RT Journal Article
T1 BOPHYs versus BODIPYs: A comparison of their performance as effective multi-function organic dyes
A1 Sola Llano, Rebeca
A1 Jiménez, J.
A1 Avellanal Zaballa, Edurne
A1 Johnson, M.
A1 Cabreros, Trevor A.
A1 Moreno Jiménez, Florencio
A1 Maroto, Beatriz Lora
A1 Muller, Gilles
A1 Bañuelos Prieto, Jorge
A1 Cerdán Pedraza, Luis
A1 García Moreno, Inmaculada
A1 Moya Cerero, Santiago de la
AB 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 angiven molecular scaffold outstands BOPHYs as promising dyes competing with the well-settled BODIPY dyes
PB Elsevier
SN 0143-7208
YR 2019
FD 2019-06-24
LK https://hdl.handle.net/20.500.14352/12726
UL https://hdl.handle.net/20.500.14352/12726
LA eng
NO Received 13 May 2019; Received in revised form 27 May 2019; Accepted 23 June 2019; Available online 24 June 2019
NO Ministerio de Economía y Competitividad (MINECO)
NO Gobierno Vasco
NO Comunidad de Madrid
NO Universidad Complutense de Madrid
DS Docta Complutense
RD 6 may 2024