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BODIPYs: State of the Art and Future Perspectives

A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Colorants".

Deadline for manuscript submissions: 31 July 2025 | Viewed by 763

Special Issue Editors


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Guest Editor
Departamento de Química Física, Facultad de Ciencia y Tecnología, Universidad del País Vasco-EHU, Apartado 644, 48080 Bilbao, Spain
Interests: organic dyes; fluorescence; photonics; computational chemistry; materials chemistry
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Guest Editor Assistant
Departamento de Química Física, Facultad de Ciencia y Tecnología, Universidad del País Vasco-EHU, Apartado 644, 48080 Bilbao, Spain
Interests: fluorescent dyes; spectroscopy; biophotonics; chemosensors; laser spectroscopy; quantum mechanics

Special Issue Information

Dear Colleagues,

BODIPYs (boron dipyrromethenes; 4-bora-3a,4a-diaza-s-indacenes) constitute one of the most valuable families of technological dyes, as supported by the increasing number of publications in the recent few years. Nowadays, there is a plethora of available synthetic procedures for their direct functionalization, focused on appropriate modulation of key physical (mainly photophysical) properties. This chemical versatility is, indeed, the main reason of its success. Its ample reactivity allows the derivatization of BODIPYs at their dipyrrin moieties with a great variety of pendant functional groups, and, accordingly, the photophysical signatures can be deeply and finely modulated. In this way, tailor-made BODIPYs can be developed with specific and improved properties. Therefore, BODIPYs have been tested in a myriad of applications, such as fluorescence sensors, switches and probes, as tunable laser dyes, in light harvesting arrays for antenna systems, in photovoltaic devices, in optoelectronics, in biomedicine, as fluorescence markers for bioimaging, as singlet-oxygen generators in photodynamic therapy, and in chirality where the fluorophore responds to circular polarized light, to name a few of the most relevant application fields. This Special Issue intends to overview the state of the art of BODIPYs, remarking the recent advances in the chemistry of BODIPYs and the main outcomes in diverse fields where they are applied, as well as to provide some guidelines about how they are perceived.

Dr. Jorge Bañuelos Prieto
Guest Editor

Dr. Edurne Avellanal-Zaballa
Guest Editor Assistant

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Keywords

  • BODIPYs
  • spectroscopy
  • synthesis
  • quantum mechanics
  • tunable laser
  • bioimaging
  • photodynamic therapy
  • optoelectronics

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Published Papers (2 papers)

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Research

20 pages, 2332 KiB  
Article
Photophysical Properties and Protein Binding Studies of Piperazine-Substituted Anthracene-BODIPY Dyads for Antimicrobial Photodynamic Therapy
by Stephen O’Sullivan, Leila Tabrizi, Kaja Turzańska, Ian P. Clark, Deirdre Fitzgerald-Hughes and Mary T. Pryce
Molecules 2025, 30(13), 2727; https://doi.org/10.3390/molecules30132727 - 25 Jun 2025
Viewed by 240
Abstract
This work presents the synthesis, characterisation, photophysical properties, time-resolved spectroscopic behaviour, and biological evaluation of two structurally distinct heavy-atom-free BODIPY-anthracene dyads (BDP-1) and the newly designed 2,6-bis[1-(tert-butyl) 4-(prop-2-yn-1-yl) piperazine-1,4-dicarboxylate] BODIPY-anthracene (BDP-2), incorporating 2,6-alkynyl-piperazine substituents for potential application in antimicrobial [...] Read more.
This work presents the synthesis, characterisation, photophysical properties, time-resolved spectroscopic behaviour, and biological evaluation of two structurally distinct heavy-atom-free BODIPY-anthracene dyads (BDP-1) and the newly designed 2,6-bis[1-(tert-butyl) 4-(prop-2-yn-1-yl) piperazine-1,4-dicarboxylate] BODIPY-anthracene (BDP-2), incorporating 2,6-alkynyl-piperazine substituents for potential application in antimicrobial photodynamic therapy. BDP-1 exhibits absorption and emission maxima at 507 nm and 516 nm, respectively, with a Stokes shift of 344 cm−1 in dichloromethane (DCM), characteristic of unsubstituted BODIPYs. In contrast, BDP-2 undergoes a red-shift in the absorption maximum to 552 nm (Stokes shift of 633 cm−1), which is attributed to the extended conjugation from the introduction of the alkyne groups. Time-resolved infrared spectroscopy confirmed efficient spin-orbit charge transfer intersystem crossing, and nanosecond transient absorption studies confirmed the formation of a long-lived triplet state for BDP-2 (up to 138 µs in MeCN). A binding constant (Kb) of 9.6 × 104 M−1 was obtained for BDP-2 when titrated with bovine serum albumin (BSA), which is higher than comparable BODIPY derivatives. BDP-2 displayed improved hemocompatibility compared to BDP-1 (<5% haemolysis of human erythrocytes up to 200 μg·mL−1). Antimicrobial activity of BDP-1 and BDP-2 was most potent when irradiated at 370 nm compared to the other wavelengths employed. However, BDP-2 did not retain the potent (6 log) and rapid (within 15 min) eradication of Staphylococcus aureus achieved by BDP-1 under irradiation at 370 nm. These findings demonstrate the rational design of BDP-2 as a biocompatible, and heavy-atom-free BODIPY offering promise for targeted antimicrobial photodynamic therapeutic applications. Full article
(This article belongs to the Special Issue BODIPYs: State of the Art and Future Perspectives)
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21 pages, 2646 KiB  
Article
BOPAM’s Bright and Dark Excited States: Insight from Structural, Photophysical, and Quantum Chemical Investigations
by Kexin Yu, Thanh Chung Pham, Jianjun Huang, Yixuan Li, Luc Van Meervelt, Mark Van der Auweraer, Daniel Escudero and Wim Dehaen
Molecules 2025, 30(13), 2673; https://doi.org/10.3390/molecules30132673 - 20 Jun 2025
Viewed by 153
Abstract
BOPAM exhibits high fluorescence quantum yields, along with exceptional photostability, rendering it a promising platform for applications as fluorescence sensors. However, the development of BOPAM-based fluorophores with extended emission wavelengths remains limited, and the underlying mechanisms of fluorescence quenching via the population of [...] Read more.
BOPAM exhibits high fluorescence quantum yields, along with exceptional photostability, rendering it a promising platform for applications as fluorescence sensors. However, the development of BOPAM-based fluorophores with extended emission wavelengths remains limited, and the underlying mechanisms of fluorescence quenching via the population of dark twisted intramolecular charge transfer (1TICT) excited states are not yet fully understood. To address these gaps, we synthesized a series of BOPAM derivatives by incorporating electron-donating groups at the boron atoms and the phenyl rings of the BOPAM core. The introduction of bromide, phenyl, and naphthyl groups preserved the intrinsic locally excited (1LE) emission of BOPAM. In contrast, the incorporation of diphenylamine (BP-DA) and triphenylamine (BP-TA) moieties resulted in a red-shifted emission, attributed to an enhanced intramolecular charge transfer (ICT) process. Notably, in acetonitrile, BP-DA exhibited weak fluorescence originating from a 1TICT state, which was populated via the S21TICT transition. Furthermore, the emission observed from BP-TA was associated with a higher-lying excited state, likely the initially populated S2 state possessing a 1LE character. These findings not only introduce novel red-emissive BOPAM-based fluorophores, but also offer valuable insights into the role of the S2 state in governing fluorescence quenching mechanisms in BOPAM derivatives. Full article
(This article belongs to the Special Issue BODIPYs: State of the Art and Future Perspectives)
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