A chiral member of the family of organic hexameric cages

Abstract

A cubic nanocage (O symmetry) that exhibits inherent chirality and has a covalent, rigid skeleton with molecule-sized entrance portals was obtained by means of dynamic covalent chemistry using a reaction between aldehyde-functionalized resorcin[4]arene and hydrazine.

Water-stable hydrazone-linked porous organic cages

“…To date, the largest reported hydrazone-linked organic cage is a [3+3] RC4A-based cage constructed from three tetraformylfunctional RC4As and three tetrahydrazone-functional RC4As, containing an internal cavity with a maximum diameter of 2.12 nm and volume of about 1883 Å 3 calculated by Voidoo. 56 Moreover, the average length of the trigonal window is about 2.0 nm (measured between neighboring bridge carbon of C4RA units), which is large enough to accommodate a molecule with a diameter of 9.51 nm.…”

“…To the best of our knowledge, only four hydrazonelinked organic cage structures are solved by SCXRD, and none of their cavity diameters is more than 2.5 nm. [55][56][57][58] Both indexes are much lower than those of imine-linked cages with numerous crystals characterized by SCXRD and a cavity diameter up to 4.3 nm. 59 Moreover, none of the reported hydrazone-linked organic cages has been explored as porous molecular solids for practical applications.…”

Concentration‐Dependent Self‐Assembly of an Unusually Large Hexameric Hydrogen‐Bonded Molecular Cage

“…The cages are formed using dynamic covalent imine chemistry and feature openings of considerable size ( d ∼8 Å). The approach [13] has been extended towards chiral hydrazone cages by Szumna and co‐workers using resorcinarene derivatives with unfunctionalized phenol groups [14] …”

Efficient ethylene purification by a robust ethane-trapping porous organic cage

“…They possess electron-rich π cavities and eight upper-rim phenolic groups, and have been determined to be effective hosts for inclusion of a variety of guests range from small gases to large organic molecules [44][45][46][47][48] . Notably, their upper rims can be easily functionalized, and this makes them good molecular building blocks for construction of self-assembled cages as well as porous polymers [49][50][51][52][53][54][55] . Very recently, by using pre-designed concave-shaped tetraformylresorcin [4] 56 .…”