Bis(4-nitroanilines) in interactions through a π-conjugated bridge: Conformational effects and potential molecular switches
New Journal of Chemistry, ISSN: 1369-9261, Vol: 41, Issue: 20, Page: 11881-11890
2017
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Article Description
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 -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.
Bibliographic Details
http://www.scopus.com/inward/record.url?partnerID=HzOxMe3b&scp=85030992354&origin=inward; http://dx.doi.org/10.1039/c7nj02622f; http://xlink.rsc.org/?DOI=C7NJ02622F; http://pubs.rsc.org/en/content/articlepdf/2017/NJ/C7NJ02622F; https://xlink.rsc.org/?DOI=C7NJ02622F; https://dx.doi.org/10.1039/c7nj02622f; https://pubs.rsc.org/en/content/articlelanding/2017/nj/c7nj02622f
Royal Society of Chemistry (RSC)
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