Synthesis and Characterization of a Nucleobase-Functionalized Dihydropyrrolopyrrole Chromophore
Disciplines
Organic Chemistry | Polymer Chemistry
Abstract (300 words maximum)
Nucleobase-functionalized molecules and polymers have proven to be useful as drug and gene delivery carriers, stimuli-response hydrogels, self-healing materials, and adhesives which motivates their incorporation into conjugated systems. The nucleobase pendant group will serve as an order-inducing motif that will enable molecules or polymers to form multidentate hydrogen bonding, π-stacking, and cation binding interactions. Nucleobase pendants are incorporated as side chain functionalities via a multi-step synthetic strategy. This strategy involved synthesizing nucleobase-functionalized anilines that participate in an Fe-catalyzed multicomponent reaction to attain functionalized pyrrolopyrroles. Nuclear magnetic resonance spectroscopy confirms successful synthesis but also reveals insights into H-bonding motifs between chromophores. The overarching goal of this project is to understand the fundamental structure-property relationships of purine-functionalized molecules that will be important pioneering work for continued development of nucleobase-functionalized molecules and polymers.
Academic department under which the project should be listed
CSM - Chemistry and Biochemistry
Primary Investigator (PI) Name
Graham Collier
Synthesis and Characterization of a Nucleobase-Functionalized Dihydropyrrolopyrrole Chromophore
Nucleobase-functionalized molecules and polymers have proven to be useful as drug and gene delivery carriers, stimuli-response hydrogels, self-healing materials, and adhesives which motivates their incorporation into conjugated systems. The nucleobase pendant group will serve as an order-inducing motif that will enable molecules or polymers to form multidentate hydrogen bonding, π-stacking, and cation binding interactions. Nucleobase pendants are incorporated as side chain functionalities via a multi-step synthetic strategy. This strategy involved synthesizing nucleobase-functionalized anilines that participate in an Fe-catalyzed multicomponent reaction to attain functionalized pyrrolopyrroles. Nuclear magnetic resonance spectroscopy confirms successful synthesis but also reveals insights into H-bonding motifs between chromophores. The overarching goal of this project is to understand the fundamental structure-property relationships of purine-functionalized molecules that will be important pioneering work for continued development of nucleobase-functionalized molecules and polymers.