Issue 47, 2022

Modular synthesis, host–guest complexation and solvation-controlled relaxation of nanohoops with donor–acceptor structures

Abstract

Carbon nanohoops with donor–acceptor (D–A) structures are attractive electronic materials and biological fluorophores, but their synthesis is usually challenging. Moreover, the preparation of D–A nanohoop fluorophores exhibiting high fluorescence quantum yields beyond 500 nm remains a key challenge. This study presents a modular synthetic approach based on an efficient metal-free cyclocondensation reaction that readily produced nine congeners with D–A or donor–acceptor–donor′ (D–A–D′) structures, one of which is water-soluble. The tailored molecular design of nanohoops enabled a systematic and detailed study of their host–guest complexation with fullerene, optical properties, and charge transfer (CT) dynamics using X-ray crystallography, fluorescence titration, steady and ultrafast transient absorption spectroscopy, and theoretical calculations. The findings revealed intriguing physical properties associated with D–A motifs, such as tight binding with fullerene, moderate fluorescence quantum yields (37–67%) beyond 540 nm, and unique solvation-controlled CT relaxation of D–A–D′ nanohoops, where two CT states (D–A and A–D′) can be effectively tuned by solvation, resulting in dramatically changed relaxation pathways in different solvents.

Graphical abstract: Modular synthesis, host–guest complexation and solvation-controlled relaxation of nanohoops with donor–acceptor structures

Supplementary files

Article information

Article type
Edge Article
Submitted
20 10 2022
Accepted
07 11 2022
First published
10 11 2022
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2022,13, 14080-14089

Modular synthesis, host–guest complexation and solvation-controlled relaxation of nanohoops with donor–acceptor structures

H. Deng, Z. Guo, Y. Wang, K. Li, Q. Zhou, C. Ge, Z. Xu, S. Sato, X. Ma and Z. Sun, Chem. Sci., 2022, 13, 14080 DOI: 10.1039/D2SC05804A

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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