Oxatub[4]arene: a smart macrocyclic receptor with multiple interconvertible cavities

Abstract

We report a smart macrocycle with four interconvertible cavities, which can select the best-fit cavity for a given guest.

Deciphering Noncovalent Interactions Accompanying 7,7,8,8‐Tetracyanoquinodimethane Encapsulation within Biphene[n]arenes: Nucleus‐Independent Chemical Shifts Approach

“…[22] Stoddart et al derived new macrocycles from fused aromatic ring or heteroatoms composed of 1,4-phenylene-bridged bipyridinium linkages to form a box-like architecture or ExBox 4 + , which was explored as a scavenger for an array of polycyclic aromatic hydrocarbons in aqueous or organic media. [23] The incorporation of two biphenylene-bridged 4,4'-bipyridinium extended viologen units into a para-phenylene-based cyclophane led to a new generation of synthetic Ex 2 Box 4 + receptors with remarkable recognition toward p-electron-rich or -deficient hydrocarbons.…”

Desymmetrized Leaning Pillar[6]arene

“…Rapid development of supramolecular chemistry has been heavily dependent on the design and synthesis of precisely defined macrocyclic compounds with specifically tailored host-guest properties.I nt he past five decades,s everal important categories of supramolecular macrocycles,t hat is, crown ethers,c yclodextrins,c alixarenes,c ucurbiturils,a nd pillararenes,have provided awide range of functions as highperformance supramolecular hosts. [1][2][3] More recently,alarge number of new synthetic macrocyclic containers with novel structures and excellent host-guest properties were reported, including calix [4]imidazolium, [4] "Texas-sized" box, [5] Exbox, [6] bambus [6]uril, [7] cyanostar, [8] molecular triangular prisms, [9] oxatub [4]arene, [10] thioether cyclophanes, [11] corona- [5]arenes, [12] janusarene, [13] and others. [14] Thesynthetic accessibility,preorganized structures,facile functionalization methods,and predictable noncovalent interactions enable their applications in host-guest binding, supramolecular self-assembly,m olecular machinery,s timuliresponsive materials,a nd many others.…”

Synthesis, Structure, and Anion Binding Properties of Electron‐Deficient Tetrahomocorona[4]arenes: Shape Selectivity in Anion–π Interactions

“…Tailor-made macrocycles are excellent models to study the non-covalent bond interactions with guests,f acilitating the comprehension of the nature of host-guest chemistry.F unctionalized macrocycles also provide invaluable building units for the construction of sophisticated (supra)molecular architectures,enabling the fabrication of advanced optoelectronic materials,s ensors and molecular machines. [1] As ar esult, an umber of new synthetic macrocyclic hosts [2][3][4][5][6] have been emerging in recent decades,p roviding useful additions to classic and privileged macrocycles. [1,7] Very recently,w eh ave devised corona[n]arenes, [8] an ew type of synthetic macrocycles,w hich are composed of paraarylenes and heteroatoms alternatively in am acrocyclic manner.W ee nvisioned that the combination of various arylene and heteroatom components would generate almost limitless diverse macrocycles.O nt he other hand, rational selection of arylenes of varied sizes and control of the numbers of the arylene and heteroatom building blocks would form coronarenes with cylinder cavities of different shapes and sizes.Most importantly,the electronic interplay between arylenes and heteroatoms would enable the fine regulation of conformations and electronic features of macrocyclic cavities which are pivotal to supramolecular applications.…”