Triptycene-derived calix[6]arenes: synthesis, structure and tubular assemblies in the solid state

Abstract

A couple of novel triptycene-derived calix[6]arenes with fixed conformations were synthesized, and shown to form tubular assemblies with aromatic rings as the walls and phenolic hydroxyl groups situated in the cavities, in the solid state.

Triptycene‐Derived Calix[6]arenes: Synthesis, Structures, and Their Complexation with Fullerenes C60 and C70

“…Synthesis of triptycene‐derived calix[6]arenes : The synthesis of the triptycene‐derived calix[6]arenes 4 and 5 is depicted in Scheme . We previously reported that the diastereomeric triptycene‐derived calix[6]arenes 4 a and 5 a could be conveniently synthesized by one‐pot reaction of the triptycene derivative 1 and p‐tert ‐butylphenol in o ‐dichlorobenzene in the presence of 4‐methylbenzenesulfonic acid 8a. Following the same approach, the calix[6]arenes 4 b and 5 b were synthesized in 17 and 11 % yield, respectively, by the one‐pot reaction of 1 and p ‐phenylphenol.…”

“…We further envisaged that if one or more phenol group(s) in the classical calix[4]arene were to be replaced by appropriate triptycene moieties, a new class of triptycene‐derived calixarenes with larger cavities and fixed conformations would be obtained. Consequently, we synthesized some novel triptycene‐derived calix[6]arenes with fixed conformations and found that they formed tubular assemblies in the solid state 8a. More recently, we also reported a series of triptycene‐derived calix[5]arene derivatives with fixed cone conformations in solution and in the solid state 8b.…”

Synthesis and Reactions of Triptycene‐Derived Bromocalix[5]arenes: Conformational Transformation from Cone to 1,2‐Alternate

“…1,8‐Dimethoxy‐2,7‐dimethyl‐4,5‐dibromotriptycene ( 2 ) was first prepared by treatment of 1 9a with an excess of bromine. Dibromotriptycene 2 was then used as starting material for the synthesis of dibromo‐TDC[5] 8 by following a synthetic strategy similar to that reported before (Scheme ) 9c.…”

Triptycene‐Based Chiral Macrocyclic Hosts for Highly Enantioselective Recognition of Chiral Guests Containing a Trimethylamino Group

“…Triptycene, with its unique three‐dimensional structure, has been proven to be a useful building block for various macrocyclic hosts, including calixarenes and calixarene analogues –. In most cases, however, triptycene has merely been employed as a rigid aromatic scaffold to link the functional blocks, such as oligo(ethylene glycol) chains or other aromatic fragments.…”