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Bis(4-nitroanilines) in interactions through a π-conjugated bridge: conformational effects and potential molecular switches

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Abstract

Two molecules, 2,2′-(1,4-phenylenebis(ethyne-2,1-diyl))bis(4-nitroaniline) (PNA) and 2,2′-(1,4-phenylene-bis(ethyne-2,1-diyl))bis(N,N-diethyl-4-nitroaniline) (PDNA), built up from two p-nitroaniline “push–pull” nonlinear optical (NLO) chromophores slightly conjugated through a 1,4-phenylenebis(ethyne-2,1-diyl) bridge have been synthesized and fully characterized. The crystal structure of PNA reveals that the ground (off) state conformation corresponds to the centrosymmetric anti-conformer in which the molecular hyperpolarizability (β) is equal to zero. A computational investigation reveals that, once submitted to an intense electric field (E), the two p-nitroaniline subunits are gradually aligned in the direction of the field with the appearance of a metastable (on) state (β ≠ 0, when E = 0), stabilized by conjugation. A loop of hysteresis is observed during the on [leftrightharpoons] off cycles leading to a form of molecular bistability. The NLO response of PNA has been investigated at different field intensities by the electric-field induced second-harmonic (EFISH) technique to provide experimental evidence for this behavior.

Graphical abstract: Bis(4-nitroanilines) in interactions through a π-conjugated bridge: conformational effects and potential molecular switches

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Publication details

The article was received on 19 Jul 2017, accepted on 04 Sep 2017 and first published on 05 Sep 2017


Article type: Paper
DOI: 10.1039/C7NJ02622F
Citation: New J. Chem., 2017, Advance Article
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    Bis(4-nitroanilines) in interactions through a π-conjugated bridge: conformational effects and potential molecular switches

    T. Guerrero, R. Santillan, H. García-Ortega, O. G. Morales-Saavedra, N. Farfán and P. G. Lacroix, New J. Chem., 2017, Advance Article , DOI: 10.1039/C7NJ02622F

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