Synthesis, Optical Properties, and Regioselective Functionalization of 4a-Aza-10a-boraphenanthrene

  1. Abengózar, A. 1
  2. García-García, P. 1
  3. Sucunza, D. 1
  4. Frutos, L.M. 1
  5. Castano, O. 1
  6. Sampedro, D. 2
  7. Pérez-Redondo, A. 1
  8. Vaquero, J.J. 1
  1. 1 Universidad de Alcalá
    info

    Universidad de Alcalá

    Alcalá de Henares, España

    ROR https://ror.org/04pmn0e78

  2. 2 Universidad de La Rioja
    info

    Universidad de La Rioja

    Logroño, España

    ROR https://ror.org/0553yr311

Revista:
Organic Letters

ISSN: 1523-7060

Año de publicación: 2017

Volumen: 19

Número: 13

Páginas: 3458-3461

Tipo: Artículo

DOI: 10.1021/ACS.ORGLETT.7B01435 SCOPUS: 2-s2.0-85022225602 WoS: WOS:000405358300032 GOOGLE SCHOLAR

Otras publicaciones en: Organic Letters

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Resumen

4a-Aza-10a-boraphenanthrene has been synthesized in only four steps from commercially available materials with a remarkable overall yield of 62%. In contrast to other BN-isosteres of phenathrene, this isomer is weakly fluorescent, which has been explained by means of computational studies that found a low energy conical intersection for the nonradiative deactivation of the excited state. Moreover, a completely regioselective functionalization of 4a-aza-10a-boraphenanthrene at C-1 by reaction with activated electrophiles has been achieved. © 2017 American Chemical Society.