Computational study on fluoride recognition by an urea-activated phthalimide chemosensor

  1. Pérez-Ruiz, R. 2
  2. Griesbeck, A.G. 3
  3. Sampedro, D. 1
  1. 1 Universidad de La Rioja
    info

    Universidad de La Rioja

    Logroño, España

    ROR https://ror.org/0553yr311

  2. 2 Universidad Politécnica de Valencia
    info

    Universidad Politécnica de Valencia

    Valencia, España

    ROR https://ror.org/01460j859

  3. 3 University of Cologne
    info

    University of Cologne

    Colonia, Alemania

    ROR https://ror.org/00rcxh774

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Revista:
Tetrahedron

ISSN: 0040-4020

Any de publicació: 2012

Volum: 68

Número: 29

Pàgines: 5724-5729

Tipus: Article

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DOI: 10.1016/J.TET.2012.05.043 SCOPUS: 2-s2.0-84862009056 WoS: WOS:000305855800003 GOOGLE SCHOLAR

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Resum

The mechanism of the fluoride anion recognition by an urea-phthalimide chemosensor has been studied in detail by means of CASPT2//CASSCF calculations. Computational data are in well-agreement with changes in the photophysical properties previously reported experimentally in the presence or absence of fluoride anion. In both cases, fast relaxation from the S 2 potential energy surface leads to S 1 population. Deactivation of the excited state is in agreement with the experimental change in fluorescence observed when the anion is present. Mechanistic information obtained allows to provide an explanation of the experimental data and to suggest some modifications to improve the synthetic applicability of this type of chemosensors. © 2012 Elsevier Ltd. All rights reserved.