0
views
0
recommends
+1 Recommend
0 collections
    0
    shares
      • Record: found
      • Abstract: found
      • Article: found
      Is Open Access

      How To Make Nitroaromatic Compounds Glow: Next‐Generation Large X‐Shaped, Centrosymmetric Diketopyrrolopyrroles

      Read this article at

      Bookmark
          There is no author summary for this article yet. Authors can add summaries to their articles on ScienceOpen to make them more accessible to a non-specialist audience.

          Abstract

          Red‐emissive π‐expanded diketopyrrolopyrroles (DPPs) with fluorescence reaching λ=750 nm can be easily synthesized by a three‐step strategy involving the preparation of diketopyrrolopyrrole followed by N‐arylation and subsequent intramolecular palladium‐catalyzed direct arylation. Comprehensive spectroscopic assays combined with first‐principles calculations corroborated that both N‐arylated and fused DPPs reach a locally excited (S 1) state after excitation, followed by internal conversion to states with solvent and structural relaxation, before eventually undergoing intersystem crossing. Only the structurally relaxed state is fluorescent, with lifetimes in the range of several nanoseconds and tens of picoseconds in nonpolar and polar solvents, respectively. The lifetimes correlate with the fluorescence quantum yields, which range from 6 % to 88 % in nonpolar solvents and from 0.4 % and 3.2 % in polar solvents. A very inefficient (T 1) population is responsible for fluorescence quantum yields as high as 88 % for the fully fused DPP in polar solvents.

          Abstract

          Go with the glow: A two‐step process has been developed that transforms parent diketopyrrolopyrrole into structures with up to 10 fused rings. The absorptions are bathochromically shifted to the deep‐red region and strong red emission is seen, even in nonpolar solvents, despite the presence of NO 2 groups.

          Related collections

          Author and article information

          Contributors
          Denis.Jacquemin@univ-nantes.fr
          dirk.guldi@fau.de
          dtgryko@icho.edu.pl
          Journal
          Angew Chem Int Ed Engl
          Angew Chem Int Ed Engl
          10.1002/(ISSN)1521-3773
          ANIE
          Angewandte Chemie (International Ed. in English)
          John Wiley and Sons Inc. (Hoboken )
          1433-7851
          1521-3773
          10 July 2020
          07 September 2020
          : 59
          : 37 ( doiID: 10.1002/anie.v59.37 )
          : 16104-16113
          Affiliations
          [ 1 ] Institute of Organic Chemistry PAS. 44/52 Kasprzaka 01-224 Warsaw Poland
          [ 2 ] Department of Chemistry and Pharmacy & Interdisciplinary Center for Molecular Materials (ICMM) Friedrich-Alexander-Universität Erlangen-Nürnberg (FAU) Egerlandstrasse 3 91058 Erlangen Germany
          [ 3 ] Department of Chemistry and Pharmacy & Computer-Chemie-Center (CCC) Friedrich-Alexander-Universität Erlangen-Nürnberg Nägelsbachstrasse 25 91052 Erlangen Germany
          [ 4 ] School of Chemistry & Molecular Bioscience, Molecular Horizons University of Wollongong Wollongong NSW 2522 Australia
          [ 5 ] Illawarra Health & Medical Research Institute Wollongong NSW 2522 Australia
          [ 6 ] Université de Nantes CNRS CEISAM UMR 6230 Nantes France
          Author notes
          [†]

          These authors contributed equally to this work.

          Article
          ANIE202005244
          10.1002/anie.202005244
          7689858
          32492240
          © 2020 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA

          This is an open access article under the terms of the http://creativecommons.org/licenses/by/4.0/ License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.

          Page count
          Figures: 12, Tables: 6, References: 99, Pages: 10, Words: 0
          Product
          Funding
          Funded by: Fundacja na rzecz Nauki Polskiej , open-funder-registry 10.13039/501100001870;
          Award ID: TEAM POIR.04.04.00-00-3CF4/16-00
          Award ID: START 98.2016
          Funded by: National Research Foundation of Korea , open-funder-registry 10.13039/501100003725;
          Award ID: 2014K1A1A2064569
          Funded by: Deutsche Forschungsgemeinschaft , open-funder-registry 10.13039/501100001659;
          Award ID: SFB 953
          Funded by: Free State of Bavaria
          Award ID: SolTech
          Categories
          Research Article
          Research Articles
          Donor–Acceptor Systems
          Custom metadata
          2.0
          September 7, 2020
          Converter:WILEY_ML3GV2_TO_JATSPMC version:5.9.4 mode:remove_FC converted:26.11.2020

          Chemistry

          diketopyrrolopyrroles, donor–acceptor systems, dyes/pigments, fluorescence, lactams

          Comments

          Comment on this article