Jump to main content
Jump to site search

Issue 3, 2016
Previous Article Next Article

Effect of intercalation and chromophore arrangement on the linear and nonlinear optical properties of model aminopyridine push–pull molecules

Author affiliations

Abstract

Three push–pull aminopyridine derivatives having D–π–A, D–(π–A)2, and D–(π–A)3 arrangements were examined as model organic chromophores capable of intercalation into inorganic layered materials (alpha modification of zirconium hydrogen phosphate, zirconium 4-sulfophenylphosphonate, and gamma modification of titanium hydrogen phosphate). The fundamental properties of these dyes, their methylated analogues as well as their intercalates were studied by X-ray analysis, electrochemistry, UV/Vis absorption spectra, TGA, IR spectra, SHG, and were completed by DFT calculations. The synthesis of tripodal tris(pyridin-4-yl)amine is given for the first time. The HOMO–LUMO gap, the position of the longest-wavelength absorption maxima, and the dipole moment of aminopyridines can easily be tuned by attaching/removing pyridin-4-yl electron withdrawing units and their quaternization (pyridine vs. pyridinium acceptors). Their intercalation proved to be feasible affording novel inorganic–organic hybrid materials. The intercalation is accompanied by protonation of the guest, which enhances its ICT and strongly anchors the aminopyridines into the confined space of the layered host. Moreover, this process results in ordering of the organic chromophores and also brings improved thermal and chemical robustness. As a result, the measured SHG efficiencies of the intercalates are larger than those observed for the pure organic push–pull chromophores. Hence, the methodology of intercalation turned out to be very useful strategy for property tuning of NLO-active organic molecules.

Graphical abstract: Effect of intercalation and chromophore arrangement on the linear and nonlinear optical properties of model aminopyridine push–pull molecules

Back to tab navigation

Supplementary files

Publication details

The article was received on 26 Oct 2015, accepted on 01 Dec 2015 and first published on 02 Dec 2015


Article type: Paper
DOI: 10.1039/C5TC03499J
Citation: J. Mater. Chem. C, 2016,4, 468-478
  • Open access: Creative Commons BY-NC license
  •   Request permissions

    Effect of intercalation and chromophore arrangement on the linear and nonlinear optical properties of model aminopyridine push–pull molecules

    F. Bureš, D. Cvejn, K. Melánová, L. Beneš, J. Svoboda, V. Zima, O. Pytela, T. Mikysek, Z. Růžičková, I. V. Kityk, A. Wojciechowski and N. AlZayed, J. Mater. Chem. C, 2016, 4, 468
    DOI: 10.1039/C5TC03499J

    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