Impact of pyrene orientation on the electronic properties and stability of graphene ribbons

Tanner Smith, Karl Thorley, Kevin Dimmitt, Sean Parkin, Oksana Ostroverkhova, John Anthony

Research output: Contribution to journalArticlepeer-review

Abstract

We report the synthesis and study of trialkylsilylethyne-substituted “oblique” pyrene-fused acenes, carbon nanoribbons demonstrating near-IR absorption with reversible oxidation and reduction, and acene-like evolution of electronic properties upon extension of the aromatic core. Their electronic structures are investigated through DFT studies, which support the more delocalized nature of their frontier molecular orbitals compared to more common “vertical” pyrene systems. Despite a longer aromatic core, the more extended of the two examples demonstrates enhanced photostability compared to the shorter derivative, running counter to the trend in linear acenes. The unusual stability of the longer core is ultimately linked to its relatively low T1 energy inhibiting the generation of reactive O2 species. The byproduct generated upon photooxidation of the shorter nanoribbon appears to catalyze the generation of 1O2 due to its large T1 energy, leading to its relatively decreased stability.

Original languageEnglish
Pages (from-to)14816-14822
Number of pages7
JournalJournal of Materials Chemistry C
Volume12
Issue number37
DOIs
StatePublished - Sep 18 2024

Bibliographical note

Publisher Copyright:
© 2024 The Royal Society of Chemistry.

ASJC Scopus subject areas

  • General Chemistry
  • Materials Chemistry

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