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Issue 1, 2010
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Phase separation and affinity between a fluorinated perylene diimide dye and an alkyl-substituted hexa-peri-hexabenzocoronene

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Abstract

Fluorination of alkyl groups is a known strategy for hindering miscibility, thus promoting phase separation, when blends are prepared with a hydrocarbon compound. A new perylene bis(dicarboximide) derivative functionalized with branched N-perfluoroalkyl moieties (BPF-PDI) has been synthesized as electron acceptor to be potentially used in conjunction with the electron donor hexakis(dodecyl)hexabenzocoronene (HBC-C12) in bulk heterojunction solar cells. Aiming at controlling self-assembly between the two components at the supramolecular level, stoichiometric blends in CHCl3 have been prepared either by spin- or drop-casting onto silicon surfaces, and further subjected to solvent vapour annealing (SVA) treatment in a CHCl3-saturated atmosphere. Spectroscopic investigation in solution shows the formation of supramolecular BPF-PDI–HBC-C12 dimers, with an association constant Kass = (2.1 ± 0.3) × 104 M−1, pointing to a strong and unexpected affinity between the two species within the mixture. Characterization through optical and atomic force microscopies of the deposited samples revealed that the self-assembly behaviour of the blends on SiOx is remarkably different from mono-component films, thus confirming the absence of a macroscopic phase-separation between the two components featuring isolated domains of the neat acceptor or donor compound. In addition, X-ray studies provided evidence for the existence of a local-scale phase separation. These findings are of importance for organic photovoltaics, since they offer a new strategy to control the phase separation at different scales in electron acceptor–donor blends.

Graphical abstract: Phase separation and affinity between a fluorinated perylene diimide dye and an alkyl-substituted hexa-peri-hexabenzocoronene

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Publication details

The article was received on 29 Jul 2009, accepted on 27 Aug 2009 and first published on 24 Sep 2009


Article type: Paper
DOI: 10.1039/B915484A
Citation: J. Mater. Chem., 2010,20, 71-82
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    Phase separation and affinity between a fluorinated perylene diimide dye and an alkyl-substituted hexa-peri-hexabenzocoronene

    G. De Luca, A. Liscio, M. Melucci, T. Schnitzler, W. Pisula, C. G. Clark, L. M. Scolaro, V. Palermo, K. Müllen and P. Samorì, J. Mater. Chem., 2010, 20, 71
    DOI: 10.1039/B915484A

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