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CC BY 4.0 · Organic Materials 2022; 4(02): 7-17
DOI: 10.1055/a-1814-7686
Supramolecular Chemistry
Original Article

Synthesis and C60 Binding of Aza[10]CPP and N-Methylaza[10]CPP

Fabian Schwer
a   Institute of Organic Chemistry, Ulm University, Albert-Einstein-Allee 11, 89081 Ulm, Germany.
,
Simon Zank 
b   Department of Chemistry and Pharmacy, Physical Chemistry I, Friedrich-Alexander Universität Erlangen-Nürnberg, Egerlandstrasse 3, 91058 Erlangen, Germany.
,
Markus Freiberger
b   Department of Chemistry and Pharmacy, Physical Chemistry I, Friedrich-Alexander Universität Erlangen-Nürnberg, Egerlandstrasse 3, 91058 Erlangen, Germany.
,
Ramandeep Kaur
b   Department of Chemistry and Pharmacy, Physical Chemistry I, Friedrich-Alexander Universität Erlangen-Nürnberg, Egerlandstrasse 3, 91058 Erlangen, Germany.
,
Stefan Frühwald
c   Department of Chemistry and Pharmacy, Theoretical Chemistry, Friedrich-Alexander Universität Erlangen-Nürnberg, Egerlandstrasse 3, 91058 Erlangen, Germany.
,
Craig C. Robertson
d   Department of Chemistry, University of Sheffield, Brook Hill, Sheffield S3 7HF, U. K.
,
Andreas Görling
c   Department of Chemistry and Pharmacy, Theoretical Chemistry, Friedrich-Alexander Universität Erlangen-Nürnberg, Egerlandstrasse 3, 91058 Erlangen, Germany.
,
Thomas Drewello 
b   Department of Chemistry and Pharmacy, Physical Chemistry I, Friedrich-Alexander Universität Erlangen-Nürnberg, Egerlandstrasse 3, 91058 Erlangen, Germany.
,
Dirk M. Guldi 
b   Department of Chemistry and Pharmacy, Physical Chemistry I, Friedrich-Alexander Universität Erlangen-Nürnberg, Egerlandstrasse 3, 91058 Erlangen, Germany.
,
Max von Delius 
a   Institute of Organic Chemistry, Ulm University, Albert-Einstein-Allee 11, 89081 Ulm, Germany.
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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.

Key words

curved π-systems - host–guest chemistry - fullerenes - nitrogen doping - photo-induced electron transfer

Supporting Information



Publication History

Received: 13 January 2022

Accepted after revision: 10 March 2022

Accepted Manuscript online:
01 April 2022

Article published online:
04 May 2022

© 2022. The Author(s). This is an open access article published by Thieme under the terms of the Creative Commons Attribution License, permitting unrestricted use, distribution, and reproduction so long as the original work is properly cited. (https://creativecommons.org/licenses/by/4.0/)

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