Diketo[n]CPPs as chiral and shape-adaptive fullerene hosts and precursors to DBP[n]CPPs

Xiang X, Hermann M, Ye L, Seitz P, Estaque L, Pieters G, Drewello T, Esser B (2026)

Publication Type: Journal article

Publication year: 2026

Journal

Chemical Science Royal Society of Chemistry

DOI: 10.1039/d5sc05305f

Abstract

Conjugated nanohoops, such as [n]cycloparaphenylenes ([n]CPPs) and derivatives, exhibit unique structural and optoelectronic properties, making them promising candidates for applications in optoelectronic materials, and as hosts for supramolecular chemistry. Using π-systems unsymmetric to rotation or incorporating chiral units can furnish chiral nanohoops. We herein present the synthesis and characterization of diketo[8]- and diketo[9]CPPs, along with their corresponding dibenzo[a,e]pentalene (DBP) derivatives, DBP[8]- and DBP[9]CPP. Due to the central chirality of the diketone-units, these nanohoops are chiral without the possibility of racemization through rotation and show distinct chiroptical properties. The diketo[n]CPPs possess high fluorescence quantum yields of 87% (n = 8) and 92% (n = 9). The shape-adaptive properties of diketo[n]CPPs, facilitated by the tunable kink angle of the diketo unit, enable efficient host–guest interactions with fullerenes. Fluorescence titration revealed a similar binding constant for both fullerenes C60 and C70 (5 × 104 to 7 × 104 M−1 in toluene), corroborated by DFT calculations that illustrate adaptive changes in nanohoop geometry upon fullerene complexation. ESI-MS is employed to generate ionized [1 : 1] host–guest complexes of diketo[9]CPP and DBP[9]CPP with C60 and C70 as guests. The relative stabilities of these complexes are evaluated in energy-resolved collision experiments.

Authors with CRIS profile

Lei Ye Lehrstuhl für Physikalische Chemie I Thomas Drewello Professur für Physikalische Chemie

Involved external institutions

Universität Ulm DE Germany (DE) Université Paris-Saclay FR France (FR)

How to cite

APA:

Xiang, X., Hermann, M., Ye, L., Seitz, P., Estaque, L., Pieters, G.,... Esser, B. (2026). Diketo[n]CPPs as chiral and shape-adaptive fullerene hosts and precursors to DBP[n]CPPs. Chemical Science. https://doi.org/10.1039/d5sc05305f

MLA:

Xiang, Xiaoshuang, et al. "Diketo[n]CPPs as chiral and shape-adaptive fullerene hosts and precursors to DBP[n]CPPs." Chemical Science (2026).

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