Diketo[ n ]CPPs as chiral and shape-adaptive fullerene hosts and precursors to DBP[ n ]CPPs
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]CPP, 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 property of diketo[n]CPPs, facilitated by the tunable angle of the diketo unit, enables efficient host-guest interactions with fullerenes. Fluorescence titration revealed similar binding constant for both fullerenes C60 and C70 (5 × 10^4 – 7 × 10^4 M^−1 in toluene), corroborated by DFT calculations that illustrate adaptive changes in nanohoop geometry upon fullerene complexation
Related
- The Effect of a Fullerene Water Suspension on the Growth, Cell Viability, and Membrane Integrity of Escherichia coli B23
- Negative effects of oxygen and halogen species on charge extraction in perovskite solar cells with fullerene electron transport layers
- Pristine isolation of sixfold-symmetric oblate C72 fullerene validating the isolated pentagon rule and the spherical-saturation principle
- Dopant-Controlled Gas Adsorption and Electronic Response in AlN-and BP-Doped Two-Dimensional Fullerene Networks: A DFT and Ab Initio Molecular Dynamics Study
- Topology-Driven Sodium Storage and Conversion in Covalent Fullerene Networks
BibTeX
@article{xiang2026diketo,
title = {{Diketo[ n ]CPPs as chiral and shape-adaptive fullerene hosts and precursors to DBP[ n ]CPPs}},
author = {Xiaoshuang Xiang and Mathias Hermann and Lei Ye and Philipp Seitz and Lilian Estaque and Grégory Pieters and Thomas Drewello and Birgit Esser},
journal = {Chemical Science},
year = {2026},
month = oct,
doi = {10.1039/d5sc05305f},
url = {https://hal.science/hal-05790132v1},
note = {CC BY},
}
RIS
TY - JOUR
TI - Diketo[ n ]CPPs as chiral and shape-adaptive fullerene hosts and precursors to DBP[ n ]CPPs
AU - Xiaoshuang Xiang
AU - Mathias Hermann
AU - Lei Ye
AU - Philipp Seitz
AU - Lilian Estaque
AU - Grégory Pieters
AU - Thomas Drewello
AU - Birgit Esser
PY - 2026
DA - 2026/10/09
JO - Chemical Science
DO - 10.1039/d5sc05305f
UR - https://hal.science/hal-05790132v1
AB - 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]CPP, 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 property of diketo[n]CPPs, facilitated by the tunable angle of the diketo unit, enables efficient host-guest interactions with fullerenes. Fluorescence titration revealed similar binding constant for both fullerenes C60 and C70 (5 × 10^4 – 7 × 10^4 M^−1 in toluene), corroborated by DFT calculations that illustrate adaptive changes in nanohoop geometry upon fullerene complexation
SN - 2041-6520
SN - 2041-6539
ER -