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Chiral Aggregates of Triphenylamine‐Based Dyes for Depleting the Production of Hydrogen Peroxide in the Photochemical Water‐Splitting Process
Author(s) -
Adelizzi Beatrice,
Rösch Andreas T.,
van Rijen Daan J.,
Martire R. Simone,
Esiner Serkan,
Lutz Martin,
Palmans Anja R. A.,
Meijer E. W.
Publication year - 2019
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.201900065
Subject(s) - chemistry , triphenylamine , photosensitizer , supramolecular chemistry , photocurrent , photochemistry , hydrogen peroxide , supramolecular polymers , polymer , conjugated system , combinatorial chemistry , organic chemistry , molecule , materials science , optoelectronics
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.