effective and had about two-fold rate enhancement compared to PS BDB-2. DFT and TD-DFT calculations helped to provide insights into the distinct intersystem crossing (ISC) processes observed for CDB-1 and BDB-2.