Supramolecular Receptor Design: Anion‐Triggered Binding of C₆₀

Abstract

Self-assembled structures are widespread in nature and are a key feature of many biological small-molecule recognition motifs. Not surprisingly, therefore, considerable effort has been devoted to developing synthetic self-assembled receptor systems, multicomponent molecular hosts that are able to[*] Dr.

Wraparound Hosts for Fullerenes: Tailored Macrocycles and Cages

“…The first example was described by Sessler, Jeppesen, and co-workers with derivative 14, which results from the fusion of four tetrathiafulvalene units to a calix [4]pyrrole scaffold ( Figure 6). [26] Compound 14 mainly exists in the 1,3-alternate conformation in solution and interacts with C 60 only very weakly. Yet, thanks to the affinity of calix [4]pyrroles for chloride anion, it is possible to switch this molecule to its cone conformation, which affords the deep and electron-rich cavity 14·Cl À (Scheme 1).…”

Fullerene C60 Architectures in Materials Science

“…The first pyrrole-based moiety able to interact with C 60 through π-π interactions was described by Sessler et al 113 and consisted of a calix [4]pyrrole scaffold fused with four units of TTF ( Figure 2.11b). This molecule interacted with C 60 very weakly in its open form, but is able to switch in a cone conformation after the addition of Cl − ions, forming an electron-rich deep cavity defined by the TTF arms.…”

Calix[4]pyrroles Bearing Pyrene-pickets at Diametrical Meso-positions with Amide Linkage

“…The organic layer was dried (Na 2 SO 4 ) and the solvent was removed in vacuo. The resulting yellow solid was purified by column chromatography on silica (CH2Cl2 /EtOAc = 4/1) to afford (11). Yield 0.033 g (48%); …”

“…Various modified calix [4]pyrroles have been designed and synthesized for improved recognition properties. [7][8][9][10][11][12][13] Among them, calix [4]pyrroles bearing diametrical strap on one side of the macrocycle (A) have attracted attention due to their superior binding properties. [14][15][16][17][18] In contrast to most other calixpyrrole derivatives, these systems allow for a pre-organization of the binding domain, a feature that has allowed for a fine-tuning of their selectivity and affinity.…”