Research Publication Title

Synthesis of 1,3,5-Tris(p-phenyl acetic acid)benzene Towards the Synthesis of Semi-Elastomeric Polymers to Be Used in Regenerative Medicine

Major

Chemistry

Faculty Mentor

Dr. Ronald Okoth

Keywords

Elastomer, reflux, regenerative medicine, tissue engineering, semi-elastomeric polymer, Grignard reaction, sebacic acid, glycerol, biocompatible

Abstract

This research primarily investigates the production of 1,3,5-Tris(p-phenyl acetic acid)benzene and briefly covers the possibility of its applications in tissue engineering and regenerative medicine. A common problem in tissue engineering and regenerative medicine is found when the engineered and native constructs have elastomeric qualities so different that cell function and tissue development are inhibited. To this end, we synthesized 1,3,5-Tris(p-tolyl)benzene by azeotropic refluxing a mixture of 4-methylacetophenone and triflic acid in toluene for four days. Identification of the product was confirmed by nuclear magnetic resonance spectroscopy. The afforded product was then brominated using N-bromosuccinimide in the presence of azobisisobutyronitrile (AIBN) radical initiator with acetonitrile as the solvent. This reaction yielded 1,3,5-Tris(p-(bromomethyl)phenyl)benzene. The last step in the synthesis of 1,3,5-Tris(p-phenyl acetic acid)benzene will be performed with the well-established Grignard reaction. The final product may then be combined with sebacic acid and glycerol to adjust the rigidity of new semi-elastomeric polymers with the goal of maintaining biocompatibility and increasing elastomeric compatibility with body tissue.

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Synthesis of 1,3,5-Tris(p-phenyl acetic acid)benzene Towards the Synthesis of Semi-Elastomeric Polymers to Be Used in Regenerative Medicine

This research primarily investigates the production of 1,3,5-Tris(p-phenyl acetic acid)benzene and briefly covers the possibility of its applications in tissue engineering and regenerative medicine. A common problem in tissue engineering and regenerative medicine is found when the engineered and native constructs have elastomeric qualities so different that cell function and tissue development are inhibited. To this end, we synthesized 1,3,5-Tris(p-tolyl)benzene by azeotropic refluxing a mixture of 4-methylacetophenone and triflic acid in toluene for four days. Identification of the product was confirmed by nuclear magnetic resonance spectroscopy. The afforded product was then brominated using N-bromosuccinimide in the presence of azobisisobutyronitrile (AIBN) radical initiator with acetonitrile as the solvent. This reaction yielded 1,3,5-Tris(p-(bromomethyl)phenyl)benzene. The last step in the synthesis of 1,3,5-Tris(p-phenyl acetic acid)benzene will be performed with the well-established Grignard reaction. The final product may then be combined with sebacic acid and glycerol to adjust the rigidity of new semi-elastomeric polymers with the goal of maintaining biocompatibility and increasing elastomeric compatibility with body tissue.