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CC BY 4.0 · Organic Materials 2022; 4(02): 7-17
DOI: 10.1055/a-1814-7686
DOI: 10.1055/a-1814-7686
Supramolecular Chemistry
Original Article
Synthesis and C60 Binding of Aza[10]CPP and N-Methylaza[10]CPP
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 transferPublikationsverlauf
Eingereicht: 13. Januar 2022
Angenommen nach Revision: 10. März 2022
Accepted Manuscript online:
01. April 2022
Artikel online veröffentlicht:
04. Mai 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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