A CTV Analogue: Arene-Persubstituted Cyclotrixylohydroquinoylene and Its Derivatives

Abstract

A crown-shaped cyclotriveratrylene (CTV) analogue with persubstituted arene unitsnamely, cyclotrixylohydroquinoylene (CTX)was synthesized from tetrasubstituted o-xylohydroquinone. Importantly, a series of CTX derivatives were prepared by introducing second bridged methylene, phenylphosphine oxide, and dimethylsilyl at the middle rim, referred to as CTX­[CH 2 ], CTX­[P­(O)­Ph], and CTX­[SiMe 2 ], respectively, with the completely locked crown conformation, leading to the formation of unique C3-symmetric Chinese censer-shaped pocket structures. In addition, the water-soluble CTX­[CH 2 ] derivative (WCTX­[CH 2 ]) was synthesized from CTX­[CH 2 ] by simple oxidation reaction with the modification at the upper rim, and its host–guest interaction with methyl viologen in water was investigated.

Self‐Assembled Cyclotriguaiacyclene‐Integrated Supramolecular Systems for Liquid Crystal and Self‐Assembly Behavior

“…The observed texture pattern of the columnar hexagonal phase is further correlated with the self-organized molecular pattern, as confirmed by XRD study. [26] All four compounds exhibited a higher temperature range of mesophase and thermal stability, persisting up to 19.0 °C during the cooling cycle (CTGF 4 ). On the other hand, we observed that increasing the flexibility of the side-alkyl spacer can impact the crystallinity of the compounds.…”

“…Importantly, the previous study confirmed the use of fluorescein as a linker unit supports the formation of columnar hexagonal phase with higher temperature range of mesophase and light-emitting properties. [26] All four symmetrical tri-substituted CTG-based compounds adopted a crown conformation and displayed a columnar hexagonal type mesophase. The liquid crystalline phase is exhibited under both heating and cooling conditions.…”

Effective Iodine Capture Behavior by a Censer‐shaped Macrocycle in Vapor Phase and Aqueous Solution

“…CTX[P(O)Ph] was synthesized in our previous work in just two steps with high thermal stability. [11] Despite the low surface area, the CTX[P(O)Ph] powder exhibited high performance for both vapor iodine adsorption (0.76 g/g) and aqueous iodine adsorption. In addition, the adsorbent could be regenerated by heating under vacuum and the good reusability was achieved.…”

“…We supposed the iodine could locate inside or outside the cavity of CTX[P(O)Ph] because the benzene rings and P=O moieties could provide extra noncovalent binding sites for iodine molecules. CTX[P(O)Ph] was synthesized in our previous work in just two steps with high thermal stability [11] . Despite the low surface area, the CTX[P(O)Ph] powder exhibited high performance for both vapor iodine adsorption (0.76 g/g) and aqueous iodine adsorption.…”

The Preparation of a Water‐Soluble Phospholate‐Based Macrocycle for Constructing Artificial Light‐Harvesting Systems

“…CTX then could be bridged with methylene groups at its middle rim and then was successfully oxidized to obtain the water-soluble carboxylate-based macrocycle WCTX[CH 2 ]. [18] However, the overall low yield limits its further application, and it is of great significance to construct a phospholate-based water-soluble macrocycle, because it is well known that phosphoric acids and their salts are more biocompatible in biology system. [19] Therefore, herein, biocompatible water-soluble phospholate-based CTX (WPCTX) was prepared by connecting the adjacent hydroxyl groups with phosphoric acid at its middle rim of CTX just in two steps with satisfying yield (Figure 1).…”