Effect of iodine substitution pattern on the singlet oxygen generation and solvent depended keto-enol tautomerization behavior of BODIPY photosensitizers. (May 2017)

• Record Type: Journal Article
• Authors: Köksoy, Baybars; Kaya, Esra Nur; Hacıvelioğlu, Ferda; Yeşilot, Serkan; Durmuş, Mahmut
• Is Part Of: Dyes and pigments. Volume 140(2017)
• Page Start: 384
• Page End: 391
• Publication Date: 2017-05
• Subjects: BODIPY -- Iodination -- Fluorescence -- Singlet oxygen -- Photodynamic therapy -- Keto-enol tautomerization; Dyes and dyeing -- Periodicals; Pigments -- Periodicals; 667.2
• DOI: 10.1016/j.dyepig.2017.01.067
• Languages: English
• ISSNs: 0143-7208

Abstract

Abstract: The novel iodinated-BODIPY derivatives (1a and1c) containing one or three iodine atoms were synthesized for the first time. The photochemical and photophysical properties of these BODIPYs were investigated and results were compared with two (1b ) and four (1d ) iodine bearing BODIPY derivatives. Surprisingly, the addition of iodine atoms to the meso-aryl positions of the phenyl moiety caused a color change due to the transformation of the enol form of the aromatic OH group to its keto form depending on the using solvent. This solvent affected keto-enol tautomerization on the BODIPY compounds was determined for the first time. Graphical abstract: The effect of iodine substitution pattern on the singlet oxygen generation were investigated. Surprisingly, the addition of iodine atoms to the meso-aryl positions of the phenyl moiety caused a color change due to the keto-enol tautomerization depend on the using solvent. This solvent affected keto-enol tautomerization on the BODIPY compounds was determined for the first time. Highlights: The BODIPY compounds containing different number of iodine atoms were synthesized. The photochemical and photophysical properties of these BODIPYs were investigated. Solvent depended keto-enol tautomerization on the BODIPY compounds was obtained. Singlet oxygen generation of these BODIPY compounds were determined.