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Issue 1, 2014
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The amide bridge in donor–acceptor systems: delocalization depends on push–pull stress

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Abstract

Transmission of electronic information through amide bonds may be, under appropriate conditions, effectively achieved. In this work, a family of explicitly designed donor–(amide bridge)–acceptor architectures was synthesized. NMR studies and UV-vis absorption solvatochromism support that cross-conjugation leads to measurable polarization across push–pull, amide-bridged molecules. Computational analysis of structural parameters and frontier molecular orbitals shows the contribution of an additional, dienoid amide canonical structure to intramolecular electron delocalization, as the electron donor–acceptor strength of the substituents increases. Within the context of nonlinear optics and molecular materials, computational comparison between amide-bridged molecules and those containing typical linkers shows that there is a compromise between nonlinear optical response, ease of synthesis and chemical inertness, making the systems studied herein interesting alternatives for such applications.

Graphical abstract: The amide bridge in donor–acceptor systems: delocalization depends on push–pull stress

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Publication details

The article was received on 27 Sep 2013, accepted on 17 Oct 2013 and first published on 21 Oct 2013


Article type: Paper
DOI: 10.1039/C3NJ01176C
Citation: New J. Chem., 2014,38, 260-268
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    The amide bridge in donor–acceptor systems: delocalization depends on push–pull stress

    M. Maldonado-Domínguez, R. Arcos-Ramos, M. Romero, B. Flores-Pérez, N. Farfán, R. Santillan, P. G. Lacroix and I. Malfant, New J. Chem., 2014, 38, 260
    DOI: 10.1039/C3NJ01176C

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