“Scorpion”-shaped mono(carboxy)porphyrin-(BODIPY)<sub>2</sub>, a novel triazine bridged triad: synthesis, characterization and dye sensitized solar cell (DSSC) applications

Galateia, Zervaki E.; Agapi, Nikiforou; Nikolaou, Vasilis; Sharma, Ganesh D.; Athanassios, Coutsolelos G.

doi:10.1039/c4tc02902j

Cited by 41 publications

(14 citation statements)

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“… 34 – 39 Incorporation of BODIPY dyes into the triazene core has also been reported 40 and these types of systems were used as sensors (especially in metal ion recognition) 41 , 42 as well as components of the dye-sensitized solar cells. 43 , 44 …”

Section: Resultsmentioning

confidence: 99%

A triazine-based BODIPY trimer as a molecular viscometer

Raut

Kimball

Fudala

et al. 2016

Phys. Chem. Chem. Phys.

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Section: Resultsmentioning

confidence: 99%

A triazine-based BODIPY trimer as a molecular viscometer

Raut

Kimball

Fudala

et al. 2016

Phys. Chem. Chem. Phys.

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“…In addition, Ho et al illustrated that a covalently connected BODIPY-(Zn)Porphyrin dye exhibits 12 800 TONs over 120 h of illumination . It is worth mentioning that multichromophoric systems have also been reported to effectively enhance the photovoltaic performance in dye-sensitized solar cells (DSSCs). , Porphyrin-BODIPY dyads have been thoroughly examined as sensitizers in DSSCs due to the antenna effect between the chromophores and also because of their complementary absorption features. − In stark contrast, there is only one example of a porphyrin-BODIPY dyad in DSPs for H 2 evolution . However, several aspects that could impact H 2 evolution are still not studied in such porphyrin-BODIPY systems, namely, the type of connection between the two entities or the supplementary antenna effect by the addition of an extra BODIPY.…”

Section: Introductionmentioning

confidence: 99%

Antenna Effect in BODIPY-(Zn)Porphyrin Entities Promotes H₂ Evolution in Dye-Sensitized Photocatalytic Systems

Nikolaou

Charalambidis

Λάνδρου

et al. 2021

ACS Appl. Energy Mater.

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In this study, we report the utilization of BODIPY-(Zn)Porphyrin hybrids in photocatalytic H2 production from water. These entities were applied as photosensitizers upon their chemisorption onto the surface of platinum-doped titanium dioxide nanoparticles (Pt-TiO2), which acted as photocatalysts. To evaluate the impact of the different connectivity between the chromophores in photocatalytic in H2 evolution, we employed two diverse BODIPY-(Zn)Porphyrin entities, in which the BODIPY moiety is either covalently attached (BDP-Por) or axially coordinated (BDP(Im)-Por) with the (Zn)Porphyrin. The covalently connected dyad (BDP-Por) presented higher catalytic activity (17 500 TONs) compared to the axial coordinated (BDP(Im)-Por, 13 700 TONs). In BDP-Por dyad, an additional BDP(Im) moiety was introduced and the formed hybrid (BDP-Por-BDP(Im)) outperformed the aforementioned systems, due to the enhanced light harvesting ability. Overall, we developed highly efficient dye-sensitized photocatalytic systems (DSPs) based on noble-metal-free photosensitizers reaching 18 600 turnover numbers (TONs) and 225 mmol(H2) g(cat)−1 h–1.

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“…Such tailoring of the molecular structure being available enables the modulation of the spectral bands of the BODIPY, leading to stable and bright dyes along the whole visible spectrum and even reaching the near-infrared region (Lu et al, 2014; Bañuelos, 2016). Multichromophoric dyes based on the BODIPY core are currently being intensively applied in various technological fields such as photovoltaics (Galateia et al, 2015), photosynthetic antennae (Ke et al, 2017), sensing and electronics (Squeo et al, 2017), electrochemistry (Qi et al, 2013), near-infrared emitters (Sakamoto et al, 2012), and as photosensitizers and labeling tools in biomedicine (Turksoy et al, 2019).…”

Section: Introductionmentioning

confidence: 99%

Tuning the Photonic Behavior of Symmetrical bis-BODIPY Architectures: The Key Role of the Spacer Moiety

et al. 2019

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Herein we describe the synthesis, computationally assisted spectroscopy, and lasing properties of a new library of symmetric bridged bis-BODIPYs that differ in the nature of the spacer. Access to a series of BODIPY dimers is straightforward through synthetic modifications of the pending ortho-hydroxymethyl group of readily available C-8 (meso) ortho-hydroxymethyl phenyl BODIPYs. In this way, we have carried out the first systematic study of the photonic behavior of symmetric bridged bis-BODIPYs, which is effectively modulated by the length and/or stereoelectronic properties of the spacer unit. The designed bis-BODIPYs display bright fluorescence and laser emission in non-polar media. The fluorescence response is governed by the induction of a non-emissive intramolecular charge transfer (ICT) process, which is significantly enhanced in polar media. The effectiveness of the fluorescence quenching and also the prevailing charge transfer mechanism (from the spacer itself or between the BODIPY units) rely directly on the electron-releasing ability of the spacer. Moreover, the linker moiety can also promote intramolecular excitonic interactions, leading to excimer-like emission characterized by new spectral bands and the lengthening of lifetimes. The substantial influence of the bridging moiety on the emission behavior of these BODIPY dyads and their solvent-sensitivity highlight the intricate molecular dynamics upon excitation in multichromophoric systems. In this regard, the present work represents a breakthrough in the complex relationship between the molecular structure of the chromophores and their photophysical signatures, thus providing key guidelines for rationalizing the design of tailored bis-BODIPYs with potential advanced applications.

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“Scorpion”-shaped mono(carboxy)porphyrin-(BODIPY)₂, a novel triazine bridged triad: synthesis, characterization and dye sensitized solar cell (DSSC) applications

Abstract: A novel BODIPY-porphyrin triad is prepared with two BODIPY molecules covalently attached via a 1,3,5-triazine molecule to a free-base carboxyphenyl meso-substituted porphyrin.

Cited by 41 publications

References 100 publications

A triazine-based BODIPY trimer as a molecular viscometer

A triazine-based BODIPY trimer as a molecular viscometer

Antenna Effect in BODIPY-(Zn)Porphyrin Entities Promotes H₂ Evolution in Dye-Sensitized Photocatalytic Systems

Tuning the Photonic Behavior of Symmetrical bis-BODIPY Architectures: The Key Role of the Spacer Moiety

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“Scorpion”-shaped mono(carboxy)porphyrin-(BODIPY)2, a novel triazine bridged triad: synthesis, characterization and dye sensitized solar cell (DSSC) applications

Abstract: A novel BODIPY-porphyrin triad is prepared with two BODIPY molecules covalently attached via a 1,3,5-triazine molecule to a free-base carboxyphenyl meso-substituted porphyrin.

Cited by 41 publications

References 100 publications

A triazine-based BODIPY trimer as a molecular viscometer

A triazine-based BODIPY trimer as a molecular viscometer

Antenna Effect in BODIPY-(Zn)Porphyrin Entities Promotes H2 Evolution in Dye-Sensitized Photocatalytic Systems

Tuning the Photonic Behavior of Symmetrical bis-BODIPY Architectures: The Key Role of the Spacer Moiety

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“Scorpion”-shaped mono(carboxy)porphyrin-(BODIPY)₂, a novel triazine bridged triad: synthesis, characterization and dye sensitized solar cell (DSSC) applications

Antenna Effect in BODIPY-(Zn)Porphyrin Entities Promotes H₂ Evolution in Dye-Sensitized Photocatalytic Systems