Terphen[n]arenes and Quaterphen[n]arenes (n=3–6): One‐Pot Synthesis, Self‐Assembly into Supramolecular Gels, and Iodine Capture

Abstract

Herein, two new classes of macrocyclic compounds, terphen[n]arenes (TPns) (n=3–6) and quaterphen[n]arenes (QPns) (n=3–6), were designed and synthesized by a one‐step condensation reaction in relatively high yields. They comprise 2,2′′‐dimethoxy terphenyl and 2,2′′′‐dimethoxy quaterphenyl monomers, respectively, linked by methylene bridges. Given their long and rigid monomers, TPns and QPns have much larger cavities and better self‐assembly properties than classic macrocycles. More interestingly, the cyclic pentamers and hexamers TP5, TP6, QP5, and QP6 formed supramolecular organogels, which were composed of interwoven fibers, nanosheets, or entangled macropore networks formed by multiple face‐to‐face and edge‐to‐face π⋅⋅⋅π stacking interactions. The xerogel materials effectively captured volatile iodine, not only in aqueous media but also in the gaseous state, and could be recycled multiple times without obvious loss in performance.

Influence of Monomers’ Structure on the Assembly and Material Property of Pillar[5]arene‐Based Supramolecular Polymer Gels

“…Up to now, lots of SPGs have been constructed via non‐covalent interactions, [ 4‐6 ] such as supramolecular polymer network gels (SPNGs), [ 7‐11 ] supramolecular polymer organic framework gels (SOFGs), [ 12‐13 ] and other type SPGs. [ 14‐15 ] On the other hand, the inherent dynamic, reversible, and adaptive properties of non‐covalent bond interactions endow SPGs with excellent properties. [ 16‐17 ] Meanwhile, due to their specific structures and function, SPGs have attracted much attention in many fields, such as ions detection, [ 18 ] optical materials, [ 19‐20 ] adsorption and separation, [ 21 ] fluorescence sensors, [ 22‐23 ] cell imaging, [ 24 ] etc .…”

Controlled Self-Assembly Mediated by the Complexation of Calixpyridinium: Diverse Assembled Morphology, Solid-State Fluorescence, and Iodine Capture Capacity

“…34 Recently, Li et al developed a kind of organic xerogels as adsorbents to capture iodine. 35 Herein, the solid organic supramolecular aggregates exhibited an adsorbent ability to iodine in both the aqueous solution and the vapor phase. As far as we know, this kind of adsorbent for iodine was rarely explored previously.…”

Lanthanide-Mediated Cyclodextrin-Based Supramolecular Assembly-Induced Emission Xerogel Films: A Transparent Multicolor Photoluminescent Material

“…26−33 Hence, supramolecular metallic hydrogels based on lanthanide ions, due to their excellent photoluminescence properties, are not only excellent sources for the preparation soft materials but also used in unprecedented applications ranging from luminescence sensing, imaging and data storage. 34,35 Different from traditional soft materials, solid-state supramolecular xerogel films have potential applications in novel adsorbent materials, 36,37 photochromic smart windows, 38−40 and LEDs 41,42 with the advantage of portability and in situ visualization.…”