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In this work, we describe the stoichiometrically controlled self-assembly process of tetraurea calix[4]pyrrole 1 with a polar neutral guest, trimethylamine N -oxide or beta-alanine betaine, and methyltrioctylammonium chloride (MTOACl) salt into two supramolecular architectures which differ in morphology and stoichiometry. Whereas an equimolar solution of tetraurea calixpyrrole 1 , polar guest and MTOACl produces a four-particle inclusion assembly, a mixture of the same components in a 2 : 1 : 1 molar ratio induces the formation of a dimeric capsular assembly displaying multiple guests which are orderly co-encapsulated. The influence of other polar guests and ammonium salts on the self-assembly process is also described.

Ordered co-encapsulation of chloride with polar neutral guests in a tetraurea calix[4]pyrrole dimeric capsule