Engineering Tuneable Light-Harvesting Systems with Oligothiophene Donors and Mono- or Bis-Bodipy Acceptors

Zrig, Samia; Rémy, Pauline; Andrioletti, Bruno; Rose, Éric; Asselberghs, Inge; Clays, Koen

doi:10.1021/jo702066v

Cited by 54 publications

(33 citation statements)

References 38 publications

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“…When the monodeprotected derivative was the major product (determined by TLC), the reaction was quenched with water and a saturated solution of NH 4 Cl. The product was extracted with dichloromethane, and the organic layers were dried over MgSO 4 .…”

Section: Experimental Section General: [Pdcl 2 a C H T U N G T R E N mentioning

confidence: 99%

“…[2] In recent years, several BODIPY derivatives attached to energy donors such as polycyclic aryl hydrocarbons, [3] oligothiophenes, [4] subphthalocyanines, [5] and to energy acceptors such as porphyrins, [6] perylenediimides, [7] subphthalocyanine, [5,8] fullerenes [9] and BODIPYs [10] have been reported. However, to the best of our knowledge, there is no report about oligo(p-phenylene ethynylene)s (OPEs) as donor or acceptor subunit in the energy-transfer system.…”

Section: Introductionmentioning

confidence: 99%

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Oligo(p‐phenylene ethynylene)–BODIPY Derivatives: Synthesis, Energy Transfer, and Quantum‐Chemical Calculations

Yin

Leen

Jackers

et al. 2011

Chemistry A European J

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The synthesis and energy-transfer properties of a series of oligo(p-phenylene ethynylene)-BODIPY (OPEB) cassettes are reported. A series of oligo(p-phenylene ethynylene)s (OPEs) with different conjugated chain lengths as energy donor subunit in the energy-transfer system were capped at both ends with BODIPY chromophores as energy-acceptor subunits. The effect of the conjugated chain of OPEs on energy transfer in the OPEB cassettes was investigated by UV/Vis and fluorescence spectroscopy and modeling. With increasing number n of phenyl acetylene units (n=1-7), the absorption and emission maxima of OPEn are bathochromically shifted. In the OPEBn analogues, the absorption maximum assigned to the BODIPY moieties is independent of the length of the OPE spacer. However, the relative absorption intensity of the BODIPY band decreases when the number of phenyl acetylene units is increased. The emission spectra of OPEBn are dominated by a band peaking at 613 nm, corresponding to emission of the BODIPY moieties, regardless of whether excitation is at 420 or 550 nm. Furthermore, a very small band is observed with a maximum between 450 and 500 nm, and its intensity relative to that of the BODIPY emission increases with increasing n, that is, the excited state of OPE subunits is efficiently quenched in OPEBn by energy transfer to the BODIPY moieties. Energy transfer (ET) from OPEn to BODIPY in OPEBn is very efficient (all Φ(ET) values are greater than 98 %) and only slightly decreases with increasing length of the OPE units. These results are supported by theoretical studies that show very high energy transfer efficiency (Φ(ET) >75 %) from the OPE spacer to the BODIPY end-groups for chains with up to 15-20 units.

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Section: Experimental Section General: [Pdcl 2 a C H T U N G T R E N mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Oligo(p‐phenylene ethynylene)–BODIPY Derivatives: Synthesis, Energy Transfer, and Quantum‐Chemical Calculations

Yin

Leen

Jackers

et al. 2011

Chemistry A European J

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“…From this, it can be deduced that efficient energy transfer occurs from the perylene units to the nearby BODIPY residue. [15][16][17] On the basis of the timeresolved emission studies, the rate constant for intramolecular energy transfer (k EnT ) must exceed ca. 2.5 ϫ 10 10 s -1 .…”

Section: Photophysics Ofmentioning

confidence: 99%

Energy‐ and Charge‐Transfer Processes in a Perylene–BODIPY–Pyridine Tripartite Array

et al. 2008

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A novel boron dipyrromethene (BODIPY) dye has been synthesized in which the F atoms, usually bound to the boron center, have been replaced with 1-ethynylperylene units and a 4-pyridine residue is attached at the meso-position. The perylene units function as photon collectors over the wavelength range from 350 to 480 nm. Despite an unfavorable spectral overlap integral, rapid energy transfer takes place from the singlet-excited state of the perylene unit to the adjacent BODIPY residue, which is itself strongly fluorescent. The mean energy-transfer time is 7 Ϯ 2 ps at room temperature. The dominant mechanism for the energy-transfer process is Dexter-type electron exchange, with Förster-type dipole-dipole interactions accounting for less than 10 % of the total transfer probability. There are no indications for lightinduced electron transfer in this system, although there is evidence for a nonradiative decay channel not normally seen

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“…dyes/pigments · energy transfer · solar energy · spectroscopy · synthesis design phore [15] with an expanded version [16] in which the spectral overlap term is strongly biased in favour of transfer to the S 2 level. The donor is an aromatic polycycle appended through the boron centre.…”

Section: Introductionmentioning

confidence: 99%

Electronic Energy Transfer to the S₂ Level of the Acceptor in Functionalised Boron Dipyrromethene Dyes

Harriman

Mallon

Goeb

et al. 2009

Chemistry A European J

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Taking the high road: Highly efficient electronic energy transfer takes place from a set of appended aryl polycyclic hydrocarbons to an expanded boron dipyrromethene (Bodipy)-based dye (see figure) despite negligible spectral overlap with the lowest-energy excited state localised on the acceptor.A multi-component array has been constructed around an expanded boron dipyrromethene (Bodipy) dye that absorbs and emits in the far-red region. One of the appendages is a perylene-based moiety that is connected to the boron atom of the terminal Bodipy by a 1,4-diethynylphenylene connector. Despite the fact that there is almost negligible spectral overlap between fluorescence from the perylene unit and absorption by the Bodipy residue, electronic energy transfer is rapid and essentially quantitative. It is concluded that at least half of the photons absorbed by perylene are transferred to the upper-lying singlet excited state (S(2)) associated with the Bodipy-based acceptor. The second appendage is a pyrene unit that is covalently linked to fluorene, through an ethynylene spacer, and to the boron atom of the Bodipy terminus, through a 1,4-diethynylphenylene connector. Pyrene absorbs and emits at higher energy than perylene and there is strong spectral overlap with the Bodipy-based S(2) state, and none with the corresponding S(1) state. Electronic energy transfer is now very fast and exclusively to the S(2) state of the acceptor. It is difficult to compute reasonable estimates for the rates of Coulombic energy transfer, because of uncertainties in the orientation factor, but the principle mechanism is believed to arise from electron exchange. Comparison with an earlier array built around a conventional Bodipy dye indicates that there are comparable electronic coupling matrix elements for the two systems. It is notable that pyrene is more strongly coupled to the Bodipy unit than perylene in both arrays. These new arrays function as highly effective solar concentrators.

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Engineering Tuneable Light-Harvesting Systems with Oligothiophene Donors and Mono- or Bis-Bodipy Acceptors

Cited by 54 publications

References 38 publications

Oligo(p‐phenylene ethynylene)–BODIPY Derivatives: Synthesis, Energy Transfer, and Quantum‐Chemical Calculations

Oligo(p‐phenylene ethynylene)–BODIPY Derivatives: Synthesis, Energy Transfer, and Quantum‐Chemical Calculations

Energy‐ and Charge‐Transfer Processes in a Perylene–BODIPY–Pyridine Tripartite Array

Electronic Energy Transfer to the S₂ Level of the Acceptor in Functionalised Boron Dipyrromethene Dyes

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Engineering Tuneable Light-Harvesting Systems with Oligothiophene Donors and Mono- or Bis-Bodipy Acceptors

Cited by 54 publications

References 38 publications

Oligo(p‐phenylene ethynylene)–BODIPY Derivatives: Synthesis, Energy Transfer, and Quantum‐Chemical Calculations

Oligo(p‐phenylene ethynylene)–BODIPY Derivatives: Synthesis, Energy Transfer, and Quantum‐Chemical Calculations

Energy‐ and Charge‐Transfer Processes in a Perylene–BODIPY–Pyridine Tripartite Array

Electronic Energy Transfer to the S2 Level of the Acceptor in Functionalised Boron Dipyrromethene Dyes

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Product

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Electronic Energy Transfer to the S₂ Level of the Acceptor in Functionalised Boron Dipyrromethene Dyes