Water-soluble green perylenediimide (PDI) dyes as potential sensitizers for photodynamic therapy

Yukruk, F
Dogan, AL
Canpinar, H
Guc, D
Akkaya, EU
A series of water-soluble green perylenediimide (PDI) dyes have been synthesized. On red light excitation, these dyes were shown to be efficient generators of singlet oxygen, and in cell culture media, they were shown to display significant light-induced cytotoxic effects on the human erythroleukemia cell line (K-562). It appears that highly versatile PDI dyes are likely to find new applications in photodynamic therapy.


Solid-State Emissive BODIPY Dyes with Bulky Substituents As Spacers
Ozdemir, Tugba; Atilgan, Serdar; Kutuk, Ilker; YILDIRIM, LEYLA; Tulek, Abdullah; BAYINDIR, MEHMET; AKKAYA, Engin Umut (American Chemical Society (ACS), 2009-05-21)
Bright fluorescence of the BODIPY dyes, just like most other fluorophores, is quenched in the solid state due to reabsorption and self-quenching. However, introduction of bulky tert-butyl substituents on the meso-phenyl groups result in more spaced packing in the solid state, resulting in highly luminescent powders and films.
Bis(2-pyridyl)-substituted boratriazaindacene as an NIR-emitting chemosensor for Hg(II)
Coskun, Ali; Yilmaz, M. Deniz; Akkaya, Engin U. (American Chemical Society (ACS), 2007-02-15)
Aryl-substituted boratriazaindacenes (Aza-Bodipy's) are a new class of dyes with long wavelength absorption and emissions. We now report the first application of these dyes in metal ion sensing. 2-Pyridyl substituents at positions 1 and 7 create a well-defined pocket for metal ion binding. The chemosensor described here is selective for Hg(II) ions, and both absorption and emission spectra display large changes that would allow ratiometric sensing.
Phenylethynyl-BODIPY Oligomers: Bright Dyes and Fluorescent Building Blocks
Cakmak, Yusuf; AKKAYA, Engin Umut (American Chemical Society (ACS), 2009-01-01)
Boradiazaindacene dyes were converted Into phenylethynyl-BODIPY oligomers via a cycle of reactions, notably including Sonogashira couplings. As expected, as the number, n, of repeating units Increases, peak absorption and emission wavelengths are shifted to the red end of the visible spectrum, albeit with smaller increments as n Increases, Decyl groups help to keep the solubility remarkably high, and in addition to being very bright red-emitting fluorophores, their rigid rod-like structures could allow thei...
Light harvesting and efficient energy transfer in a boron-dipyrrin (BODIPY) functionalized perylenediimide derivative
Yilmaz, M. Deniz; Bozdemir, O. Altan; Akkaya, Engin U. (American Chemical Society (ACS), 2006-06-22)
Click chemistry has been successfully applied in the synthesis of a bay region tetraboron-dipyrrin (BODIPY) appended perylenediimide (PDI). This light-harvesting molecule presents a large cross section for the absorption of light in the visible region. Excitation energy is efficiently channeled to the perylenediimide core. This novel antenna system is the first demonstration of the efficiency of energy transfer in a BODIPY-PDI bichromophoric system and appears to be highly promising for the design and synth...
Organosilanols as Catalysts in Asymmetric Aryl Transfer Reactions
Özçubukçu, Salih; BOLM, Carsten (American Chemical Society (ACS), 2005-03-01)
Various ferrocene-based organosilanols have been synthesized in four steps starting from achiral ferrocene carboxylic acid. Applying these novel planar-chiral ferrocenes as catalysts in asymmetric phenyl transfer reactions to substituted benzaldehydes afforded products with high enantiomeric excesses. The best result (91% ee) was achieved in the addition to p-chlorobenzaldehyde with organosilanol 2b, which has a tert-butyl substituent on the oxazoline ring and an isopropyl group on the silanol fragment.
Citation Formats
F. Yukruk, A. Dogan, H. Canpinar, D. Guc, and E. Akkaya, “Water-soluble green perylenediimide (PDI) dyes as potential sensitizers for photodynamic therapy,” ORGANIC LETTERS, pp. 2885–2887, 2005, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/67927.