<i>B</i>,<i>B</i>-Diporphyrinbenzyloxy-BODIPY Dyes: Synthesis and Antenna Effect

Brizet, Bertrand; Eggenspiller, Antoine; Gros, Claude P.; Barbe, Jean‐Michel; Goze, Christine; Denat, Franck; Harvey, Pierre D.

doi:10.1021/jo3000833

Cited by 56 publications

(34 citation statements)

References 34 publications

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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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Section: Resultsmentioning

confidence: 99%

Azophenine as Central Core for Efficient Light Harvesting Devices

Karsenti

Harvey

2018

ChemPhysChem

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“…These reactions require strong nucleophilic agents, such as Grignard or organolithium reagents, [4][5][6][7][8][9][10][11][12] and alkoxides, 13,14 or alternatively, can be accomplished under milder reactions in the presence of a Lewis acid (usually AlCl 3 or BF 3 •OEt 2 ). [15][16][17][18][19][20][21] These methodologies afford either the 4-mono-or 4,4'-disubstituted BODIPYs via careful control of the reaction conditions, and additional synthetic steps are required for the preparation of 4,4'-difunctionalized BODIPYs bearing two different substitutents at the boron center. Alternatively, mono-and disubstituted BODIPYs can be prepared by reaction of dipyrrins with haloboranes.…”

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Synthesis of 4,4′-functionalized BODIPYs from dipyrrins

Nguyen

Fronczek

Smith

et al. 2015

Tetrahedron Letters

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“…We surmised that boron functionalization with suitable fluorinated alcohols might provide an effective and versatile way to prepare fluorinated BODIPYs by taking advantage of a large library of already available dyes . Indeed, compounds 2 a and 2 b were prepared according to the route illustrated in Scheme .…”

Section: Resultsmentioning

confidence: 99%

BODIPY Dyes Bearing Multibranched Fluorinated Chains: Synthesis, Structural, and Spectroscopic Studies

Espinoza

Sori

Pizzi

et al. 2019

Chemistry A European J

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A small series of boron‐dipyrromethene (BODIPY) dyes, characterized by the presence of multibranched fluorinated residues, were designed and synthesized. The dyes differ in both the position (para‐perfluoroalkoxy‐substituted phenyl ring or boron functionalization) and number of magnetically equivalent fluorine atoms (27 or 54 fluorine atoms per molecule). Photophysical and crystallographic characterization of the synthesized BODIPYs was carried out to evaluate the effect of the presence of highly fluorinated moieties on the optical and morphological properties of such compounds.

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B,B-Diporphyrinbenzyloxy-BODIPY Dyes: Synthesis and Antenna Effect

Abstract: B,B-Diporphyrinbenzyloxy-BODIPY derivatives have been prepared in high yields, and the photophysical properties are reported. Singlet energy transfers from BODIPY to the porphyrin units have been analyzed.

Cited by 56 publications

References 34 publications

Azophenine as Central Core for Efficient Light Harvesting Devices

Azophenine as Central Core for Efficient Light Harvesting Devices

Synthesis of 4,4′-functionalized BODIPYs from dipyrrins

BODIPY Dyes Bearing Multibranched Fluorinated Chains: Synthesis, Structural, and Spectroscopic Studies

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