Jump to main content
Jump to site search

Issue 2, 2019
Previous Article Next Article

Towards efficient initiators for two-photon induced polymerization: fine tuning of the donor/acceptor properties

Author affiliations

Abstract

In this work we present the design, synthesis and systematic investigation of the optical properties of symmetric triphenylamine (TPA)-substituted thiophenes. The use of electron-donating (–OMe, –tBu, –Me, –TMS), -neutral (–H) or -withdrawing (–F, –CN, –SO2Me) substituents gives rise to D–A–D based two-photon absorption (2PA) chromophores. The photophysical properties of these compounds, including one-photon absorption and 2PA using two-photon-excited fluorescence, were investigated in different organic solvents with varying polarity. The maximum 2PA cross sections prove to be strongly dependent on the nature of the TPA substituent and range between ∼173 GM (Goeppert-Mayer units) and 379 GM. Although most of the investigated substances also exhibit high fluorescence quantum yields, two-photon absorption screening tests of an acrylate monomer formulation revealed the efficiency of these materials as 2PA photoinitiators. These results are supported by quantum chemical calculations of the spin density distribution indicating that the mechanism of polymerization initiation using acrylate monomer is favored by strong localization of the unpaired electrons in the triplet state on the C2 carbon of the thiophene moiety.

Graphical abstract: Towards efficient initiators for two-photon induced polymerization: fine tuning of the donor/acceptor properties

Back to tab navigation

Supplementary files

Publication details

The article was received on 01 Dec 2018, accepted on 08 Feb 2019 and first published on 12 Feb 2019


Article type: Paper
DOI: 10.1039/C8ME00101D
Mol. Syst. Des. Eng., 2019,4, 437-448
  • Open access: Creative Commons BY-NC license
  •   Request permissions

    Towards efficient initiators for two-photon induced polymerization: fine tuning of the donor/acceptor properties

    B. Holzer, M. Lunzer, A. Rosspeintner, G. Licari, M. Tromayer, S. Naumov, D. Lumpi, E. Horkel, C. Hametner, A. Ovsianikov, R. Liska, E. Vauthey and J. Fröhlich, Mol. Syst. Des. Eng., 2019, 4, 437
    DOI: 10.1039/C8ME00101D

    This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence. Material from this article can be used in other publications provided that the correct acknowledgement is given with the reproduced material and it is not used for commercial purposes.

    Reproduced material should be attributed as follows:

    • For reproduction of material from NJC:
      [Original citation] - Published by The Royal Society of Chemistry (RSC) on behalf of the Centre National de la Recherche Scientifique (CNRS) and the RSC.
    • For reproduction of material from PCCP:
      [Original citation] - Published by the PCCP Owner Societies.
    • For reproduction of material from PPS:
      [Original citation] - Published by The Royal Society of Chemistry (RSC) on behalf of the European Society for Photobiology, the European Photochemistry Association, and RSC.
    • For reproduction of material from all other RSC journals:
      [Original citation] - Published by The Royal Society of Chemistry.

    Information about reproducing material from RSC articles with different licences is available on our Permission Requests page.

Search articles by author

Spotlight

Advertisements