1,2,3-Triazole-Diketopyrrolopyrrole Derivatives with Tunable Solubility and Intermolecular Interactions

Angela Punzi, Eliana Maiorano, Francesca Nicoletta, Davide Blasi, Antonio Ardizzone, Nora Ventosa, Imma Ratera, Jaume Veciana, Gianluca Maria Farinola

    Research output: Contribution to journalArticleResearchpeer-review

    22 Citations (Scopus)

    Abstract

    © 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. 1,2,3-Triazole rings bearing hydrophobic aliphatic or hydrophilic oligoether chains were easily introduced at the two ends of the conjugated skeleton of bisthiophene-diketopyrrolopyrrole (TDPP) derivatives by simple click cycloaddition reactions. The combination of side chains with different structures and polarities on the triazole rings with the side chains on the N-atoms of the lactam groups of the TDPP moiety enabled the solubility and the solid-state spectroscopic properties of the resulting conjugated molecules to be tuned. Formation of nanostructured aggregates and dependence of their spectroscopic behavior on the substitution pattern were investigated.
    Original languageEnglish
    Pages (from-to)2617-2627
    JournalEuropean Journal of Organic Chemistry
    Volume2016
    Issue number15
    DOIs
    Publication statusPublished - 1 May 2016

    Keywords

    • Azides
    • Click chemistry
    • Conjugation
    • Dyes/Pigments
    • Nitrogen heterocycles

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