4.6 Article

Pentacene-Bridge Interactions in an Axially Chiral Binaphthyl Pentacene Dimer

Journal

JOURNAL OF PHYSICAL CHEMISTRY A
Volume 125, Issue 33, Pages 7226-7234

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.jpca.1c05254

Keywords

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Funding

  1. Australian Research Council Centre of Excellence in Exciton Science [CE170100026]
  2. Marie Sklodowska-Curie Individual Fellowship [705113]
  3. Universidad Carlos III de Madrid
  4. European Union's Seventh Framework Programme for research [600371]
  5. el Ministerio de Economia, Industria y Competitividad [COFUND2014-51509]
  6. el Ministerio de Educacion, Cultura y Deporte [CEI-15-17]
  7. Banco Santander and el Ministerio de Ciencia, Innovacion y Universidades [RTI2018-101020-B-I00]
  8. Comunidad de Madrid (Spain)-multiannual agreement with UC3M (Excelencia para el Profesorado Universitario-EPUC3M14)-Fifth regional research plan 2016-2020
  9. National Science Foundation [DMR-2004678]
  10. Department of Defense for a National Defense Science and Engineering Graduate (NDSEG) Fellowship
  11. NSF for GRF [DGE 11-44155]
  12. Marie Curie Actions (MSCA) [705113] Funding Source: Marie Curie Actions (MSCA)

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By designing a compound containing an axially chiral binaphthyl bridge and utilizing its chiroptical response as a marker for intra-molecular singlet fission chromophore-bridge-chromophore interactions, the study demonstrates the promising application of chiroptical techniques in investigating these interactions.
Molecular chirality can be exploited as a sensitive reporter of the nature of intra- and interchromophore interactions in pi-conjugated systems. In this report, we designed an intramolecular singlet fission (iSF)-based pentacene dimer with an axially chiral binaphthyl bridge (2,2'-(2,2'-dimethoxy-[1,1'-binaphthalene]-3,3'-diyl) n-octyl-di-isopropyl silylethynyl dipentacene, BNBP) to utilize its chiroptical response as a marker of iSF chromophore-bridge-chromophore (SFC-beta-SFC) interactions. The axial chirality of the bridge enforces significant one-handed excitonic coupling of the pentacene monomer units; as such, BNBP exhibits significant chiroptical response in the ground and excited states. We analyzed the chiroptical response of BNBP using the exciton coupling method and quadratic response density functional theory calculations to reveal that higher energy singlet transitions in BNBP involve significant delocalization of the electronic density on the bridging binaphthyl group. Our results highlight the promising application of chiroptical techniques to investigate the nature of SFC-beta-SFC interactions that impact singlet fission dynamics.

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