Viologen-Based Rotaxanes from Dibenzo-30-crown-10

Abstract

Three [2]rotaxanes (4, 7, and 12) and one [3]rotaxane (8) were synthesized based on the dibenzo-30-crown-10/viologen binding motif. To the best of our knowledge, these are the first rotaxanes formed from dibenzo-30-crown-10 and viologens. The rotaxanes were all characterized by H NMR,C NMR, and HRMS. An X-ray crystal structure of one of the [2]rotaxanes (7) was obtained. This work demonstrates for the first time that dibenzo-30-crown-10 does form pseudorotaxane complexes with viologens in solution.

A polyrotaxanated covalent organic network based on viologen and cucurbit[7]uril

“…Owing to their rich redox chemistry 18 and their ability to form inclusion complexes with a number of macrocyclic receptors such as crown ethers 21 , calixarenes 22 , cyclodextrins 23 , cucurbiturils 24,25 , viologens, i.e., 4,4′-bipyridinium ions, are among the most studied ionic moieties in supramolecular chemistry [26][27][28] . To date, several viologen-based ICOFs have been synthesized by conventional methods 15,18,29,30 ; however, the products of these usually high-temperature reactions tend to be insoluble, microcrystalline powders with morphologies that are difficult to control and that have a limited range of practical application.…”

[2]Pseudorotaxane‐Based Supramolecular Optical Indicator for the Visual Detection of Cellular Cyanide Excretion

“…The complexation between H and G was first investigated by 1 HNMR spectroscopy in acetone.T he 1 HNMR spectrum ( Figure 2b)ofane quimolar solutiono fH and G in [D 6 ]acetone displayed only one group of resonance peaks, indicating fast exchange complexation on the 1 HNMR timescale. [22] In comparison with free G,t he signals corresponding to protons H a ,H b , and H f of G exhibited upfield shifts (Dd = À0.06, À0.04, À0.04 ppm for H a ,H b ,a nd H f ,r espectively), providing convincing evidencefor the interactions between H and G.Inaddition, protons on H also exhibited chemical shift changes ( Figures 2b,d). The peak related to protonH 1 on the aromatic ring shifted upfieldfrom 6.78 to 6.66 ppm owing to the interactions between H and G.T om easure the binding affinity of the hostguest complexation, 1 HNMR titration experiments werec on-ducteda tr oom temperature in [D 6 ]acetone.…”

“…As the star compounds in host-guest chemistry,t he syntheses of crown ethers proclaimed the birth of supramolecular chemistry. [14][15][16][17][18][19][20][21][22] Crowne ther-based stimuli-responsive hostguests ystemsa re very attractive and have been widely used in variousa reas. [23][24][25][26][27][28] However,c rown ether-based host-guest complexation for the visual detectiono fc yanide anions, especially the detection of cellularc yanidee xcretion, has not been reported yet.…”

“…As the star compounds in host–guest chemistry, the syntheses of crown ethers proclaimed the birth of supramolecular chemistry . Crown ether‐based stimuli‐responsive host–guest systems are very attractive and have been widely used in various areas .…”

“Reverse” pyridyl cryptands as hosts for viologens

“…There is an ongoing quest in host‐guest chemistry to discover new and stronger complexations, higher yielding syntheses of components, and novel molecular recognition motifs [1]. These efforts lead to better synthetic methods, new materials, and opportunities for superior structural control and unusual and useful properties.…”