A chiral electrochemically responsive molecular universal joint (EMUJ) was synthesized by fusing a macrocyclic pillar[6]arene (P[6]) to a ferrocene-based side ring. A single crystal of an enantiopure EMUJ was successfully obtained, which allowed, for the first time, the definitive correlation between the absolute configuration and the circular dichroism spectrum of a P[6] derivative to be determined. The self-inclusion and self-exclusion conformational change of the EMUJ led to a chiroptical inversion of the P[6] moiety, which could be manipulated by both solvents and changes in temperature. The EMUJ also displayed a unique redox-triggered reversible in/out conformational switching, corresponding to an occupation/voidance switching of the P[6] cavity, respectively. This phenomenon is an unprecedented electrochemical manipulation of the capture and release of guest molecules by supramolecular hosts.

Redox-Triggered Chirality Switching and Guest-Capture/Release with a Pillar[6]arene-Based Molecular Universal Joint.

A novel and facile chiral sensing platform has been designed for electrochemical enantiomer recognition based on the coupling of three-dimensional-graphene with hydroxypropyl-β-cyclodextrin (3D-G/HP-β-CD). The chiral platform synergistically exploits HP-β-CD as a supramolecular chiral recognizer and 3D-G as an electrochemical indicator, to recognize tryptophan (Trp) enantiomers by differential pulse voltammetry (DPV) approach with significantly discernable electrochemical signals. The different host–guest interactions of D- and L-Trp with HP-β-CD reveal high binding affinity to target L-tryptophan for sensing tryptophan isomers. Moreover, we found that the peak currents of the two enantiomers showed a linear response in the concentration range of 0.5–175 μM with low detection limits of 9.6 nM and 38 nM for L- and D-Trp (S/N = 3), respectively, exhibiting remarkable sensitivity, fine reproducibility as well as great stability. This process, which is the initial demonstration of cyclodextrin-functionalized 3D-G for an electrochemical chiral recognition application, provides a new strategy for enantiosensing.

3D graphene/hydroxypropyl-β-cyclodextrin nanocomposite as an electrochemical chiral sensor for the recognition of tryptophan enantiomers

Supramolecular enantiomeric and structural differentiation of amino acid derivatives with achiral pillar[5]arene homologs

Fullerene chemistry has come a long way since 1990, when the first bulk production of C60 was reported. In the past decade, progress in supramolecular chemistry has opened some remarkable and previously unexpected opportunities regarding the selective (multiple) functionalization of fullerenes and their (self)assembly into larger structures and frameworks. The purpose of this review article is to provide a comprehensive overview of these recent developments. We describe how macrocycles and cages that bind strongly to C60 can be used to block undesired addition patterns and thus allow the selective preparation of single-isomer addition products. We also discuss how the emergence of highly shape-persistent macrocycles has opened opportunities for the study of photoactive fullerene dyads and triads as well as the preparation of mechanically interlocked compounds. The preparation of two- or three-dimensional fullerene materials is another research area that has seen remarkable progress over the past few years. Due to the rapidly decreasing price of C60 and C70, we believe that these achievements will translate into all fields where fullerenes have traditionally (third-generation solar cells) and more recently been applied (catalysis, spintronics).

Recent advances in supramolecular fullerene chemistry.

Chirality is one of the basic attributes of nature. Generally, enantiomers exhibit different or even entirely opposite metabolic, toxicological and pharmacological properties in organisms. Hence, chiral recognition is of great importance especially in areas of bioanalysis, pharmaceutics, biomedicines, etc. Cyclodextrins (CDs) are cyclic oligosaccharides with plenty of chiral centers, playing a crucial role in enantiomers discrimination. Due to the unique truncated cone shape structure including a hydrophobic inner cavity and a hydrophilic exterior, CDs are able to recognize optical stereoisomers through host-guest interaction. By far, a board range of analytical techniques has been developed based on CD derivatives for chiral recognition, such as electrochemistry, luminescence, nuclear magnetic resonance (NMR), etc. However, there are still very few reviews focusing on advances in CDs-based enantiomers discrimination techniques. Therefore, we present this review to summarize the recent advances in CDs-based chiral recognition techniques. Both the design strategies and the recognizing mechanisms that transform discriminating process into detectable signals are discussed in details.

Recent advances in cyclodextrins-based chiral-recognizing platforms

Enhanced chiral recognition by γ-cyclodextrin-cucurbit[6]uril-cowheeled [4]pseudorotaxanes.

Fulleropillar[4]arene: The Synthesis and Complexation Properties.

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Enhanced chiral recognition by γ-cyclodextrin-cucurbit[6]uril-cowheeled [4]pseudorotaxanes.

Fulleropillar[4]arene: The Synthesis and Complexation Properties.