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Hydrogen bonding interfaces in fullerene*TTF ensembles.

Margarita Segura1, Luis Sánchez, Javier de Mendoza

  • 1Departamento de Química Orgánica, Universidad Autónoma de Madrid, Cantoblanco, E-28049, Madrid, Spain.

Journal of the American Chemical Society
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We created stable supramolecular donor-acceptor dyads using C60 and TTF linked by hydrogen bonds. These dyads facilitate through-space electron transfer, offering a new route for artificial photosynthesis.

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Area of Science:

  • Supramolecular Chemistry
  • Materials Science
  • Photochemistry

Background:

  • Supramolecular chemistry enables the design of complex molecular architectures.
  • Donor-acceptor dyads are crucial for electron transfer processes, mimicking natural photosynthesis.

Purpose of the Study:

  • To synthesize novel, thermodynamically stable supramolecular donor-acceptor dyads.
  • To investigate electron transfer mechanisms (through-bond vs. through-space) in these dyads.
  • To explore their potential in artificial photosynthesis.

Main Methods:

  • Synthesis of C60-TTF dyads using guanidinium-carboxylate ion pairs and hydrogen bonding.
  • Molecular architecture tuning via variable spacers (phenyl, biphenyl) and functional groups (ester, amide).
  • Electrochemical studies, steady-state, and time-resolved emission spectroscopy.

Main Results:

  • Successful assembly of stable C60-TTF donor-acceptor dyads.
  • Identification of distinct donor (TTF) and acceptor (C60) characteristics electrochemically.
  • Observation of solvent-dependent fluorescence quenching and formation of radical ion pairs with lifetimes in the nanosecond-to-microsecond range.
  • Evidence for through-space electron transfer due to the dyad's complex network and flexible spacer.

Conclusions:

  • The developed hydrogen-bonded C60-TTF dyads exhibit stable through-space electron transfer.
  • This approach provides a promising strategy for constructing artificial photosynthetic systems.
  • The findings advance the design principles for functional supramolecular assemblies.