Chiral aggregates of triphenylamine-based dyes for depleting the production of hydrogen Peroxide in the photochemical water-splitting process

Beatrice Adelizzi, Andreas T. Rösch, Daan J. van Rijen, R. Simone Martire, Serkan Esiner, Martin Lutz, Anja R.A. Palmans, E.W. Meijer (Corresponding author)

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Abstract

Recent studies on water-splitting photoelectrochemical cells (PECs) have demonstrated the intriguing possibility of controlling the spin state in this chemical reaction to form H 2 and O 2 by exploiting the chirality of organic π-conjugated supramolecular polymers. Although this fascinating phenomenon has been disclosed, the chiral supramolecular materials reported thus far are not optimized for acting as efficient photosensitizer for dye-sensitized PECs. In this work we report on the design, synthesis, and characterization of chiral supramolecular aggregates based on C 3 -symmetric triphenylamine-based dyes that are able to both absorb visible light and control the spin state of the process. Variable temperature-dependent spectroscopic measurements reveal the assembly process of the dyes and confirm the formation of chiral aggregates, both in solution as well as on solid supports. Photoelectrochemical measurements on TiO 2 -based anodes validate the advantage of using chiral supramolecular aggregates as photosensitizer displaying higher photocurrent compared to achiral analogues. Moreover, fluorimetric tests for the quantification of the hydrogen peroxide produced, confirm the possibility of controlling the spin of the reaction exerting spin-selection with chiral supramolecular polymers. These results represent a further step towards the next-generation of organic-based water-splitting solar cells.

Original languageEnglish
Article numbere1900065
Number of pages12
JournalHelvetica Chimica Acta
Volume102
Issue number5
Early online date17 Apr 2019
DOIs
Publication statusPublished - May 2019

Keywords

  • chiral induced spin selectivity
  • chirality
  • dye-sensitized photoelectrochemical cells
  • supramolecular chemistry
  • water splitting

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