Hydrogen-bonded perylene/terthiophene-materials: synthesis and spectroscopic properties

The synthesis of layered donor/acceptor-materials based on perylenes (1a–c) and ter(thiophen)es (2a, 2b), ordered by hydrogen bonding moieties is reported. Based on the successful (selective) chlorination of 3,4:9,10-perylene tetracarboxylic dianhydride (3) to obtain a perylene derivative with only four chlorine atoms, subsequent functionalization with different hydrogen-bonding moieties is achieved via the azide/alkyne click reaction as proven by extensive ESI-TOF measurements. The perylene- (1a–c) and terthiophene- (2a, 2b) compounds are useful as acceptor and donor parts, respectively, in organic solar cells as proven via UV–vis and fluorescence measurements. Charge transfer between donor and acceptor parts (2a/1b) was determined as 41% via fluorescence resonance energy transfer (FRET), proving the association of the two components via the attached hydrogen bonding moieties. These measurements indicate that the mixture 2a/1b displays large potential for use as a layered ordered material with controlled spacings for organic solar cells based on a thereby facilitated charge-transfer.