Electroactive Carbon-Centered Anion and Radical Polymers

Timothy M. Swger, Massachusetts Institute of Technology, DMR 1005810

We report electroactive conjugated materials containing a carbon-centered radical based on the 1,3-bisdiphenylene-2-phenylallyl (BDPA) radical that can be reversibly reduced to a delocalized carbanion. Our synthesis of these materials is based on a new anionic polymerization that produces a soluble carbanionic polymer. The ability the dimer (2a) and polymer (3a) to be electrochemicaly cycled between neutral and anionic states is critical to several applications, including battery anodes, in which polycarbanions with lithium counterions are used for charge storage. Additionally, n-dopable (electron-conducting) organic conjugated materials that become conductive upon reduction are essential elements of photovoltaic and field effect transistor devices. Conjugated polymer semiconductors that are p-dopable are abundant, but there remains a limited number of stable n-dopable materials.

2Na+

2a

3a

K+

n

O N(n-Bu)2

For the last three summers (2008, 2009, 2010), I have been the organizer or co-organizer of a Future Faculty Workshop that assists underrepresented minority and/or disadvantaged graduate students and postdoctorates to pursue an academic career. These workshops have, by design, targeted researchers with interests that align with myself and the other organizers (Professors Richard McCullough of Carnegie Mellon University, and Gregory Tew of University of Massachusetts). The goal is that we assist these students with their specific technical development and research vision. The introductions to established professors and peers helps to also establish networking opportunities in their chosen area of research. This workshop has been very successful and a 4th workshop will be held at MIT in July of 2011.

Electroactive Carbon-Centered Anion and Radical Oligomers

Timothy M. Swger, Massachusetts Institute of Technology, DMR 1005810

Group photo of the 2009 Future Facutly Workshop held at Carnegie Mellon University