Synthesis and C 60Binding of Aza[10]CPP and N -Methylaza[10]CPP

Schwer F, Zank S, Freiberger M, Kaur R, Frühwald S, Robertson CC, Görling A, Drewello T, Guldi DM, Von Delius M (2022)

Publication Type: Journal article

Publication year: 2022

Journal

Book Volume: 4

Pages Range: 7-17

Journal Issue: 2

DOI: 10.1055/a-1814-7686

Abstract

Within the growing family of strained carbon nanohoops and nanobelts, [10]CPP arguably offers the best compromise between synthetic accessibility and strong binding affinity for C60. In this work, we report the synthesis of two nitrogen-containing analogues of [10]CPP and we systematically compare the structure, optoelectronic properties and C60 binding affinities of this small set of structurally similar macrocycles. While Aza[10]CPP outcompetes the parent compound by approximately one order of magnitude with respect to C60 binding, we found that the reverse was true for the methylaza analogue. Transient absorption studies showed that photo-induced electron transfer occurred readily from [10]CPP and its aza-analogue to an encapsulated C60 guest. Formation of a charge-separated complex was not observed however for the N-methylated derivative. These insights will prove useful for further applications of strained nanohoops in supramolecular chemistry and organic electronics.

Authors with CRIS profile

Involved external institutions

Universität Ulm Germany (DE) University of Sheffield United Kingdom (GB)

How to cite

APA:

Schwer, F., Zank, S., Freiberger, M., Kaur, R., Frühwald, S., Robertson, C.C.,... Von Delius, M. (2022). Synthesis and C 60Binding of Aza[10]CPP and N -Methylaza[10]CPP. Organic Materials, 4(2), 7-17. https://doi.org/10.1055/a-1814-7686

MLA:

Schwer, Fabian, et al. "Synthesis and C 60Binding of Aza[10]CPP and N -Methylaza[10]CPP." Organic Materials 4.2 (2022): 7-17.

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