Selective Separation of Phenanthrene from Aromatic Isomer Mixtures by a Water-Soluble Azobenzene-Based Macrocycle

Abstract

Selective separation of phenanthrene (PHE) from aromatic isomer mixtures is a big challenge in industry. In this work, a light-responsive water-soluble azobenzene-based macrocycle 1 is synthesized and an aqueous solution of E,E-1 is employed to separate PHE from anthracene via a solid−liquid extraction method under ambient conditions. After five extraction cycles, the average purity for PHE is about 91.1% and macrocycle 1 can be reused at least five times without obvious reduction of separation performance for PHE. This work not only comprises a new and clean way to separate PHE by taking advantage of a macrocyclic host but also promotes the application of host−guest chemistry.

Advances in Chirality Sensing with Macrocyclic Molecules

“…Multiple interactions and even hierarchical chiral structures provide more possibilities for signal amplification. New macrocyclic arenes, such as naphthalene-based macrocycle [67], anthracene-based macrocycle [68], phenanthracene-based macrocycle [69], and azobenzene-based macrocycle [70], have recently emerged with π-conjugated structures, strong luminescence properties, and flexible conformational changes. These new macrocycles provide new potential in chirality-induced CD or CPL detection.…”

Synthesis of Donor‐Acceptor π‐Conjugated Macrocycles by Post‐Functionalization†

“…Organic macrocyclic compounds as one of the most widely utilized host molecules for molecular recognition have attracted great attention. [ 1‐3 ] Various types of macrocycles have been studied to encapsulate different guest molecules by tuning the units of main frameworks and the size of cavities, which is applied in the fields of adsorption, [ 4‐5 ] separation, [ 6‐7 ] sensing, [ 8‐11 ] drug delivery, [ 12‐13 ] and molecular machines. [ 14‐15 ] The macrocyclic molecules can effectively arrange multiple recognition sites together, reducing the negative entropy effect from the orderly arrangement of recognition sites, thereby achieving the purpose of effectively identifying guest molecules or ions.…”

Bottom-Up Solid-State Molecular Assembly via Guest-Induced Intermolecular Interactions

“…Supramolecular macrocyclic receptors can selectively bind guest molecules to form various host–guest assemblies in solution or the solid state via multiple weak intermolecular interactions, such as π–π stacking, hydrogen bonding, charge-transfer interactions, and cation−π interactions. − Considering the analogous dynamic and reversible nature of supramolecular interactions and dynamic combinatorial chemistry, we conjecture that we could manipulate the molecular motion of a disordered system by utilizing noncovalent interactions between macrocyclic hosts and suitable guests to afford crystalline topological structures with high thermodynamic stability such as COFs.…”