Sugar‐Bridged Fullerene Dumbbells and Their Interaction with the [10]Cycloparaphenylene Nanoring

• Published in: Chemistry : a European journal Vol. 29; no. 44; pp. e202301061 - n/a
• Main Authors: Jakšić, Jovana, Solymosi, Iris, Hirsch, Andreas, Pérez‐Ojeda, M. Eugenia, Mitrović, Aleksandra, Maslak, Veselin
• Format: Journal Article
• Language: English
• Published: Germany Wiley Subscription Services, Inc 04-08-2023
• Subjects: Binding; Calorimetry; Chemistry; Cyclopropane; dumbbells; Electrochemical analysis; Electrochemistry; Electron affinity; Energy conversion; Fullerenes; isomannides; isosorbides; NMR; Nuclear magnetic resonance; Polymers; pseudorotaxanes; Solar energy; Solar energy conversion; Stoichiometry; Strong interactions (field theory); Titration; Titration calorimetry; dumbbells; fullerenes; isomannides; isosorbides; pseudorotaxanes
• ISSN: 0947-6539; 1521-3765
• DOI: 10.1002/chem.202301061

The synthesis and characterization of four dumbbell‐shaped fullerene molecules connected by isosorbide and isomannide moieties is presented. Additionally, their electrochemical behavior and their ability to form complexes with [10]cycloparaphenylene ([10]CPP) were investigated. The cyclic voltammetry (CV) results of the fullerene dumbbells demonstrate a high electron affinity, indicating their strong interaction with electron‐donating counterparts such as carbon nanorings, which possess complementary charge and shape properties. To study the thermodynamic and kinetic parameters of complexation, isothermal titration calorimetry (ITC) was employed. NMR titration experiments provided further insights into the binding stoichiometries. Two distinct approaches were utilized to create bridged structures: one based on cyclopropane and the other based on furan. Regardless of the type of linker used, all derivatives formed conventional 2 : 1 complexes denoted as [10]CPP2⊃C60derivative. However, the methano‐dumbbell molecules exhibited distinct binding behavior, resulting in the formation of mono‐ and bis‐pseudorotaxanes, as well as oligomers (polymers). The formation of linear polymers holds significant potential for applications in solar energy conversion processes.
Novel sugar‐bridged fullerene dumbbells were synthesized and fully characterized. Methano‐ and furan‐fused C60 interacted with [10]CPP, an electron‐donating nanoring, to form bis‐pseudorotaxanes. Interestingly, the methano‐dumbbell molecules showed a different binding behaviour as mono‐, bis‐pseudorotaxanes as well as oligomers (polymers) were detected.