Novel [2]pseudorotaxanes constructed by self-assembly of bis-urea-functionalized pillar[5]arene and linear alkyl dicarboxylates

Abstract

A bis-urea-functionalized pillar[5]arene has been synthesized and shown to form [2]pseudorotaxanes spontaneously with linear alkyl dicarboxylates in highly polar solvent DMSO, in which the hydrogen bonding interactions between the bis-urea hydrogens and dicarboxylate oxygens play an important role in stabilizing the novel [2]pseudorotaxanes alongside C-Hπ interactions.

Pillar-Shaped Macrocyclic Hosts Pillar[n]arenes: New Key Players for Supramolecular Chemistry

“…106 The monobromide 39 [5] and dibromide 40 [5], which are prepared by cocyclization method (Scheme 15), were converted to monoamine 70 [5] and diamine 71 [5], respectively, by Gabriel synthesis (Scheme 22). 84,107 Mono-72 [5] and diureidopyrimidinone 73 [5] were synthesized from the monoamine 70 [5] and A1/A2 diamine 71 [5], respectively. Reaction between azides and alkynes with copper(I), the copper(I)-catalyzed Huisgen alkyne−azide 1,3-dipolar cycloaddition reaction (CuAAC reaction), is a very efficient and quick reaction.…”

Synthesis of Copillar[5]arenes and Their Host‐Guest Complexation with Two Types of Guests

“…[24][25][26] Importantly, the complexation selectivity of pillararenes towards guest molecules can be tuned by varying the shape and size of the cavity or modifying the substituents on the upper and lower rims. A complete complexation selectivity was found between pillar [5]-and pillar [6]arenes with alkyl bromides due to their different size of cavity. [27] Considering the small size cavity of pillar [5]arene among other analogues, guest molecules have to be carefully selected for hostguest complexation study.…”

“…Pillar[n]arenes, a new type of macrocyclic hosts, para-bridged analogues of calixarenes, have attracted considerable attention owing to their applications in host-guest chemistry, [1][2][3][4] self-assembly chemistry, [5][6][7] material chemistry, [8][9][10][11] photochemistry, [12][13][14] fluorescence chemistry, [15][16][17][18][19][20][21] and biochemistry. [22,23] As pillararenes show high symmetrical and rigid pillar-like structure and have rich electron density, they exhibit excellent host-guest binding properties for a variety of neutral and electron accepting molecules by weak noncovalent interactions (van der Waals, CH-π, cation-π, H-bonding, etc.).…”

A New Cationic Functionalized Pillar[5]arene and Applications for Adsorption of Anionic Dyes

“…Based on their peculiar structure, chemists have explored the dynamic process of threading and de-threading by changing the conditions to tune the host-guest interactions (such as light, [20] temperature, [21] solvent, [22] etc. Due to its pillar-like structure and electron-rich cavity, this promising macrocycle has been used for the construction of host-guest system with neutral, [28] positive [29] or negative [30] guest. [23] Pillar[5]arene, [24] first synthesized by Ogoshi in 2008, is a new member of the macrocyclic family along with crown ether, [25] cucurbituril [26] and calixarene.…”