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The design, synthesis and characterization of five diphenylhydrazone end capped molecules as donors for Bulk Heterojunction (BHJ) solar cells are described. The use of the hydrazone donor instead of the more common amine one is advantageous in terms of synthetic access and overall stability. We show that the variation of both the nature and the substitution pattern of the electron deficient conjugated bridge enables the tuning of the optical energy gap as well as of the HOMO and LUMO. In particular, our data show that the low energy shift of the HOMO level along the series of hydrazone compounds, one of the critical parameters affecting the performance of BHJ cells, is as high as 0.42 eV. We tested all derivatives as donors in a BHJ configuration, using the fullerene derivative [6,6]-phenyl-C71-butyric acid methyl ester (PC71BM) as the acceptor. We found that the trend we observed in the progressive stabilization of the chromophore HOMO level upon increasing the electron accepting capabilities of the conjugated bridge is reflected in the progressive increase of the cell open circuit voltage (Voc). Our preliminary results show that it is possible to obtain a Vocas high as 0.74 V, along with a power conversion efficiency of 1.2%. © 2013 The Royal Society of Chemistry.

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Journal of Materials Chemistry A

Open circuit voltage tuning through molecular design in hydrazone end capped donors for bulk heterojunction solar cells

We report the synthesis, mesomorphic behavior, and mobility values of a series of highly ordered N-substituted triindole-based columnar liquid crystals. Shortening the length of N-alkylic substituents from N-dodecyl to N-methyl chains results in a drastic approach of the disks within the columns and in an impressive increase in charge carrier mobility. An study of aggregation in solution provide insights into the intermolecular forces responsible of the reduction of the intrastack distance as the size of the N-alkyl chains is decreased and offer evidence of stabilization of the columns by the contribution of cooperative CH-π interactions. The materials presented here exhibit mobility values, even in totally misaligned columnar phases, that may compete with those of the best polycrystalline organic semiconductors, without the need of costly vacuum evaporation processes. © 2012 American Chemical Society.

Chemistry of Materials

High hole mobility in triindole-based columnar phases: Removing the bottleneck of homogeneous macroscopic orientation

A new type of intrinsic photoconductor was used as a donor in bulk heterojunction solar cells, in blends with PCBM. The donor is a square planar cyclopalladated coordination complex, with a Nile red moiety and a Schiff base as ligands, coordinated by a Pd(II) metal center. The photoconducting properties of the complex were characterized. Photovoltaic devices exhibit low performance, but the analysis of the wavelength dependence of the efficiency reveals a much higher photocurrent upon absorption of the complex, when compared to the photocurrent obtained via absorption by PCBM. This effect is tied to the higher tendency of the intrinsic photoconductor towards exciton dissociation at the heterojunction. © 2012 Copyright Taylor and Francis Group, LLC.

Molecular Crystals and Liquid Crystals

Enhancement of exciton dissociation efficiency in bulk heterojunction solar cells by using an intrinsic photoconductor component

Two series of polycatenar molecules consisting of a π-conjugated rigid core derived from 3-hexen-1,5-diyne coupled to different types of benzoic acid derivatives have been prepared and their potential as multifunctional materials has been investigated. The size ratio between the rigid core and the benzoate-derived groups, which vary in bulk, is crucial to address self-organization, thus indicating the delicate balance of forces involved in liquid crystalline (LC) behaviour. LC nematic, crystalline or LC columnar behaviour is observed depending on the structure of the benzoate moiety. Hexagonal two-dimensional columnar organization is attained for mesogens with benzoate-derived groups bearing six and nine alkoxylic tails. The stacking unit of the columnar organizations is different depending on the total number of tails, twelve or eighteen, with two molecules and half a molecule per columnar stratum, respectively. Macroscopic properties related to molecular structure, such as luminescence, chirality and electroactivity, have also been studied. Luminescent behaviour is observed for all mesogenic materials, which show higher Stokes shifts than in solution. In addition, supramolecular chirality in the mesophase has been observed for a chiral mesogen. Finally, the photoconducting behaviour of two of the columnar materials has been evaluated. © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2012.

New Journal of Chemistry

A linear conjugated core for functional columnar liquid crystals

The stacking order and distance in columnar phases of triindole-based liquid crystals is controlled by an ethynyl linker (see picture; orange rod) between the central triindole core (green) and the peripheral flexible chains of a discotic mesogen. Hole (h) mobility is very high even if the stacking distances is not very short and the conjugated system is not particularly extended. Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.