Fulleropyrrolidines with orthogonally flexible substituents – Synthesis and electrochemical properties Scientific paper

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Published: Nov 22, 2021
Updated: 22.11.2021
DOI: https://doi.org/10.2298/JSC210708069J
Keywords:
fullerene cyclic voltammetry substituents flexibility

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Dragana Jovanović
University of Belgrade – Faculty of Chemistry, Studentski trg 12-16, 11158, Belgrade, Serbia
https://orcid.org/0000-0001-6518-2368
Jovana Stanojković
University of Belgrade – Faculty of Chemistry, Studentski trg 12-16, 11158, Belgrade, Serbia
https://orcid.org/0000-0001-8602-6153
Dženeta Halilović
University of Belgrade – Faculty of Chemistry, Studentski trg 12-16, 11158, Belgrade, Serbia
https://orcid.org/0000-0002-4617-1898
Rejhana Kolašinac
University of Belgrade – Faculty of Chemistry, Studentski trg 12-16, 11158, Belgrade, Serbia
https://orcid.org/0000-0001-6759-1288
Tatjana Kop
University of Belgrade – Institute of Chemistry, Technology and Metallurgy, Department of Chemistry, Njegoševa 12, 11000, Belgrade, Republic of Serbia
https://orcid.org/0000-0002-6078-2804
Mira Bjelaković
University of Belgrade – Institute of Chemistry, Technology and Metallurgy, Department of Chemistry, Njegoševa 12, 11000, Belgrade, Republic of Serbia
https://orcid.org/0000-0003-1679-7184
Dragana Milić
University od Belgrade - Faculty on Chemistry, Studentski trg 12-16, 11158 Belgrade, Serbia
https://orcid.org/0000-0002-5713-8815

Abstract

A large series of disubstituted fulleropyrrolidines was synthesized and analyzed by cyclic voltammetry. The three main groups of target com­pounds differ by a flexible N-chain, while their further diversity was achieved by the introduction of various rigid, aryl substituents at the pyrrolidine carbon. Some dialkyl analogues were also designed for comparison, A standard [3+2]-cycloaddition of in situ generated azomethine ylides to C60 afforded a variety of disubstituted fulleropyrrolidines. Furthermore, a set of dumbbell-shaped di(fulleropyrrolidine) derivatives containing rigid fumaryl or isophthaloyl diamide platform was prepared with the aim of investigating a long-range effect of the second fulleropyrrolidine moiety on their electrochemical pro­perties. All compounds were fully characterized by comparative analysis of spectral data, while examination of electrochemical properties was performed on representative samples, distinguished by main structural subunits. All com­pounds expressed quite similar electron-accepting ability, lower than C60, but higher in comparison to structurally similar N-methylfulleropyrrolidine.

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How to Cite
[1]
D. Jovanović, “Fulleropyrrolidines with orthogonally flexible substituents – Synthesis and electrochemical properties: Scientific paper”, J. Serb. Chem. Soc., vol. 86, no. 11, pp. 1023–1037, Nov. 2021.
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Vol. 86 No. 11 (2021)
Section
Organic Chemistry
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