The Synthetic Pursuit of meso-tetrakis(arylethynyl)porphyrins
Abstract
The developments of liquid crystalline porphyrins are of interest to chemists in the field of applied chemistry and material science due to their potential as functional organic materials. This pursuit involved synthesizing 5, 10, 15, 20- meso-tetrakis(3,5- or 4-alkoxyphenyl)ethynylporphyrins. Incorporating an ethynyl linker at the meso-positions first involved the preparation of 3-(3,5- or 4-alkoxyphenyl)propynals, then subjecting them to porphyrin syntheses under Lindsey’s conditions. Good overall yields of 3-(4-alkoxyphenyl)propynals were achieved by optimization at each synthetic step: alkylation, Sonogashira cross – coupling reaction combined with desilylation, and formylation. Adjusted Sonogashira reaction conditions and a optimized co-catalyst ratio of 0.05: 0.03 molar equivalence of palladium(0) and copper(I) catalyst respectively, 100% conversion according to 1H NMR spectroscopy was achieved and yields nearing 80% was calculated after desilylation. The successful preparation of 3-(4-alkoxyphenyl)propynals and not 3-(3,5-alkoxyphenyl)propynals with a high yield of 85% was achieved. However, further optimization of meso-tetrakis(4-alkoxyphenyl)ethynylporphyrin reactions involving cobalt carbonyl protected 3-(4-alkoxyphenyl)propynal needs to be accomplished.
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Education--Sciences
Citation
Viccars, J. (2017). The Synthetic Pursuit of meso-tetrakis(arylethynyl)porphyrins (Master's thesis, University of Calgary, Calgary, Canada). Retrieved from https://prism.ucalgary.ca. doi:10.11575/PRISM/28395