Synthesis and characterization of perylene tetracarboxylic propargyl esters as precursor materials for light-harvesting perylene derivatives in organic photonic applications

Sawalha, Mohamad
In this study, two isomerically pure perylene tetracarboxylic propargyl ester derivatives (P4 and P11) were synthesized and characterized to be used as intermediate compounds for bipolar perylene derivatives. The synthesized intermediates are extremely valuable and versatile building blocks, and their optical, photophysical, and electrochemical properties can be further tuned by the attachments of suitable electron-donating groups at the peri or bay positions. Electron-donor azidofluorene was combined with the electron-acceptor perylene tetracarboxylic propargyl ester derivatives (P4 and P11) and new D-A type bipolar molecules (P6 and P12) were obtained. Photophysical, electrochemical, and thermal properties of the synthesized molecules were studied. UV-Vis and emission spectra, fluorescence quantum yield, lifetime, and HOMO-LUMO energy levels were determined and discussed. The synthesized molecules have a great potential to be utilized in organic photonic applications such as dye-sensitized solar cells (DSSCs) and organic light-emitting diodes (OLEDs) owing to their charge transfer and light-harvesting abilities.


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Chiral Baeyer-Villiger (BV) oxidation of cyclic ketones allows rapid access to asymmetric lactones as valuable intermediates in organic chemistry and frequently encountered precursors in enantioselective synthesis. In the first part, BV oxidation of functionalized ketones, especially cyclic -hydroxy and acetoxy ketones is described which could be a straightforward route to the -hydroxy lactones and -hydroxyalkanoic acid derivatives. The -acetoxylation of indanone, tetralone and chromanone derivatives by usi...
Synthesis of chiral acetoxy lactones via the Baeyer-Villiger oxidation of cyclic aromatic acetoxy ketones
Demir, Ayhan Sıtkı; Aybey, Asuman (Elsevier BV, 2008-12-01)
The alpha-acetoxylation of indanones and tetralones by using Mn(OAc)(3) followed by the enzyme catalyzed kinetic resolution of acetoxy ketones furnished both of the enantiomers of alpha-acetoxy ketones in good chemical and optical yields. The Baeyer-Villiger oxidation of alpha-acetoxy ketones with m-CPBA, CF(3)SO(3)H, and CH(2)O(2), at rt gives the corresponding lactones without racemization. The acetoxy ketone moiety migrates selectively in order to form lactones. The mild hydrolysis of lactones affords ph...
Citation Formats
M. Sawalha, “Synthesis and characterization of perylene tetracarboxylic propargyl esters as precursor materials for light-harvesting perylene derivatives in organic photonic applications,” M.S. - Master of Science, Middle East Technical University, 2021.