title: Highly Soluble Benzo[ghi]perylenetriimide Derivatives: Stable and Air-Insensitive Electron Acceptors for Artificial Photosynthesis.
abstract: 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.
authors.affiliation: Van 't Hoff Institute for Molecular Sciences, University of Amsterdam, P.O. Box 94157, 1090, GD, Amsterdam, The Netherlands.
authors.forename: Hung-Cheng
authors.initials: HC
authors.lastname: Chen
authors.affiliation: Institute of Chemistry, Academia Sinica, 128 Section 2 Academia Road, Nankang, Taipei, 11529, Taiwan.
authors.forename: Chao-Ping
authors.initials: CP
authors.lastname: Hsu
authors.affiliation: Van 't Hoff Institute for Molecular Sciences, University of Amsterdam, P.O. Box 94157, 1090, GD, Amsterdam, The Netherlands.
authors.forename: Joost N H
authors.initials: JN
authors.lastname: Reek
authors.affiliation: Van 't Hoff Institute for Molecular Sciences, University of Amsterdam, P.O. Box 94157, 1090, GD, Amsterdam, The Netherlands.
authors.forename: René M
authors.initials: RM
authors.lastname: Williams
authors.affiliation: Van 't Hoff Institute for Molecular Sciences, University of Amsterdam, P.O. Box 94157, 1090, GD, Amsterdam, The Netherlands. A.M.Brouwer@uva.nl.
authors.forename: Albert M
authors.identifier: http://orcid.org/0000-0002-1731-3869
authors.initials: AM
authors.lastname: Brouwer
mesh_terms: D004396:Coloring Agents / Q000138:chemical synthesis / Q000737:chemistry; D004563:Electrochemistry; D004579:Electron Transport; D007094:Imides / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010569:Perylene / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D055668:Photochemical Processes; D010788:Photosynthesis; D012995:Solubility
chemical_list: D004396:Coloring Agents; D007094:Imides; D010569:Perylene
keywords: electrochemistry; electron transfer; photosynthesis; pi interactions; water splitting