Synthesis, Electrochemistry, and Hierarchical Self‐Organization of Fulleropyrrolidine–Phthalimide Dyads

Abstract

A series of novel fulleropyrrolidine–phthalimide dyads was synthesized and their electrochemical and self‐assembly properties were investigated. Efficient synthesis of acceptor–acceptor dyads was performed under microwave irradiation. Fine‐tuning of the second redox potentials in the dyads was achieved by varying the length of the aliphatic spacer (C2 to C12) between the fulleropyrrolidine and phthalimide moieties. Shape‐shifting and supramolecular polymorphism were observed for these compounds during self‐assembly.

Efficient one-step synthesis of 4-amino substituted phthalimides and evaluation of their potential as fluorescent probes

“…Good to excellent yields were obtained when diethylamine, morpholine, and piperidine were introduced by using the corresponding amines ( Table 2, entries 2-4). An N-benzylmethylamine, a substituted piperidine, and a Cbz protected piperazine were also well tolerated and gave phthalimides 6, 7 and 8 in 92%, 87% and 72% yields respectively (Table 2, entries [6][7][8]. This proved to be a more effective procedure to introduce the dimethylamino substituent as compared to the use of dimethylamine HCl salt in combination with a base, which resulted in lower yields and more complicated purifications.…”

Synthesis, crystal structure, self-assembly of C60 derivatives bearing rigid pyridine substituents

“…Moreover, the introduced substitutes onto fullerene cage play a vital role in self-assembly process because they provide a weak intermolecular force such as van der Waals forces, in addition to conventional strong p-p interactions between carbon cages. [20][21][22][23][24][25][26] To the best of our knowledge, among fullerene derivatives used for self-assembly, the attached substitutes mainly focus on long alkyl-chains or short aromatic moiety. 23,[26][27][28] In contrast, long alkyl chains on fullerene cage facilitating to improve the solubility of fullerene derivatives, have a side-effect of reducing electronic activity of fullerene.…”

“…[20][21][22][23][24][25][26] To the best of our knowledge, among fullerene derivatives used for self-assembly, the attached substitutes mainly focus on long alkyl-chains or short aromatic moiety. 23,[26][27][28] In contrast, long alkyl chains on fullerene cage facilitating to improve the solubility of fullerene derivatives, have a side-effect of reducing electronic activity of fullerene. The short aromatic moiety containing pyridine groups, 23 benzoate 28 and azo chromophore, 29 although results in the lower solubility in organic solvents, still enables fullerene derivatives to retain most electronic activity of fullerenes.…”

Efficient Synthesis of 2‐Substituted Phthalimides from Phthalic Acids in One Step

“…[1][2][3] In addition, phthalimides have also successfully been used as key components in materials and polymers, [4][5][6][7] as catalysts, [8,9] and as fluorescent probes. [1][2][3] In addition, phthalimides have also successfully been used as key components in materials and polymers, [4][5][6][7] as catalysts, [8,9] and as fluorescent probes.…”

“…The phthalimide core structure is found in commercial drugs and in a wide range of precursors for different biological targets. [1][2][3] In addition, phthalimides have also successfully been used as key components in materials and polymers, [4][5][6][7] as catalysts, [8,9] and as fluorescent probes. [10][11][12] Because of this great interest in phthalimides, the development of convenient, economic, and general synthetic procedures to generate substituted phthalimides directly from phthalic acids would be valuable.…”