Synthesis of paracyclophane-peptide based semiconductive peptide hydrogels

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2017
Dolgun, Volkan
Self-assembling peptide hydrogels are becoming an emerging field especially in last decades. Application of these hydrogel forming peptides in biomedical materials, organic electronic devices and tissue engineering is a challenging topic which requires alternative structures to get better and to be easily applied systems. [2.2]Paracyclophane has an interesting structure which two benzene rings are bound to each other with a bridge containing 2 carbons. It is known that the distance between two benzene rings of paracyclophane is shorter, 2.8 - 3.1 Å, than the optimum pi-pi stacking. This provides an easier electron transfer between two rings and makes the compound conductive. On this work, ferrocenoyl phenylalanine (FF) was synthesized and semi-conductive hydrogels were obtained. Electrical properties of these hydrogels such as dielectric constants, conductivities, mobilities and conductivity mechanisms were extensively studied. Organic field-effect transistor which requires low voltage and power was also developed using FF hydrogels. In the second part of the work, three [2.2]paracyclophane mono amino acid and nine dipeptide derivatives were synthesized and characterized by spectroscopic methods. However, it was failed to form hydrogels from these peptide derivatives under various conditions. [2.2]paracyclophane-2-carboxylic was resolved into its enantiomers using chiral amine. Enantiopure [2.2]Paracyclophanoyl phenylalanine was synthesized using each enantiomer of [2.2]paracyclophane-2-carboxylic acid. Hydrogelation studies have not been completed yet. 

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Citation Formats
V. Dolgun, “Synthesis of paracyclophane-peptide based semiconductive peptide hydrogels,” M.S. - Master of Science, Middle East Technical University, 2017.