Exploring Crystal Structure in Ethyne-Substituted Pentacenes, and Their Elaboration into Crystalline Dehydro[18]annulenes

Matthew J. Bruzek, Emma K. Holland, Anna K. Hailey, Sean R. Parkin, Yueh Lin Loo, John E. Anthony

Research output: Contribution to journalArticlepeer-review


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 dehydro[18]annulene forms. These large, strongly interacting structures did indeed behave as acceptors in polymer photovoltaic devices.

Original languageEnglish
Article numbere1900026
JournalHelvetica Chimica Acta
Issue number4
StatePublished - Apr 2019

Bibliographical note

Funding 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).

Publisher Copyright:
© 2019 Wiley-VHCA AG, Zurich, Switzerland


  • acenes
  • annulenes
  • crystal engineering
  • dehydroannulenes
  • organic photovoltaic
  • pentacenes

ASJC Scopus subject areas

  • Catalysis
  • Biochemistry
  • Drug Discovery
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry


Dive into the research topics of 'Exploring Crystal Structure in Ethyne-Substituted Pentacenes, and Their Elaboration into Crystalline Dehydro[18]annulenes'. Together they form a unique fingerprint.

Cite this