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 ?=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.

SUBMITTER: Chen HC 

PROVIDER: S-EPMC4648035 | biostudies-literature | 2015 Nov

REPOSITORIES: biostudies-literature