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

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dc.contributor.author Bureš, Filip
dc.contributor.author Cvejn, Daniel
dc.contributor.author Melánová, Klára
dc.contributor.author Beneš, Ludvík
dc.contributor.author Svoboda, Jan
dc.contributor.author Zima, Vítězslav
dc.contributor.author Pytela, Oldřich
dc.contributor.author Mikysek, Tomáš
dc.contributor.author Růžičková, Zdeňka
dc.contributor.author Kityk, I.V.
dc.contributor.author Wojciechowski, Artur
dc.contributor.author AlZayed, Nasser
dc.date.accessioned 2016-03-03T11:00:54Z
dc.date.available 2016-03-03T11:00:54Z
dc.date.issued 2015-12-02
dc.identifier.issn 2050-7526
dc.identifier.uri http://hdl.handle.net/10195/61954
dc.description.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. eng
dc.format p. 468-478 eng
dc.language.iso eng
dc.publisher Royal Society of Chemistry eng
dc.relation.ispartof Journal of Materials Chemistry C, 2016, vol. 4, issue 3 eng
dc.rights open access eng
dc.rights Attribution-NonCommercial 3.0 Czech Republic *
dc.rights.uri http://creativecommons.org/licenses/by-nc/3.0/cz/ *
dc.title Effect of intercalation and chromophore arrangement on the linear and nonlinear optical properties of model aminopyridine push-pull molecules eng
dc.type Article eng
dc.peerreviewed yes eng
dc.publicationstatus published eng
dc.identifier.doi 10.1039/C5TC03499J
dc.relation.publisherversion http://pubs.rsc.org/en/content/articlelanding/2016/tc/c5tc03499j#!divAbstract
dc.identifier.wos WOS:000367985700008
dc.identifier.scopus 2-s2.0-84954124645

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