Hydantoin-based molecular photoswitches

  1. Martínez-López, D. 1
  2. Yu, M.-L. 3
  3. García-Iriepa, C. 1
  4. Campos, P.J. 1
  5. Frutos, L.M. 2
  6. Golen, J.A. 3
  7. Rasapalli, S. 3
  8. Sampedro, D. 1
  1. 1 Universidad de La Rioja
    info

    Universidad de La Rioja

    Logroño, España

    ROR https://ror.org/0553yr311

  2. 2 Universidad de Alcalá
    info

    Universidad de Alcalá

    Alcalá de Henares, España

    ROR https://ror.org/04pmn0e78

  3. 3 University of Massachusetts Dartmouth
    info

    University of Massachusetts Dartmouth

    New Bedford, Estados Unidos

    ROR https://ror.org/00fzmm222

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Revista:
Journal of Organic Chemistry

ISSN: 0022-3263

Año de publicación: 2015

Volumen: 80

Número: 8

Páginas: 3929-3939

Tipo: Artículo

DOI: 10.1021/ACS.JOC.5B00244 SCOPUS: 2-s2.0-84928139929 WoS: WOS:000353315000022 GOOGLE SCHOLAR

Otras publicaciones en: Journal of Organic Chemistry

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Resumen

A new family of molecular photoswitches based on arylidenehydantoins is described together with their synthesis and photochemical and photophysical studies. A series of hydantoin derivatives have been prepared as single isomers using simple and versatile chemistry in good yields. Our studies show that the photostationary states of these compounds can be easily controlled by means of external factors, such as the light source or filters. Moreover, the detailed investigations proved that these switches are efficient (i.e., they make efficient use of the light energy, are high fatigue resistant, and are very photostable). In some cases, the switches can be completely turned on/off, a desirable feature for specific applications. A series of theoretical calculations have also been carried out to understand the photoisomerization mechanism at the molecular level. © 2015 American Chemical Society.