Approaches to control the self-assembly of aromatic structures to enhance intermolecular electronic coupling are the key to the development of new electronic and photonic materials. Acenes in particular have proven simple to functionalize to induce strong π-stacking interactions, although finer control of intermolecular π-overlap has proven more difficult to accomplish. In this report, we describe how very weak hydrogen bonding interactions can exert profound impact on solid-state order in solubilized pentacenes, inducing self-assembly in either head-to-tail motifs with strong 2-D π-stacking, or head-to-head orientations with much weaker, 1-D π-stacking arrangements. In order to achieve 3-D π-stacking useful for photovoltaic applications, we elaborated a series of diethynyl pentacenes to their trimeric dehydroannulene forms. These large, strongly interacting structures did indeed behave as acceptors in polymer photovoltaic devices.
|Journal||Helvetica Chimica Acta|
|State||Published - Apr 2019|
Bibliographical noteFunding Information:
J. E. A., S. R. P., and E. K. H. thank the U.S. National Science Foundation for support of the synthesis of novel aromatic materials (CHE-1609974) and for diffractometer support funding (MRI: CHE-0319176, CHE-1625732).
© 2019 Wiley-VHCA AG, Zurich, Switzerland
- crystal engineering
- organic photovoltaic
ASJC Scopus subject areas
- Drug Discovery
- Physical and Theoretical Chemistry
- Organic Chemistry
- Inorganic Chemistry