The bis-adducts of the [5,6]-fullerene C60 and anthracene

Duarte-Ruiz, Álvaro; Müller, Thomas; Wurst, Klaus; Kräutler, Bernhard

doi:10.1016/s0040-4020(01)00237-x

Cited by 49 publications

(43 citation statements)

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“…1). The same spectral features were also observed in the more stable tris-orthogonal (or e,e,e) trisadduct of anthracene with [5,6]fullerene C 60 (1) [29]. In solution and at ambient temperature, the tris-adduct 2 decomposed within minutes (first to the equatorial ebisadduct e-1-A 2 and then to the monoadduct 1-A 1 ).…”

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confidence: 55%

“…3), but the molecules did not show shape-complementary intermolecular contacts. Shape-complementary, regular intermolecular contacts between concave [4 þ 2] cycloaddends and the convex fullerene sphere of a neighbor [5,6]fullerene molecule have been observed in a variety of crystal structures with C 60 : e.g., in the [4 þ 2] cycloadducts of 1 with cyclohexa-1,3-diene [22], in mono-and bis- adducts with anthracene [30] [31], and in cocrystals of C 60 and triptycene [32] and with biconcave porphyrins [33].…”

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confidence: 99%

“…The trisadduct 2 crystallized readily, and the molecular structure of this previously elusive, but crucial intermediate in template-directed multiple addition reactions of 1 was also characterized by means of X-ray analysis. Clearly, the readiness of certain regularly structured and rigid addition products of C 60 (1) to crystallize [30] [31] is a particular asset for the characterization of thermally labile addition products of C 60 . Fig.…”

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confidence: 99%

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The Orthogonal (e,e,e)‐Tris‐Adduct of 9,10‐Dimethylanthracene with C₆₀‐Fullerene: A Hidden Cornerstone of Fullerene Chemistry. Preliminary Communication

Duarte-Ruiz¹,

Wurst²,

Kräutler³

2008

Helvetica Chimica Acta

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Tris(9',10]ethanoanthracene [11',12': 1,9;11'',12'': 16,17;11''',12''': 30,31]) [5,6]fullerene C 60 , the orthogonal (e,e,e)-tris-adduct of C 60 and 9,10-dimethylanthracene, was obtained from [4 þ 2]-cycloaddition (Diels -Alder reaction) at room temperature. The thermally unstable orange red (e,e,e)-tris-adduct was purified by chromatography and was isolated in the form of red monoclinic crystals. Its C 3 -symmetric addition pattern was established spectroscopically. Its structure could be further investigated by single crystal X-ray diffraction. The (e,e,e)-tris-adduct of C 60 and 9,10-dimethylanthracene has earlier been suggested as intermediate and reversibly formed critical component in template directed addition reactions of C 60 . This previously elusive compound has now been isolated and structurally characterized.Introduction. -The discovery of the fullerenes [1] and of an efficient method to produce substantial amounts of these spherical carbon molecules [2] has opened a new era of chemistry [1] [3 -5] and has paved the way to synthetic, spectroscopic, and structural studies [6]. One major goal of these studies concerned the exploration of methods to achieve specific exohedral modifications of the symmetric spherical C- . In other cases, the thermal reversibility was exploited to achieve reversible attachment of fullerenes to solid support [19].As the highly symmetrical C-sphere provided by the [5,6]fullerene 1 represents a unique basis for building up three dimensional molecular structures by multiple exohedral functionalization, particular attention was paid to the problem of regioselectivity in functionalization reactions [7] [8]. The underlying need for regiocontrol has provoked extensive studies on i) the patterns of the inherent reactivity of [5,6]fullerene

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The Orthogonal (e,e,e)‐Tris‐Adduct of 9,10‐Dimethylanthracene with C₆₀‐Fullerene: A Hidden Cornerstone of Fullerene Chemistry. Preliminary Communication

Duarte-Ruiz¹,

Wurst²,

Kräutler³

2008

Helvetica Chimica Acta

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“…The X-ray analysis of crystalline 10 obtained from a related thermolysis experiment indeed indicated a mixture of all four diastereoisomeric bisadducts with different relative orientations of the methyl group of the addend, but the same (antipodal trans-1) position of the addends. [31] The two regioisomeric forms expected for 11 a/11 b (methylgroups syn or anti) of the isomer 11 were indeed indicated in its 1 H NMR spectrum. In solution, the bisadducts 11 and 12 were rather unstable and had a high tendency to thermally loose their anthracene addends and to revert to the monoadducts 6 and 7 and finally to 1.…”

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confidence: 83%

Efficient Preparation of Monoadducts of [60]Fullerene and Anthracenes by Solution Chemistry and Their Thermolytic Decomposition in the Solid State

2001

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The efficient preparation of monoadducts of [60]fullerene and seven anthracenes (anthracene, 1-methylanthracene, 2-methylanthracene, 9-methylanthracene, 9,10-dimethylanthracene, 2,3,6,7-tetramethylanthracene, and 2,6-di-tert-butylanthracene) by cycloaddition in solution is described. The seven mono-adducts of [60]fullerene and the anthracenes were characterized spectroscopically and were obtained in good yields as crystalline solids. The monoadducts of [60]fullerene and anthracene, 1-methylanthracene, 2-methylanthracene and 9,10-dimethylanthracene crystallized directly from the reaction mixture. The thermolytic decomposition at 180 degrees C of the crystalline monoadducts of [60]fullerene and anthracene, 1-methylanthracene, 9-methylanthracene and 9,10-dimethylanthracene all gave rise to the specific formation of a roughly 1:1 mixture of [60]fullerene and the corresponding antipodal bisadducts ("trans-1"-bisadducts) of [60]fullerene and the anthracenes. In contrast, the crystalline monoadducts of [60]fullerene and the anthracene derivatives 2-methylanthracene, 2,3,6,7-tetramethylanthracene and 2,6-di-tert-butylanthracene all decomposed to [60]fullerene and anthracenes (without detectable formation of bisadducts) upon heating in the solid state to temperatures of 180 to 240 degrees C. The formation of the antipodal bisadducts from thermolytic decomposition of crystalline samples of the monoadducts was rationalized by topochemical control.

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“…3 Other good dienophile candidates for reversible [4+2] cycloadditions are fullerenes. [25][26][27][28] Schwenninger et al used the reversibility of the Diels-Alder reaction to synthesize symmetric equatorial tetra adducts of C 60 with labile bound anthracene molecules as directing protection groups. Since its discovery 18 C 60 has shown to undergo a large number of different chemical reactions [19][20][21][22][23][24] where the [4+2] cycloaddition is of particular interest.…”

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confidence: 99%

Molecular self-healing mechanisms between C₆₀-fullerene and anthracene unveiled by Raman and two-dimensional correlation spectroscopy

Geitner

Kötteritzsch

Siegmann

et al. 2016

Phys. Chem. Chem. Phys.

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The self-healing polymer P(LMA-co-MeAMMA) crosslinked with C60-fullerene has been studied by FT-Raman spectroscopy in combination with two-dimensional (2D) correlation analysis and density functional theory calculations. To unveil the molecular changes during the self-healing process mediated by the Diels-Alder equilibrium between 10-methyl-9-anthracenyl groups and C60-fullerene different anthracene-C60-fullerene adducts have been synthesized and characterized by time-, concentration- and temperature-dependent FT-Raman measurements. The self-healing process could be monitored via the C60-fullerene vibrations at 270, 432 and 1469 cm(-1). Furthermore, the detailed analysis of the concentration-dependent FT-Raman spectra point towards the formation of anthracene-C60-fullerene adducts with an unusual high amount of anthracene bound to C60-fullerene in the polymer film, while the 2D correlation analysis of the temperature-dependent Raman spectra suggests a stepwise dissociation of anthracene-C60-fullerene adducts, which are responsible for the self-healing of the polymer.

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The bis-adducts of the [5,6]-fullerene C60 and anthracene

Cited by 49 publications

References 50 publications

The Orthogonal (e,e,e)‐Tris‐Adduct of 9,10‐Dimethylanthracene with C₆₀‐Fullerene: A Hidden Cornerstone of Fullerene Chemistry. Preliminary Communication

The Orthogonal (e,e,e)‐Tris‐Adduct of 9,10‐Dimethylanthracene with C₆₀‐Fullerene: A Hidden Cornerstone of Fullerene Chemistry. Preliminary Communication

Efficient Preparation of Monoadducts of [60]Fullerene and Anthracenes by Solution Chemistry and Their Thermolytic Decomposition in the Solid State

Molecular self-healing mechanisms between C₆₀-fullerene and anthracene unveiled by Raman and two-dimensional correlation spectroscopy

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The bis-adducts of the [5,6]-fullerene C60 and anthracene

Cited by 49 publications

References 50 publications

The Orthogonal (e,e,e)‐Tris‐Adduct of 9,10‐Dimethylanthracene with C60‐Fullerene: A Hidden Cornerstone of Fullerene Chemistry. Preliminary Communication

The Orthogonal (e,e,e)‐Tris‐Adduct of 9,10‐Dimethylanthracene with C60‐Fullerene: A Hidden Cornerstone of Fullerene Chemistry. Preliminary Communication

Efficient Preparation of Monoadducts of [60]Fullerene and Anthracenes by Solution Chemistry and Their Thermolytic Decomposition in the Solid State

Molecular self-healing mechanisms between C60-fullerene and anthracene unveiled by Raman and two-dimensional correlation spectroscopy

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The Orthogonal (e,e,e)‐Tris‐Adduct of 9,10‐Dimethylanthracene with C₆₀‐Fullerene: A Hidden Cornerstone of Fullerene Chemistry. Preliminary Communication

The Orthogonal (e,e,e)‐Tris‐Adduct of 9,10‐Dimethylanthracene with C₆₀‐Fullerene: A Hidden Cornerstone of Fullerene Chemistry. Preliminary Communication

Molecular self-healing mechanisms between C₆₀-fullerene and anthracene unveiled by Raman and two-dimensional correlation spectroscopy