Switching the photo-induced energy and electron-transfer processes in BODIPY–phthalocyanine conjugates

Liu, Jian-Yong; Ermilov, Eugeny; Röder, Beate; Ng, Dennis K. P.

doi:10.1039/b821630d

Cited by 75 publications

(39 citation statements)

References 20 publications

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“…This shows that an electron-transfer process is switched off for the non-styryl-BODIPY analogue upon phthalocyanine excitation, but switched on in the styryl-BODIPY analogue. 25 Energy transfer to the BODIPY can be achieved through careful selection of both the BODIPY used and the attached fluorophore. Energy transfer from the silicon phthalocyanine to the BODIPY is energetically unfavourable, due to the lower-energy light that is absorbed by the silicon phthalocyanine being unable to promote an electron into the higher energy LUMO of the BODIPY, but, by using a sub-phthalocyanine and a di-styryl-BODIPY, energy transfer to the BODIPY does occur.…”

Section: Through-space Energy-transfer Cassettesmentioning

confidence: 99%

4,4′-Difluoro-4-bora-3a,4a-diaza-s-indacenes (BODIPYs) as components of novel light active materials

2011

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Section: Through-space Energy-transfer Cassettesmentioning

confidence: 99%

4,4′-Difluoro-4-bora-3a,4a-diaza-s-indacenes (BODIPYs) as components of novel light active materials

2011

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“…[1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16][17][18][19][20] In this marvelous process, sunlight is harvested by the antenna complexes and the excitation energy is funneled to the reaction center (RC), where multistep electron-transfer reactions occur to generate a potential that can drive chemical reactions ( Figure 1). [34][35][36] Through a survey of the literature, one finds that tetrapyrrole macrocycles, such as porphyrins [37][38][39][40][41][42][43][44][45][46][47][48][49][50][51][52][53] and phthalocyanines, [54][55][56][57][58][59][60][61]…”

Section: Introductionmentioning

confidence: 99%

Photosynthetic Antenna–Reaction Center Mimicry by Using Boron Dipyrromethene Sensitizers

2013

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Various molecular and supramolecular systems have been synthesized and characterized recently to mimic the functions of photosynthesis, in which solar energy conversion is achieved. Artificial photosynthesis consists of light-harvesting and charge-separation processes together with catalytic units of water oxidation and reduction. Among the organic molecules, derivatives of BF2-chelated dipyrromethene (BODIPY), "porphyrin's little sister", have been widely used in constructing these artificial photosynthetic models due to their unique properties. In these photosynthetic models, BODIPYs act as not only excellent antenna molecules, but also as electron-donor and -acceptor molecules in both the covalently linked molecular and supramolecular systems formed by axial coordination, hydrogen bonding, or crown ether complexation. The relationships between the structures and photochemical reactivities of these novel molecular and supramolecular systems are discussed in relation to the efficiency of charge separation and charge recombination. Femto- and nanosecond transient absorption and photoelectrochemical techniques have been employed in these studies to give clear evidence for the occurrence of energy- and electron-transfer reactions and to determine their rates and efficiencies.

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“…[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%

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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Switching the photo-induced energy and electron-transfer processes in BODIPY–phthalocyanine conjugates

Abstract: Two novel silicon(IV) phthalocyanines substituted axially with two BODIPY or mono-styryl BODIPY moieties have been synthesised, which exhibit predominantly a photo-induced energy or electron-transfer process in toluene depending on the axial substituents.

Cited by 75 publications

References 20 publications

4,4′-Difluoro-4-bora-3a,4a-diaza-s-indacenes (BODIPYs) as components of novel light active materials

4,4′-Difluoro-4-bora-3a,4a-diaza-s-indacenes (BODIPYs) as components of novel light active materials

Photosynthetic Antenna–Reaction Center Mimicry by Using Boron Dipyrromethene Sensitizers

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

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