Small D-π-A Systems with o-Phenylene-Bridged Accepting Units as Active Materials for Organic Photovoltaics

• Published in: Chemistry : a European journal Vol. 19; no. 30; pp. 9948 - 9960
• Main Authors: Leliège, Antoine, Grolleau, Jérémie, Allain, Magali, Blanchard, Philippe, Demeter, Dora, Rousseau, Théodulf, Roncali, Jean
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 22-07-2013; WILEY‐VCH Verlag; Wiley-VCH Verlag
• Subjects: bridging ligands; Chemical Sciences; chromophores; cyclic voltammetry; donor-acceptor systems; solar cells; bridging ligands; chromophores; donor-acceptor systems; solar cells; cyclic voltammetry; polymer; Solar cells; bandgap; donor-acceptor; internal charge-transfer; pi-conjugated; phase-separation; Systems; Cyclic voltammetry; molecular donors; power conversion efficiency; Performance; oligothiophenes; heterojunction solar-cells
• ISSN: 0947-6539; 1521-3765
• DOI: 10.1002/chem.201301054

Donor–acceptor (D–π–A) systems that combine triarylamine donor blocks and dicyanovinyl (DCV) acceptor groups have been synthesized. Starting from the triphenylamine (TPA)thiopheneDCV compound (1) as a reference system, various synthetic approaches have been developed for controlling the light‐harvesting properties and energy levels of the frontier orbitals in this molecule. Thus, the introduction of methoxy groups onto TPA, the replacement of one phenyl ring of TPA by a thiophene ring, or the extension of the π‐conjugating spacer group lead to the modulation of the HOMO level. On the other hand, the fusion of the DCV group onto the vicinal thiophene ring by an ortho‐phenylene bridge allows for a specific fine‐tuning of the LUMO level. The electronic properties of the molecules were analyzed by using UV/Vis spectroscopy and cyclic voltammetry and the compounds were evaluated as donor materials in basic bilayer planar heterojunction solar cells by using C60 as acceptor material. The relationships between the electronic properties of the donors and the performance of the corresponding photovoltaic devices are discussed. Bilayer planar heterojunction solar cells that used reference compound 1 and C70 afforded power‐conversion efficiencies of up to 3.7 %.
Good things in small packages: The bridging of a dicyanovinyl group to the vicinal thiophene by an ortho‐phenylene bridge leads to a new electron‐withdrawing building block, which has been used for the synthesis of small donor–π–acceptor molecular donors with tailored electronic properties. Efficient planar heterojunction solar cells based on these donors of reduced molecular size and C60 or C70 are reported.