Nanoribbons or weakly connected acenes? The influence of pyrene insertion on linearly extended ring systems

Qianxiang Ai, Tanner Smith, A. D.Thilanga Liyanage, Samuel M. Mazza, Sean R. Parkin, John E. Anthony, Chad Risko

Research output: Contribution to journalArticlepeer-review

3 Scopus citations


Derived from the lateral fusion of benzene rings, acenes are a class of π-conjugated molecules containing a single aromatic sextet, where system size is inversely correlated with chemical stability. In the pursuit of creating graphene nanoribbons/nanowires, several extended-ring structures have been synthesized through linear combinations of azaacenes and pyrene. Importantly, these extended systems demonstrate enhanced chemical stability and allow for the construction of macromolecular-sized structures. Here, we present a combined quantum-chemical and experimental study to reveal the cost of these improved characteristics in fully carbon-based systems. The results clearly show that pyrene moieties inserted among acene units do not result in long acene-like structures, rather the pyrene-inserted acene is, electronically, a series of (nearly) isolated acenes. The origin of pyrene's electronic blocking effect and implications on oxidized and photoexcited states of these extended-ring systems are detailed. The results of this investigation definitively show that coupling pyrene in an orthogonal orientation (through the 4, 5/9, 10 positions or e/l faces) to acenes should be eschewed if nanographene-/nanowire-like structures are desired.

Original languageEnglish
Pages (from-to)16929-16934
Number of pages6
JournalJournal of Materials Chemistry C
Issue number47
StatePublished - Dec 21 2021

Bibliographical note

Publisher Copyright:
© The Royal Society of Chemistry.

ASJC Scopus subject areas

  • General Chemistry
  • Materials Chemistry


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