Novel [60]fullerene–TTF cyclohexene fused polyadducts: unprecedented tri- and tetra-Diels–Alder adducts of dimethylidene[2H]tetrathiafulvalenes with C60

Kréher, David; Liu, Shenggao; Cariou, M.; Hudhomme, Piétrick; Gorgues, A.; Mas, M.; Veciana, Jaume; Rovira, Concepció

doi:10.1016/s0040-4039(01)00494-4

Cited by 27 publications

(13 citation statements)

References 24 publications

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“…Consequently, in order to optimize their selective synthesis, we considered their obtention in much higher yields by successive similar treatments of the major adducts produced at each step. 59 Starting from monoadducts 1A, the subsequent cycloaddition of 1A with diene 6 was responsible for the formation of diadducts 1B. Secondly, applying the same methodology by starting from 1B, we could reach and isolate the desired triadducts 1C and tetraadducts 1D in acceptable yields (Scheme 15).…”

Section: Synthesis Of Ttf-c 60 Dyads and (Ttf) N -C 60 Polyadsmentioning

confidence: 99%

“…Secondly, applying the same methodology by starting from 1B, we could reach and isolate the desired triadducts 1C and tetraadducts 1D in acceptable yields (Scheme 15). 59 All compounds 1A-D were separated by column chromatography, but the isolation of polyadducts appeared to be highly dependent on the chromatographic conditions: first, some of these polyadducts appeared not to be stable in chlorinated solvents, except in the case where the TTF core is bearing polyethersulfanyl groups. Secondly, due to the poor solubility of some adducts, we used mixtures of solvents (carbon disulfide, dichloromethane or toluene) as eluent.…”

Section: Synthesis Of Ttf-c 60 Dyads and (Ttf) N -C 60 Polyadsmentioning

confidence: 99%

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Rigidified tetrathiafulvalene–[60]fullerene assemblies: towards the control of through-space orientation between both electroactive units

et al. 2002

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Our recent works on fused TTF-C 60 dyads, (TTF) n -C 60 polyads and C 60 -TTF-C 60 dumbbell triads in which the acceptor C 60 is doubly tethered to the donor tetrathiafulvalene through a rigidified cyclohexene ring are presented. This approach was developed in order to control the relative orientation as well as the distance between both donor and acceptor entities. Thereby, through-space interactions which are of great importance for photoinduced electron-and/or energy-transfer processes are expected to dominate because of the special topology of the molecules. The two linked C 60 and TTF chromophores in such adducts are not only in close proximity but also have optimal orbital orientations, thus facilitating these through-space electronic interactions. These new C 60 -based assemblies were synthesized by [4 1 2] Diels-Alder cycloaddition reactions. The different methodologies considered for their synthesis are discussed, their analytical, spectroscopic characterizations and electrochemical properties are also described. The selective electro-oxidation or reduction afforded the corresponding radical cation and radical anion which were characterized by EPR. These C 60 -based assemblies were studied for their nonlinear optical and optical limiting applications. Moreover, intramolecular photoinduced charge-separation and charge-recombination processes in a fused C 60 -TTF-C 60 dumbbell triad which was designed to be soluble in organic solvents were investigated by time-resolved absorption and fluorescence techniques. Appreciable interaction between the C 60 moiety and TTF moiety in the ground state was suggested by steady-state absorption spectra and the fluorescence spectra showed considerable interaction in the singlet excited state. The nanosecond transient absorption spectra displayed the formation of the chargeseparated radical pair C 60 -TTF ? 1 -C 60 ? 2 , characterized by a lifetime of ca. 20 ns in benzonitrile.

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Section: Synthesis Of Ttf-c 60 Dyads and (Ttf) N -C 60 Polyadsmentioning

confidence: 99%

Section: Synthesis Of Ttf-c 60 Dyads and (Ttf) N -C 60 Polyadsmentioning

confidence: 99%

Rigidified tetrathiafulvalene–[60]fullerene assemblies: towards the control of through-space orientation between both electroactive units

et al. 2002

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“…Scheme 12. methyl)TTF with naked iodide in the presence of C60 according to Scheme 9. More interestingly, their synthesis was considered in higher yields using an iterative strategy by successive treatments of the major adducts produced at each step (Scheme 13) [65]. Nevertheless, the tedious isolation and characterization of the different regioisomers has not been carried out for polyads 33.…”

Section: Multiple Cycloadditions Of Ttf Onto C60mentioning

confidence: 99%

Diels–Alder cycloaddition as an efficient tool for linking π-donors onto fullerene C60

Hudhomme

2006

Comptes Rendus. Chimie

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“…In one of our recent papers [13] the eight regioisomers of the triad C 60 -(TTF) 2 in which the TTF is substituted with pentylsulfanyl groups were analytically separated by HPLC. All the community agree that it is a very fastidious and difficult work to separate the different regioisomers in triads.…”

Section: Bis-linkedmentioning

confidence: 99%

“…Here, it is necessary to notice, that the investigated adducts appear as a mixture of several regioisomers, e.g., there are eight regioisomers in the triads, [13] which makes the normal mode calculations very complicated. The frequencies of these bands are fairly the same for all investigated compounds.…”

Section: Bis-linkedmentioning

confidence: 99%

SPECTRAL STUDIES OF THEBIS-LINKED TETRATHIAFULVALENES (TTFs) TO [60]FULLERENE

Olejniczak¹,

Bogucki²,

Golub³

et al. 2002

Fullerenes, Nanotubes and Carbon Nanostructures

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Results of the first extended spectral investigation of the bis-linked tetrathiafulvalene donors (TTFs) to [60]fullerene are reported. From UV-VIS-NIR-IR spectra it is stated that charge distribution on C 60 moiety and on TTFs attachments is disturbed after the adduct formation. This redistribution depends not only on the nature of an attached molecular group but also on the number of bounded donors. In the infrared spectra of the bisadducts, a particularly strong resonant effect was observed.

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Novel [60]fullerene–TTF cyclohexene fused polyadducts: unprecedented tri- and tetra-Diels–Alder adducts of dimethylidene[2H]tetrathiafulvalenes with C60

Cited by 27 publications

References 24 publications

Rigidified tetrathiafulvalene–[60]fullerene assemblies: towards the control of through-space orientation between both electroactive units

Rigidified tetrathiafulvalene–[60]fullerene assemblies: towards the control of through-space orientation between both electroactive units

Diels–Alder cycloaddition as an efficient tool for linking π-donors onto fullerene C60

SPECTRAL STUDIES OF THEBIS-LINKED TETRATHIAFULVALENES (TTFs) TO [60]FULLERENE

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