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Review
. 2021 Apr 14;12(19):6607-6628.
doi: 10.1039/d1sc00732g.

Design of BODIPY dyes as triplet photosensitizers: electronic properties tailored for solar energy conversion, photoredox catalysis and photodynamic therapy

Elena Bassan  1 , Andrea Gualandi  1 , Pier Giorgio Cozzi  1 , Paola Ceroni  1
Affiliations
Review

Design of BODIPY dyes as triplet photosensitizers: electronic properties tailored for solar energy conversion, photoredox catalysis and photodynamic therapy

Elena Bassan et al. Chem Sci. .

Abstract

BODIPYs are renowned fluorescent dyes with strong and tunable absorption in the visible region, high thermal and photo-stability and exceptional fluorescence quantum yields. Transition metal complexes are the most commonly used triplet photosensitisers, but, recently, the use of organic dyes has emerged as a viable and more sustainable alternative. By proper design, BODIPY dyes have been turned from highly fluorescent labels into efficient triplet photosensitizers with strong absorption in the visible region (from green to orange). In this perspective, we report three design strategies: (i) halogenation of the dye skeleton, (ii) donor-acceptor dyads and (iii) BODIPY dimers. We compare pros and cons of these approaches in terms of optical and electrochemical properties and synthetic viability. The potential applications of these systems span from energy conversion to medicine and key examples are presented.

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Conflict of interest statement

There are no conflicts to declare.

Figures

Fig. 1
Fig. 1. Structure of the BODIPY core and IUPAC numeration.
Fig. 2
Fig. 2. Jablonski diagram for organic molecules with radiative (straight lines) and non-radiative processes (wavy lines).
Scheme 1
Scheme 1
Fig. 3
Fig. 3. Population of triplet excited state T1 by radical-pair intersystem crossing (RP-ISC) or by spin–orbit charge transfer intersystem crossing (SOCT-ISC).
Scheme 2
Scheme 2
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Scheme 5
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Scheme 8
Fig. 4
Fig. 4. Jablonski diagram illustrating the energies of the excited states involved in the SOCT-ISC mechanism (A) and related Marcus curve (B).
Scheme 9
Scheme 9
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Scheme 11
Fig. 5
Fig. 5. Simplified Jablonski diagram illustrating the main excited states' energy levels and processes involved in TTA upconversion. In this example, A = BDP-PTZ and B = perylene.
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Scheme 12
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Scheme 19
Fig. 6
Fig. 6. Historical development of BODIPY dyes.
None
Prof. Paola Ceroni, second row on the left; Ms Elena Bassan first row on the left; Prof. Pier Giorgio Cozzi, second row on the right; Dr Andrea Gualandi, second row on the right.
See this image and copyright information in PMC

References

    1. El-Khouly M. E. Fukuzumi S. D'Souza F. ChemPhysChem. 2014;15:30–47. - PubMed
    1. Niu L. Y. Li H. Feng L. Guan Y. S. Chen Y. Z. Duan C. F. Wu L. Z. Guan Y. F. Tung C. H. Yang Q. Z. Anal. Chim. Acta. 2013;775:93–99. - PubMed
    1. Kowada T. Kikuchi K. Chem. Soc. Rev. 2015:4953–4972. - PubMed
    1. Kamkaew A. Lim S. H. Lee H. B. Kiew L. V. Chung L. Y. Burgess K. Chem. Soc. Rev. 2013;42:77–88. - PMC - PubMed
    1. Nepomnyashchii A. B. Bard A. J. Acc. Chem. Res. 2012;45:1844–1853. - PubMed

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