Synthesis and fluorescence properties of [60] and [70]fullerene–coumarin dyads: Efficient dipole–dipole resonance energy transfer from coumarin to fullerene

Brites, Maria João; Santos, Célia; Nascimento, Susana; Gigante, Bárbara; Luftmann, Heinrich; Fedorov, Alexander; Berberan‐Santos, Mário N.

doi:10.1039/b601649a

Cited by 40 publications

(28 citation statements)

References 49 publications

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“…The dipole-dipole mechanism of Förster (FRET), which in most cases dominates singlet-singlet energy transfer, was already invoked in previous studies of energy transfer in dyads and polyads with fullerene acting as acceptor [11][12][13][14][15][16][17][18]. In our case, the observed quenching process in the dyads is also consistent with a dominant FRET contribution.…”

Section: /37supporting

confidence: 91%

“…Thus, conformationally rigid D-A systems are obtained affording geometrically well-defined materials. The synthesis and photophysical properties of a series of flexible coumarinfullerene (C 60 and C 70 ) dyads were previously studied by us [15]. To further explore excited-state donor-acceptor interactions in highly conjugated and conformationally rigid D-A systems involving coumarin and C 60 , two new coumarin- [60]fullerene dyads are reported here.…”

Section: Introductionmentioning

confidence: 93%

“…C 60 , well-known as an excellent electron acceptor [4][5][6], has been incorporated in a large variety of molecular structures to form donor-acceptor (D-A) systems [6][7][8]. The excited-state donor-acceptor interactions in such systems, including photoinduced electron and energy transfer, have also been explored [9][10][11][12][13][14][15][16][17][18][19].…”

Section: Introductionmentioning

confidence: 99%

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New coumarin-[60]fullerene dyads connected by an alkynyl linkage: Synthesis and fluorescence studies. Evidence for efficient singlet–singlet energy transfer

et al. 2015

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a b s t r a c tTwo new coumarin-[60]fullerene dyads, in which an alkyne group covalently links C 60 to coumarin, are synthesized via 1,3-dipolar cycloaddition and spectroscopically characterized. Their photophysical properties in apolar (toluene) and polar (THF and benzonitrile) solvents are studied at room temperature, revealing the nature and polarity dependence of the excited-state interactions between the coumarin and C 60 moieties. In both dyads and in all solvents, a strong quenching of the coumarin emission by C 60 was observed. It mainly results from a fast and efficient singletesinglet resonance energy transfer from the coumarin moiety to the C 60 moiety, but an electron transfer contribution, enhanced in polar solvents, also exists. In toluene, the fluorescence emission of the fullerene moiety is increased by the nonradiative energy transfer process, which occurs mainly by a dipoleedipole (FRET) mechanism. In polar solvents (THF and benzonitrile), fast electron transfer from ground-state coumarin to excited fullerene is significant, leading to a partial or complete quenching of the fullerene emission, depending on the dyad.

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Section: /37supporting

confidence: 91%

Section: Introductionmentioning

confidence: 93%

Section: Introductionmentioning

confidence: 99%

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New coumarin-[60]fullerene dyads connected by an alkynyl linkage: Synthesis and fluorescence studies. Evidence for efficient singlet–singlet energy transfer

et al. 2015

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“…Compounds containing poly(ethylene gly col) fragments are widely used in the fullerene chemistry for the synthesis of amphiphilic molecules followed by producing related films, monolayers, composites, 14-16 and spacers separating the fullerene sphere and donor frag ments in molecules of covalently linked donor acceptor dyads. [17][18][19] The presence of the ester group in azide 1 also provides the subsequent functionalization of organo fullerene.…”

mentioning

confidence: 98%

Synthesis of the individual regioisomer of the bisadduct of fullerene C60 with tert-butyl 11-azido-3,6,9-trioxaundecanoate

et al. 2007

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“…N-isopropylacrylamide (NIPAM) was purchased from Wako and used after recrystallization from hexane. 7-(6-Hydroxyhexyloxy)coumarin and 7-(6-hydroxyhexyloxy)-4-methylcoumarin were synthesized according to the literatures [15,16].…”

Section: Introductionmentioning

confidence: 99%

Macroscopic Photoinduced and Reversible Sol-Gel Conversions of Polymer Materials Containing Photoreactive Coumarin Moieties

Moriyama

Okano

Ono

et al. 2015

Trans. Mat. Res. Soc. Japan

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Hydrophilic copolymers containing N-isopropylacrylamide and acrylate with coumarin or 4-methylcoumarin moieties have been synthesized. We reveal that the copolymers with a very small content of coumarin and 4-methylcoumarin units exhibit macroscopic photoinduced and reversible sol-gel conversions. UV light (λ>310 nm) irradiation of aqueous solutions for the copolymers causes the increase in viscosity and the formation of hydrogels, based on photodimerization of coumarin moieties. Subsequent irradiation with UV light (λ=254 nm) of the hydrogels induces the return of fluidity and the change to sol state, due to the decomposition of coumarin dimers. The amount of crosslink structures in the copolymers can be regulated by the reversible photoreaction of coumarin moieties.

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Synthesis and fluorescence properties of [60] and [70]fullerene–coumarin dyads: Efficient dipole–dipole resonance energy transfer from coumarin to fullerene

Cited by 40 publications

References 49 publications

New coumarin-[60]fullerene dyads connected by an alkynyl linkage: Synthesis and fluorescence studies. Evidence for efficient singlet–singlet energy transfer

New coumarin-[60]fullerene dyads connected by an alkynyl linkage: Synthesis and fluorescence studies. Evidence for efficient singlet–singlet energy transfer

Synthesis of the individual regioisomer of the bisadduct of fullerene C60 with tert-butyl 11-azido-3,6,9-trioxaundecanoate

Macroscopic Photoinduced and Reversible Sol-Gel Conversions of Polymer Materials Containing Photoreactive Coumarin Moieties

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