As conjugated organic materials combine the electronic and optical properties of classical inorganic semiconductors with many of the desirable properties of common organic plastics, these materials have continued to receive considerable fundamental and technological interest. In addition to their mechanical flexibility and potential low production costs, a significant highlight of these materials is the ability to tune their properties at the molecular level. One such intriguing approach to the synthetic tuning of these materials is the incorporation of transition metal species as potential pathways to the development of new electronic, catalytic, and sensing materials.  Square-planar metal dithiolene complexes are attractive for this tuning as they mimic the planar structural nature of conjugated organic systems and exhibit good electronic delocalization across the metal dithiolene complex. In addition they have been shown to exhibit properties such as superconductivity, nonlinear optical properties, and ferromagnetism. Utilizing new synthetic methods for regioselective functionalization of tribromothiophene, our group has developed a new class of π-extended metal thiophenedithiolenes which are structurally analogous to oligothiophenes while containing a metal thiophenedithiolene unit in the center of the conjugated backbone.  In efforts to tune the properties of these materials, as well as explore the scope of possible materials, both the choice of transition metal (including Ni, Pd, Pt, Au, and Co) and the chemical makeup of the conjugated backbone have been thoroughly studied. The synthesis of these materials, along with their structural, optical, and electrochemical characterization, will be presented. Initial polymerization studies will also be presented in efforts to produce larger conjugated materials.  <br/>

π-Extended metal thiophenedithiolenes: Synthetic approaches to tuning electronic and optical properties

251st National Meeting (2016)

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