Long-lived triplet charge-separated state in naphthalenediimide based donor-acceptor systems

Alexander Aster, Christopher Rumble, Anna Bea Bornhof, Hsin Hua Huang, Naomi Sakai, Tomáš Šolomek, Stefan Matile, Eric Vauthey

Research output: Contribution to journalArticlepeer-review

18 Scopus citations


1,4,5,8-Naphthalenediimides (NDIs) are widely used motifs to design multichromophoric architectures due to their ease of functionalisation, their high oxidative power and the stability of their radical anion. The NDI building block can be incorporated in supramolecular systems by either core or imide functionalization. We report on the charge-transfer dynamics of a series of electron donor-acceptor dyads consisting of a NDI chromophore with one or two donors linked at the axial, imide position. Photo-population of the core-centred π-π* state is followed by ultrafast electron transfer from the electron donor to the NDI. Due to a solvent dependent singlet-triplet equilibrium inherent to the NDI core, both singlet and triplet charge-separated states are populated. We demonstrate that long-lived charge separation in the triplet state can be achieved by controlling the mutual orientation of the donor-acceptor sub-units. By extending this study to a supramolecular NDI-based cage, we also show that the triplet charge-separation yield can be increased by tuning the environment.

Original languageEnglish (US)
Pages (from-to)4908-4915
Number of pages8
JournalChemical Science
Issue number13
StatePublished - Apr 7 2021

All Science Journal Classification (ASJC) codes

  • General Chemistry


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