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Sola-Llano R, Jiménez J, Avellanal-Zaballa E, et al. BOPHYs . Dyes Pigm. 2019;170doi: 10.1016/j.dyepig.2019.107662.
Sola-Llano, R., Jiménez, J., Avellanal-Zaballa, E., Johnson, M., Cabreros, T. A., Moreno, F., Maroto, B. L., Muller, G., Bañuelos, J., Cerdán, L., García-Moreno, I., & de la Moya, S. (2019). BOPHYs . Dyes and pigments : an international journal, 170. https://doi.org/10.1016/j.dyepig.2019.107662
Sola-Llano, R, et al. "BOPHYs ." Dyes and pigments : an international journal vol. 170 (2019). doi: https://doi.org/10.1016/j.dyepig.2019.107662
Sola-Llano R, Jiménez J, Avellanal-Zaballa E, Johnson M, Cabreros TA, Moreno F, Maroto BL, Muller G, Bañuelos J, Cerdán L, García-Moreno I, de la Moya S. BOPHYs . Dyes Pigm. 2019 Nov;170. doi: 10.1016/j.dyepig.2019.107662. Epub 2019 Jun 24. PMID: 34054163; PMCID: PMC8157502.
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Dyes Pigm. 2019 Nov;170. doi: 10.1016/j.dyepig.2019.107662. Epub 2019 Jun 24.

BOPHYs .

Dyes and pigments : an international journal

R Sola-Llano, J Jiménez, E Avellanal-Zaballa, M Johnson, T A Cabreros, F Moreno, B L Maroto, G Muller, J Bañuelos, L Cerdán, I García-Moreno, S de la Moya

Affiliations

  1. Departamento de Química Física, Universidad del País Vasco-EHU, Apartado 644, 48080, Bilbao, Spain.
  2. Departamento de Química Orgánica, Facultad de Ciencias Químicas, Universidad Complutense de Madrid, Ciudad Universitaria s/n, 28040, Madrid, Spain.
  3. Department of Chemistry, San José State University, San José, CA 95192-0101, USA.
  4. Departamento de Sistemas de Baja Dimensionalidad, Superficies y Materia Condensada, Instituto de Química Física "Rocasolano", CSIC, Serrano 119, 28006, Madrid, Spain.

PMID: 34054163 PMCID: PMC8157502 DOI: 10.1016/j.dyepig.2019.107662

Abstract

The computationally-aided photophysical and lasing properties of a selected battery of BOPHYs are described and compared to those of related BODIPY counterparts. The present joined theoretical-experimental study helps to put into context the weaknesses and strengths of both dye families under different irradiation conditions. The chemical versatility of the BOPHY scaffold has been also comparatively explored to modulate key photonic properties towards the development of red-emitting dyes, chiroptical dyes and singlet oxygen photosensitizers. Thus, BOPHY BINOLation by fluorine substitution with enantiopure BINOLs endows the BOPHY chromophore with chiroptical activity, as supporting by the simulated circular dichroism, decreasing deeply its fluorescent response due to the promotion of fluorescence-quenching intramolecular charge transfer (ICT). Interestingly, the sole alkylation of the BOPHY core strongly modulates the promotion of ICT, allowing the generation of highly bright BINOL-based BOPHY dyes. Moreover, 3,3'-dibromoBINOLating BOPHYs can easily achieve singlet-oxygen photogeneration, owing to spin-orbit coupling mediated by heavy-atom effect feasible in view of the theoretically predicted disposition of the bromines surrounding the chromophore. From this background, we have established the master guidelines to design bright fluorophores and laser dyes, photosensitizers for singlet oxygen production and chiroptical dyes based on BOPHYs. The possibility to finely mix and balance such properties in a given molecular scaffold outstands BOPHYs as promising dyes competing with the well-settled BODIPY dyes.

Keywords: Charge transfer; Chiral dyes; Fluorescence; Laser dyes; Organic synthesis; Photosensitizers

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