Dynamic Covalent Formation of Concave Disulfide Macrocycles Mechanically Interlocked with Single-Walled Carbon Nanotubes

Balakrishna B, Menon A, Cao K, Gsänger S, Beil SB, Villalva J, Shyshov O, Martin O, Hirsch A, Meyer B, Kaiser U, Guldi DM, von Delius M (2020)

Publication Type: Journal article

Publication year: 2020

Journal

Angewandte Chemie International Edition Wiley

DOI: 10.1002/anie.202005081

Abstract

The formation of discrete macrocycles wrapped around single-walled carbon nanotubes (SWCNTs) has recently emerged as an appealing strategy to functionalize these carbon nanomaterials and modify their properties. Here, we demonstrate that the reversible disulfide exchange reaction, which proceeds under mild conditions, can install relatively large amounts of mechanically interlocked disulfide macrocycles on the one-dimensional nanotubes. Size-selective functionalization of a mixture of SWCNTs of different diameters were observed, presumably arising from error correction and the presence of relatively rigid, curved π-systems in the key building blocks. A combination of UV/Vis/NIR, Raman, photoluminescence excitation, and transient absorption spectroscopy indicated that the small (6,4)-SWCNTs were predominantly functionalized by the small macrocycles 12, whereas the larger (6,5)-SWCNTs were an ideal match for the larger macrocycles 22. This size selectivity, which was rationalized computationally, could prove useful for the purification of nanotube mixtures, since the disulfide macrocycles can be removed quantitatively under mild reductive conditions.

Authors with CRIS profile

Arjun Menon Lehrstuhl für Physikalische Chemie I Sebastian Gsänger Interdisziplinäres Zentrum für Molekulare Materialien Oliver Martin Lehrstuhl für Organische Chemie II Andreas Hirsch Lehrstuhl für Organische Chemie II Bernd Meyer Professur für Computational Chemistry Dirk Michael Guldi Lehrstuhl für Physikalische Chemie I

Involved external institutions

Universität Ulm DE Germany (DE)

How to cite

APA:

Balakrishna, B., Menon, A., Cao, K., Gsänger, S., Beil, S.B., Villalva, J.,... von Delius, M. (2020). Dynamic Covalent Formation of Concave Disulfide Macrocycles Mechanically Interlocked with Single-Walled Carbon Nanotubes. Angewandte Chemie International Edition. https://dx.doi.org/10.1002/anie.202005081

MLA:

Balakrishna, Bugga, et al. "Dynamic Covalent Formation of Concave Disulfide Macrocycles Mechanically Interlocked with Single-Walled Carbon Nanotubes." Angewandte Chemie International Edition (2020).

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