Exploration of Transition Metal Complexes Bearing Naphthalene Diimide (NDI) Based Ligands

Undergraduate #35
Discipline: Chemistry and Chemical Sciences
Subcategory: Materials Science

David Barnes - Hampton University
Co-Author(s): Benjamin R. Reiner, Brandeis University, Waltham, Massachusetts; Casey R. Wade, Brandeis University, Waltham, Massachusetts.

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Rylene diimides are a modular class of molecules with rich photochemistry and electrochemistry. These properties make these molecules good candidates as redox active ligands on transition metals. However, to the best of our knowledge, there has been no investigation in the effect of placing rylene diimides in the primary or secondary coordination sphere of metal cations. Previous work in the lab has focused on using a subclass of rylenes, naphthalene diimides (NDIs). The lab has recently reported a careful investigation of the interactions between reduced NDIs and charge dense alkali and alkali earth metal cations. The lab continues to investigate the interactions between NDIs and redox active cations such as transition metals. Herein, we report the synthesis of a novel naphthalene diimide-based ligand. This derivative forges a metal binding pocket directly with the naphthalene diimide framework in the hopes of facilitating electronic communication between the NDI core and bound metal cation. Moreover, the donicity of the ligand should be easily tuned by the oxidation state of the NDI core. Preliminary results indicate ligand based reductions at modest potentials and strong absorbance in the visible region suggesting use in photocatalytic applications.

Funder Acknowledgement(s): Brandeis NSF MRSEC, DMR-1420382

Faculty Advisor: Casey R. Wade, cwade@brandeis.edu

Role: I was responsible for the synthesis and characterization of the novel naphthalene diimide-based ligand. I also collected cyclic voltammograms from the synthesized ligand for the purpose of verifying its reduction.