Recent advances in the chemistry of cyclotriveratrylene

Abstract

New chemistry of the cyclic molecular host cyclotriveratrylene (CTV) includes applications such as in sensors and separations; in self-organised materials such as gels, liquid crystals, dendritic systems, and self-assembled monolayers; and in metallo-supramolecular chemistry. This tutorial review covers aspects of CTV chemistry interest to supramolecular, coordination and host-guest chemists as well as those interested in self-organised systems.

Self-assembled Cages and Capsules Using Cyclotriveratrylene-type Scaffolds

“…The pyrimidine-functionalized («)-tris- [4-(5- 3+ cages of the same chirality, although it crystallizes as a racemic mixture. The [2]catenane forms in the absence of a template or evident strong structure-directing interactions, which is unusual for a mechanically interlocked assembly. The existence of the {[Ag 3 (L8) 2 ]} 2 6+ [2]catenane in solution is supported by mass spectrometry.…”

“…The [2]catenane forms in the absence of a template or evident strong structure-directing interactions, which is unusual for a mechanically interlocked assembly. The existence of the {[Ag 3 (L8) 2 ]} 2 6+ [2]catenane in solution is supported by mass spectrometry. This is one of the few multiply interlocked catenane-cage compounds that have recently been reported for both metallocages 32,33 and purely organic cages.…”

“…These have a range of potential applications including sensor chemistry, separations, dendrimers, gels, and liquid crystals. 2 This review will focus on capsule and cage architectures based on cyclotriveratrylene scaffolds that have been accessed using labile self-assembly, either through dynamic organic bond formation, hydrogen bonding, or metal-directed assembly. The chemistry of cages and capsules is a highly active area because they possess a large and well-defined internal cavity that can be used to bind guest molecules or ions, with potential for subsequent application as nanoscale reaction vessels and in enzyme-like catalysis.…”

From Zeolite to Host-Guest Nanocomposite Materials

“…These compounds can be synthesised from veratrole alcohol by addition of a suitable acid which can be perchloric acid in methanol or formic acid or sulfuric acid in acetic acid [96]. Fig.…”

Hexasulfanyl analogues of cyclotriveratrylene

“…[1][2][3] CTV itself can complex fullerenes or other globular molecular guests within its hydrophobic cavity. Moreover, other functionalities can be appended onto the CTV scaffold by derivatization of its methoxy groups, allowing organic [2][3][4][5] and metal-organic 2,6,7 cage compounds, frameworks and other supramolecular assemblies 8 based on the CTV moiety to be constructed. Recently, we 9,10 and others 11,12 have extended the chemistry of CTV by preparing thiolated analogues 1 and 2 (Scheme 1).…”