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Intramolecular Singlet Fission in Pentacene Oligomers via an Intermediate State

Cite this: J. Phys. Chem. B 2023, 127, 20, 4554–4561
Publication Date (Web):May 16, 2023
https://doi.org/10.1021/acs.jpcb.3c00516
Copyright © 2023 American Chemical Society

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    Abstract

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    Intramolecular singlet fission (iSF) is an efficient strategy of multiexciton generation via a singlet exciton splitting into a correlated triplet pair in one organic molecule with more than two chromophores. Propeller-shaped iptycene-linked triisopropylsilyl(TIPS)-ethynyl functionalized pentacene oligomers (pent-monomer, pent-dimer, and pent-trimer) were synthesized, and the iSF dynamics of pent-dimer and -trimer were monitored by a visible–near-IR transient absorption (TA) spectroscopy. Quantum yields of the triplet pair, ∼80%, of both estimated by near-IR TA spectral analysis are in good agreement with the results of global analysis and triplet sensitization experiments. The iSF rate of pent-trimer is slightly faster than that of pent-dimer even with one more chromophore site. The unexpectedly weak difference indicates the existence of an intermediate process to realize iSF. The intermediate process might be determined by through-bond electronic coupling of the homoconjugation bridge in the pentacene oligomers. Our results suggest the importance of the rigid bridge to the fast iSF rate and the elongated lifetime of the correlated triplet pair in pentacene oligomers.

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    The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acs.jpcb.3c00516.

    • Synthetic details and X-ray crystal structure, TA spectra, triplet sensitization experiments, and a table of parameters of iSFs in pentacene oligomers, crystal data of pent-trimer, and NMR spectra of all products in the synthesis (PDF)

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