meso-2′-Linked porphyrin–BODIPY hybrids: synthesis and efficient excitation energy transfer

Hu, Qin-Qin; Zhu, Yi‐Zhou; Zhang, Shaochun; Tong, Yu‐Zhang; Zheng, Jian‐Yu

doi:10.1039/c5dt01184a

Cited by 20 publications

(7 citation statements)

References 76 publications

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“…The incorrect matching on the Soret band (around 430 nm) is due to the too high absorbance (>0.5) on this transition inherent of its high extinction coefficient. Overall, all of the experiments indicate an almost quantitative energy transfer from BODIPY to porphyrin and are in agreement with previous works in which similar chromophores have been utilized. ,,− For transient absorption studies comparing the charge carrier properties of Pt-TiO 2 NPs with TiO 2 NPs, see the Supporting Information.…”

Section: Resultssupporting

confidence: 88%

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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Section: Resultssupporting

confidence: 88%

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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“…Femtosecond transient absorption spectra for BDP-TTP and 3BDP-TTP are shown in Figure 5a and Figure 6a, respectively, with 524 nm pump wavelength. Transient absorption spectra of studied BODIPY-porphyrin compounds exhibited similar features, as compared to the literature [52,53]. As seen in these figures, the bleaching signal at the 524 nm has ascribed to the saturation of the singlet state of the BODIPY unit.…”

Section: Ultrafast Pump-probe Spectroscopy Measurementssupporting

confidence: 74%

Ultrafast Electron/Energy Transfer and Intersystem Crossing Mechanisms in BODIPY-Porphyrin Compounds

et al. 2021

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Meso-substituted borondipyrromethene (BODIPY)-porphyrin compounds that include free base porphyrin with two different numbers of BODIPY groups (BDP-TTP and 3BDP-TTP) were designed and synthesized to analyze intramolecular energy transfer mechanisms of meso-substituted BODIPY-porphyrin dyads and the effect of the different numbers of BODIPY groups connected to free-base porphyrin on the energy transfer mechanism. Absorption spectra of BODIPY-porphyrin conjugates showed wide absorption features in the visible region, and that is highly valuable to increase light-harvesting efficiency. Fluorescence spectra of the studied compounds proved that BODIPY emission intensity decreased upon the photoexcitation of the BODIPY core, due to the energy transfer from BODIPY unit to porphyrin. In addition, ultrafast pump-probe spectroscopy measurements indicated that the energy transfer of the 3BDP-TTP compound (about 3 ps) is faster than the BDP-TTP compound (about 22 ps). Since the BODIPY core directly binds to the porphyrin unit, rapid energy transfer was seen for both compounds. Thus, the energy transfer rate increased with an increasing number of BODIPY moiety connected to free-base porphyrin.

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“…Polyads exhibiting 1 Bodipy*→porphyrin processes is well documented . In order to explain this fast rate for 1 Bodipy*→porphyrin in P 2 B 2 Q , comparisons with some literature examples are provided (Figure : D1 , D2 , D3 , D4 , D5 , D6 , D7 , D8 , D9 , D10 , D11 , D12 , and D13 . This series can be separated into three sub‐series: D1 – D5 (through space), D6–D9 (through bond), and D10–D13 (directly bonded).…”

Section: Resultsmentioning

confidence: 99%

Azophenine as Central Core for Efficient Light Harvesting Devices

Karsenti

Harvey

2018

ChemPhysChem

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The notoriously non-luminescent uncycled azophenine (Q) was harnessed with Bodipy and zinc(II)porphyrin antennas to probe its fluorescence properties, its ability to act as a singlet excited state energy acceptor and to mediate the transfer. Two near-IR emissions are depicted from time-resolved fluorescence spectroscopy, which are most likely due to the presence of tautomers of very similar calculated total energies (350 cm ; DFT; B3LYP). The rates for energy transfer, k (S ), for Bodipy*→Q are in the order of 10 -10 s and are surprisingly fast when considering the low absorptivity properties of the lowest energy charge transfer excited state of azophenine. The rational is provided by the calculated frontier molecular orbitals (MOs) which show atomic contributions in the C H C≡CC H arms, thus favoring the double electron exchange mechanism. In the mixed-antenna Bodipy-porphyrin star molecule, the rate for Bodipy*→porphyrin has also been evaluated (≈16×10 s ) and is among the fastest rates reported for Bodipy-zinc(II)porphyrin pairs. This astonishing result is again explained from the atomic contributions of the C H C≡CC H and C≡CC H arms thus favouring the Dexter process. Here, for the first time, this process is found to be sensitively temperature-dependent. The azophenine turns out to be excellent for electronic communication.

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meso-2′-Linked porphyrin–BODIPY hybrids: synthesis and efficient excitation energy transfer

Cited by 20 publications

References 76 publications

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

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

Ultrafast Electron/Energy Transfer and Intersystem Crossing Mechanisms in BODIPY-Porphyrin Compounds

Azophenine as Central Core for Efficient Light Harvesting Devices

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meso-2′-Linked porphyrin–BODIPY hybrids: synthesis and efficient excitation energy transfer

Cited by 20 publications

References 76 publications

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

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

Ultrafast Electron/Energy Transfer and Intersystem Crossing Mechanisms in BODIPY-Porphyrin Compounds

Azophenine as Central Core for Efficient Light Harvesting Devices

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

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