Chemical engineering of donor-acceptor liquid crystalline dyads and triads for the controlled nanostructuration of organic semiconductors

Yiming Xiao, Xiaolu Su, Lydia Sosa-Vargas, Emmanuelle Lacaze, Benoît Heinrich, Bertrand Donnio, David Kreher, Fabrice Mathevet, André Jean Attias

    Research output: Contribution to journalArticlepeer-review

    22 Citations (Scopus)

    Abstract

    Multi-segregated columnar structures provide a geometrically ideal scheme for ambipolar organic semiconductors, but are not easy to design. A set of novel materials with dyad and triad architectures based on 2 different discotic cores is reported and the conditions of emergence of such complex structures are investigated. The designed molecules associate together electron-donor triphenylene cores (D) and perylene or naphthalene diimides as acceptor moieties (A), both entities being linked via alkyl chain spacers. The evaluation in solution of their HOMO/LUMO energy levels by cyclic voltammetry demonstrates the preservation of the individual features of the D and A units. Their thermal and self-organization behaviors were studied by polarized-light optical microscopy, differential scanning calorimetry, temperature-dependent small-angle X-ray scattering and dilatometry, which permitted detailed investigation of the self-organization behaviour. These D-A compounds turned out to spontaneously self-organize into columnar mesophases at room temperature, with the D and A moieties segregated into either alternated stacks within mixed columns or in distinct columns, the latter providing an ideal configuration for 1D hole and electron transport pathways. In view of potential applications of the triad/dyad template, thin films of these self-organized materials were also probed by atomic force microscopy and grazing incidence X-ray scattering.

    Original languageEnglish
    Pages (from-to)4787-4798
    Number of pages12
    JournalCrystEngComm
    Volume18
    Issue number25
    DOIs
    Publication statusPublished - Jan 1 2016

    All Science Journal Classification (ASJC) codes

    • Chemistry(all)
    • Materials Science(all)
    • Condensed Matter Physics

    Fingerprint Dive into the research topics of 'Chemical engineering of donor-acceptor liquid crystalline dyads and triads for the controlled nanostructuration of organic semiconductors'. Together they form a unique fingerprint.

    Cite this