Highly Soluble Benzo[ghi]perylenetriimide Derivatives: Stable and Air-Insensitive Electron Acceptors for Artificial Photosynthesis.
A series of new benzo[ghi]perylenetriimide (BPTI) derivatives has been synthesized and characterized. These remarkably soluble BPTI derivatives show strong optical absorption in the range of λ=300-500 nm and have a high triplet-state energy of 1.67 eV. A cyanophenyl substituent renders BPTI such a strong electron acceptor (Ered =-0.11 V vs. the normal hydrogen electrode) that electron-trapping reactions with O2 and H2 O do not occur. The BPTI radical anion on a fluorine-doped tin oxide|TiO2 electrode is persistent up to tens of seconds (t1/2 =39 s) in air-saturated buffer solution. As a result of favorable packing, theoretical electron mobilities (10(-2) ∼10(-1) cm(2) V(-1) s(-1)) are high and similar to the experimental values observed for perylene diimide and C60 derivatives. Our studies show the potential of the cyanophenyl-modified BPTI compounds as electron acceptors in devices for artificial photosynthesis in water splitting that are also very promising nonfullerene electron-transport materials for organic solar cells.
['Chen|Hung-Cheng|HC|', 'Hsu|Chao-Ping|CP|', 'Reek|Joost N H|JN|', 'Williams|René M|RM|', 'Brouwer|Albert M|AM|http://orcid.org/0000-0002-1731-3869']
D004396:Coloring Agents D004563:Electrochemistry D004579:Electron Transport D007094:Imides D015394:Molecular Structure D010569:Perylene D055668:Photochemical Processes D010788:Photosynthesis D012995:Solubility
photosynthesis water splitting electrochemistry electron transfer pi interactions