Excited-State Dynamics of 5,14- vs 6,13-Bis(trialkylsilylethynyl)-Substituted Pentacenes: Implications for Singlet Fission

Ryan D. Pensack, Geoffrey E. Purdum, Samuel M. Mazza, Christopher Grieco, John B. Asbury, John E. Anthony, Yueh Lin Loo, Gregory D. Scholes

Research output: Contribution to journalArticlepeer-review

9 Scopus citations


Singlet fission is a process in conjugated organic materials that has the potential to considerably improve the performance of devices in many applications, including solar energy conversion. In any application involving singlet fission, efficient triplet harvesting is essential. At present, not much is known about molecular packing arrangements detrimental to singlet fission. In this work, we report a molecular packing arrangement in crystalline films of 5,14-bis(triisopropylsilylethynyl)-substituted pentacene, specifically a local (pairwise) packing arrangement, responsible for complete quenching of triplet pairs generated via singlet fission. We first demonstrate that the energetic condition necessary for singlet fission is satisfied in amorphous films of the 5,14-substituted pentacene derivative. However, while triplet pairs form highly efficiently in the amorphous films, only a modest yield of independent triplets is observed. In crystalline films, triplet pairs also form highly efficiently, although independent triplets are not observed because triplet pairs decay rapidly and are quenched completely. We assign the quenching to a rapid nonadiabatic transition directly to the ground state. Detrimental quenching is observed in crystalline films of two additional 5,14-bis(trialkylsilylethynyl)-substituted pentacenes with either ethyl or isobutyl substituents. Developing a better understanding of the losses identified in this work, and associated molecular packing, may benefit overcoming losses in solids of other singlet fission materials.

Original languageEnglish (US)
Pages (from-to)9784-9793
Number of pages10
JournalJournal of Physical Chemistry C
Issue number23
StatePublished - Jun 16 2022

All Science Journal Classification (ASJC) codes

  • Electronic, Optical and Magnetic Materials
  • General Energy
  • Surfaces, Coatings and Films
  • Physical and Theoretical Chemistry


Dive into the research topics of 'Excited-State Dynamics of 5,14- vs 6,13-Bis(trialkylsilylethynyl)-Substituted Pentacenes: Implications for Singlet Fission'. Together they form a unique fingerprint.

Cite this