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Cristóbal López J, Del Rio M, Oliden A, et al. Solvent-Sensitive Emitting Urea-Bridged bis-BODIPYs: Ready Access by a One-Pot Tandem Staudinger/Aza-Wittig Ureation. Chemistry. 2017;23(69):17511-17520doi: 10.1002/chem.201703383.
Cristóbal López, J., Del Rio, M., Oliden, A., Bañuelos, J., López-Arbeloa, I., García-Moreno, I., & Gómez, A. M. (2017). Solvent-Sensitive Emitting Urea-Bridged bis-BODIPYs: Ready Access by a One-Pot Tandem Staudinger/Aza-Wittig Ureation. Chemistry (Weinheim an der Bergstrasse, Germany), 23(69), 17511-17520. https://doi.org/10.1002/chem.201703383
Cristóbal López, J, et al. "Solvent-Sensitive Emitting Urea-Bridged bis-BODIPYs: Ready Access by a One-Pot Tandem Staudinger/Aza-Wittig Ureation." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 23,69 (2017): 17511-17520. doi: https://doi.org/10.1002/chem.201703383
Cristóbal López J, Del Rio M, Oliden A, Bañuelos J, López-Arbeloa I, García-Moreno I, Gómez AM. Solvent-Sensitive Emitting Urea-Bridged bis-BODIPYs: Ready Access by a One-Pot Tandem Staudinger/Aza-Wittig Ureation. Chemistry. 2017 Dec 11;23(69):17511-17520. doi: 10.1002/chem.201703383. Epub 2017 Oct 09. PMID: 28853181.
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Chemistry. 2017 Dec 11;23(69):17511-17520. doi: 10.1002/chem.201703383. Epub 2017 Oct 09.

Solvent-Sensitive Emitting Urea-Bridged bis-BODIPYs: Ready Access by a One-Pot Tandem Staudinger/Aza-Wittig Ureation.

Chemistry (Weinheim an der Bergstrasse, Germany)

J Cristóbal López, Mayca Del Rio, Ainhoa Oliden, Jorge Bañuelos, Iñigo López-Arbeloa, Inmaculada García-Moreno, Ana M Gómez

Affiliations

  1. Bio-organic Chemistry Department, Instituto de Química Orgánica General (IQOG-CSIC), Juan de la Cierva 3, 28006, Madrid, Spain.
  2. Departamento Química Física, Universidad del País Vasco-EHU, Aptd. 644, 48080, Bilbao, Spain.
  3. Departamento de Sistemas de baja Dimensionalidad, SuperficiesyMateria Condensada, Instituto de Química Física Rocasolano, CSIC, Serrano 119, 28006, Madrid, Spain.

PMID: 28853181 DOI: 10.1002/chem.201703383

Abstract

Herein we describe the synthesis, and computationally aided photophysical characterization of a new set of urea-bridged bis-BODIPY derivatives. These new dyads are efficiently obtained by a one-pot tandem Staudinger/aza-Wittig ureation protocol, from easily accessible meso-phenyl ortho-azidomethyl BODIPYs. These symmetric bis-BODIPYs outstand by a high absorption probability and excellent fluorescence and laser emission in less polar media. Nevertheless, this emission ability decreases in more polar media, which is ascribed to a light-induced charge-transfer from the urea spacer to the dipyrrin core, a process that can be modulated by appropriate changes in the substitution pattern of the BODIPY core. Furthermore, this ureation protocol can also be employed for the direct conjugation of our BODIPY-azides to amine-containing compounds, thus providing access to fluorescent non-symmetric ureas.

© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Keywords: Staudinger reaction; aza-Wittig; charge transfer; fluorescence; ureation

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