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 journalArticle

Abstract

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 (US)
Article numbere1900026
JournalHelvetica Chimica Acta
Volume102
Issue number4
DOIs
StatePublished - Apr 2019

All Science Journal Classification (ASJC) codes

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

Keywords

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

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