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Highly Soluble Benzo[ghi]perylenetriimide Derivatives: Stable and Air‐Insensitive Electron Acceptors for Artificial Photosynthesis
Author(s) -
Chen HungCheng,
Hsu ChaoPing,
Reek Joost N. H.,
Williams René M.,
Brouwer Albert M.
Publication year - 2015
Publication title -
chemsuschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 2.412
H-Index - 157
eISSN - 1864-564X
pISSN - 1864-5631
DOI - 10.1002/cssc.201500950
Subject(s) - diimide , perylene , chemistry , electron acceptor , photochemistry , acceptor , electron donor , substituent , organic chemistry , molecule , physics , condensed matter physics , catalysis
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 ( E red =−0.11 V vs. the normal hydrogen electrode) that electron‐trapping reactions with O 2 and H 2 O do not occur. The BPTI radical anion on a fluorine‐doped tin oxide|TiO 2 electrode is persistent up to tens of seconds ( t 1/2 =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 C 60 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.