Synthesis and properties of bis(pyrrolidino)fullerenes bridged by a flexible alkyl-tether

Kop, Tatjana J.; Bjelaković, Mira S.; Milić, Dragana

doi:10.1016/j.tet.2015.05.038

Cited by 6 publications

(10 citation statements)

References 36 publications

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“…2). In addition, observed distinct absorption patterns in the 400-750 nm visible region were similar to those reported for bis(pyrrolidino)fullerenes bridged by alkyl-tether, 20 as well as to other C 60 bisadducts, 24 such conrming the major impact of the fullerene chromophore and addition pattern on the absorption properties.…”

Section: Structure Determinationsupporting

confidence: 82%

“…The addition patterns of bisadduct regioisomers have also been corroborated by the molecular symmetry deduced from their 1 H and 13 C NMR spectra (C s symmetry for cis-1, cis-2, and eq; C 2 symmetry for cis-3). 11d, 20 The expanded 1 H and 13 C NMR spectral regions of all the products 7-14 are presented in Fig. 3 and 4, respectively.…”

Section: Structure Determinationmentioning

confidence: 99%

“…27 In our previous work it has been shown that both addition pattern and the connecting moiety expressed a remarkable inuence on the self-assembling of alkyl tethered bis(pyrrolidino)fullerenes. 20 Therefore, we assume that new fullerene containing bisadducts 7-13, together with dumbbell-like difullerene compound 14 offer the possibility to study the synergistic effects of the polar oxaalkane chain and the fullerene cage on the self-assembly process.…”

Section: Morphologymentioning

confidence: 99%

“…In addition, an inuence of the bridge structure and length on the electrochemical behaviour was examined along the series of compounds with equally positioned, but variously tethered pyrrolidine rings. To that purpose, the electrochemical data of the cis-2 adducts 8 and 9, achieved in ODCB/DCM 2 : 1 mixture at the scan rate 0.7 V s À1 and in the presence of TBAP, were compared to those collected for already known alkyl tethered cis-2 adducts 15-19 20 under the same conditions. Detected distortion of the cyclic voltammograms, with anodic to cathodic half-waves separation higher than 60 mV could be attributed to an attenuated electron transfer and the uncompensated resistance, as it was previously observed both for the reference Fc/Fc + system 30 and fullerene derivatives.…”

Section: Electrochemical Propertiesmentioning

confidence: 99%

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Fulleropyrrolidines derived from dioxa- and trioxaalkyl-tethered diglycines

et al. 2015

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Two different a,u-diglicynes linked by linear polyoxaalkyl chains in the presence of formaldehyde underwent Prato reaction to the fullerene C 60 . The shorter linker templated formation of only cisbisadducts, while the longer one afforded a mixture of four bisadducts (all cis and the equatorial) and difullerene dumbbell compound. Their structures were confirmed by the extensive analysis of the spectral data and molecular symmetry, as well. All compounds expressed an ability to arrange into hierarchically ordered supramolecular aggregates, the form of which depended both on the addition pattern and the spacer structure. The attenuated electron-accepting affinity, examined by cyclic voltammetry was in agreement with diminished delocalization of the p-electronic system. In addition, all compounds exerted a notable radical scavenging activity. † Electronic supplementary information (ESI) available: Experimental section, tabular representation of the UV and the NMR data, the NMR and HRMS spectra, additional SEM images, the CV curves of compounds 3-14, and their HPTLC densitograms. See

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Section: Structure Determinationsupporting

confidence: 82%

Section: Structure Determinationmentioning

confidence: 99%

Section: Morphologymentioning

confidence: 99%

Section: Electrochemical Propertiesmentioning

confidence: 99%

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Fulleropyrrolidines derived from dioxa- and trioxaalkyl-tethered diglycines

et al. 2015

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“…The spherical π system present in the fullerene cages makes UV-Vis spectroscopy a versatile tool for characterization. It has been reported that changes in the UV-Vis spectrum of different fullerene derivatives depend on the number of substituents present in the cage, the type of addition, and the geometry of the adduct (Djojo, et al, 1996;Kop, et al, 2015;Lu, et al, 1996). Moreover, some specific absorption can be used as a fingerprint for the identification of specific substitutions in the fullerene, although the nature of the specific transitions is still unknown.…”

Section: Electronic Characterizationmentioning

confidence: 99%

Síntesis regioespecífica y estudio electroquímico de dos derivados carboxílicos C60 solubles en agua

Villada

Duarte-Ruiz

Chaur

2021

Rev. Acad. Colomb. Cienc. Ex. Fis. Nat.

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We report a new methodology for the synthesis of two highly symmetric equatorial malonate hexaadducts of C60 fullerene. The synthetic methodology is based on a series of protection and deprotection steps that allow the preparation of a fullerene [60] functionalized with six symmetrical positioned malonate addends without using complicated and expensive separation techniques (highperformance liquid chromatography, HPLC) or long reaction times. This methodology allowed us to prepare the carboxylic adducts 6 (equatorial octacarboxylic tetraadduct of C60) and 8 (equatorial dodecacarboxylic hexakisadduct of C60). As far as we now, compound 6 has not yet been reported. We also studied the electronic properties of the main compounds by UV-Vis spectroscopy and cyclic voltammetry (CV). The reported fullerene adducts exhibited several reversible reduction processes whose electron transfers are controlled by diffusion.

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