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

Abstract

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.

Exploring fullerene derivatives for optoelectronic applications: synthesis and characterization study

“…Due to the challenges in precisely estimating the solubility of intensely coloured compounds, the solubility of 14 was assessed using UV-Vis spectroscopy as a representative of the other compounds since they only differ in the stereochemistry of the sugar addend. 35 The results indicated that 14 is soluble in toluene at concentrations of 60 mg mL −1 . The significance of this property of furan-fused fullerenes lies in their potential applications and their amenability to processing in material chemistry.…”

“…In a recent paper, we presented the synthesis of furan-fused fullerenes using a simple reaction protocol for oxidative cycloaddition reaction between medium chain β-keto esters and C 60 in the presence of DBU and 2,2,6,6-tetramethylpiperidine-1-oxy (TEMPO) in toluene for 45 minutes at room temperature. 34,35 The resulting procedure was now used to synthesize fullerene-sugar adducts 13 , 14 , and 15 , which were obtained in yields ranging from 49% to 60%.…”