Synthesis of a Pillar[5]arene‐Based Heteroditopic Host and Its Complexation with n‐Octyltriethylammonium Salts

A new pillar[5]arene-based heteroditopic receptor containing a urea anion recognition site was designed and made. It was demonstrated that the introduction of the urea group remarkably promoted the binding affinity to n-octyltriethylammonium salts with different counterions in chloroform, as the corresponding monotopic host, 1,4-dimethoxypillar[5]arene, showed weak complexation with these guests. The important role of the urea unit was investigated and it was shown that the urea group and the macrocyclic unit not only provided positioned binding sites for the guests but also acted cooperatively in binding these guests.

[1]  Feihe Huang,et al.  Formation of a pillar[5]arene-based [3]pseudorotaxane in solution and in the solid state. , 2013, Chemical communications.

[2]  Xiao‐Yu Hu,et al.  Improved recognition of alkylammonium salts by ion pair recognition based on a novel heteroditopic pillar[5]arene receptor , 2012 .

[3]  Feihe Huang,et al.  Pillar[6]arene/paraquat molecular recognition in water: high binding strength, pH-responsiveness, and application in controllable self-assembly, controlled release, and treatment of paraquat poisoning. , 2012, Journal of the American Chemical Society.

[4]  Feihe Huang,et al.  Novel [2]rotaxanes based on the recognition of pillar[5]arenes to an alkane functionalized with triazole moieties , 2012 .

[5]  Xiao‐Yu Hu,et al.  Pillar[5]arene-based supramolecular polypseudorotaxanes constructed from quadruple hydrogen bonding , 2012 .

[6]  Feihe Huang,et al.  Cavity‐Extended Pillar[5]arenes: Syntheses and Host–Guest Complexation with Paraquat and Bispyridinium Derivatives , 2012 .

[7]  Jianzhuang Chen,et al.  An amphiphilic pillar[5]arene: synthesis, controllable self-assembly in water, and application in calcein release and TNT adsorption. , 2012, Journal of the American Chemical Society.

[8]  Feihe Huang,et al.  Syntheses of a pillar[4]arene[1]quinone and a difunctionalized pillar[5]arene by partial oxidation. , 2012, Chemical communications.

[9]  A. M. Brouwer,et al.  Excited-state proton transfer and ion pair formation in a Cinchona organocatalyst. , 2012, Physical chemistry chemical physics : PCCP.

[10]  Feihe Huang,et al.  A solvent-driven molecular spring , 2012 .

[11]  Feihe Huang,et al.  A water-soluble pillar[6]arene: synthesis, host-guest chemistry, and its application in dispersion of multiwalled carbon nanotubes in water. , 2012, Journal of the American Chemical Society.

[12]  张明明,et al.  1,4-双正丙氧基柱[7]芳烃的合成及主客体化学 , 2012 .

[13]  Feihe Huang,et al.  Preparation of two new [2]rotaxanes based on the pillar[5]arene/alkane recognition motif , 2012 .

[14]  Jiuming He,et al.  A new water-soluble pillar[5]arene: synthesis and application in the preparation of gold nanoparticles. , 2012, Chemical communications.

[15]  P. Beer,et al.  Heteroditope Rezeptoren zur Ionenpaarerkennung , 2012 .

[16]  Jun-Li Hou,et al.  Single-molecular artificial transmembrane water channels. , 2012, Journal of the American Chemical Society.

[17]  Feihe Huang,et al.  Pillar[6]arene-based photoresponsive host-guest complexation. , 2012, Journal of the American Chemical Society.

[18]  Yong Yang,et al.  Pillararenes, a new class of macrocycles for supramolecular chemistry. , 2012, Accounts of chemical research.

[19]  Yajie Zhang,et al.  Novel self-assembled dynamic [2]catenanes interlocked by the quadruple hydrogen bonding ureidopyrimidinone motif , 2012 .

[20]  Feihe Huang,et al.  Complexation between pillar[5]arenes and a secondary ammonium salt. , 2012, Organic letters.

[21]  Feihe Huang,et al.  per-Hydroxylated pillar[6]arene: synthesis, X-ray crystal structure, and host-guest complexation. , 2012, Organic letters.

[22]  Zhenxia Chen,et al.  Highly effective binding of neutral dinitriles by simple pillar[5]arenes. , 2012, Chemical communications.

[23]  Feihe Huang,et al.  A non-symmetric pillar[5]arene-based selective anion receptor for fluoride. , 2012, Chemical communications.

[24]  Bo Zheng,et al.  Supramolecular polymers constructed by crown ether-based molecular recognition. , 2012, Chemical Society reviews.

[25]  K. Sharma,et al.  Pillar[5]arenes: fascinating cyclophanes with a bright future. , 2012, Chemical Society reviews.

[26]  Jiuming He,et al.  A cationic water-soluble pillar[5]arene: synthesis and host-guest complexation with sodium 1-octanesulfonate. , 2011, Chemical communications.

[27]  Y. Yu,et al.  Novel neutral guest recognition and interpenetrated complex formation from pillar[5]arenes. , 2011, Chemical communications.

[28]  Y. Yu,et al.  Complexation of 1,4-bis(pyridinium)butanes by negatively charged carboxylatopillar[5]arene. , 2011, The Journal of organic chemistry.

[29]  Feihe Huang,et al.  Preparation of Pillar[n]arenes by Cyclooligomerization of 2,5‐Dialkoxybenzyl Alcohols or 2,5‐Dialkoxybenzyl Bromides , 2011 .

[30]  Feihe Huang,et al.  Synthesis of a pillar[5]arene dimer by co-oligomerization and its complexation with n-octyltrimethyl ammonium hexafluorophosphate , 2011 .

[31]  Feihe Huang,et al.  Formation of a cyclic dimer containing two mirror image monomers in the solid state controlled by van der Waals forces. , 2011, Organic letters.

[32]  J. Chambron,et al.  Supramolecular chemical sensors based on pyrene monomer-excimer dual luminescence. , 2011, Chemistry, an Asian journal.

[33]  Y. Yu,et al.  Pillar[5]arene decaamine: synthesis, encapsulation of very long linear diacids and formation of ion pair-stopped [2]rotaxanes. , 2011, Chemical communications.

[34]  J. F. Stoddart,et al.  Monofunctionalized pillar[5]arene as a host for alkanediamines. , 2011, Journal of the American Chemical Society.

[35]  J. Steed Supramolecular gel chemistry: developments over the last decade. , 2011, Chemical communications.

[36]  Feihe Huang,et al.  Four constitutional isomers of BMpillar[5]arene: synthesis, crystal structures and complexation with n-octyltrimethyl ammonium hexafluorophosphate. , 2011, Chemical communications.

[37]  Shin-ichi Kondo,et al.  Anion recognition by 2,2′-binaphthalene derivatives bearing urea and thiourea groups at 8- and 8′-positions by UV–vis and fluorescence spectroscopies , 2011 .

[38]  Feihe Huang,et al.  Improved Pseudorotaxane and Catenane Formation from a Derivative of Bis(m‐phenylene)‐32‐crown‐10 , 2010 .

[39]  Y. Yu,et al.  Self-assembly of [2]pseudorotaxanes based on pillar[5]arene and bis(imidazolium) cations. , 2010, Chemical communications.

[40]  G. Clever,et al.  A pH switchable pseudorotaxane based on a metal cage and a bis-anionic thread. , 2010, Chemistry.

[41]  Feihe Huang,et al.  Improved and Controlled Complexation of Paraquat Derivatives by the Formation of a Bis(m‐phenylene)‐26‐Crown‐8‐Based Lariat Ether , 2010 .

[42]  Jonathan W. Steed,et al.  Anion-tuned supramolecular gels: a natural evolution from urea supramolecular chemistry. , 2010, Chemical Society reviews.

[43]  Philip A. Gale Anion receptor chemistry: highlights from 2008 and 2009. , 2010, Chemical Society reviews.

[44]  Jonathan L Sessler,et al.  Ion pair receptors. , 2010, Chemical Society reviews.

[45]  Feihe Huang,et al.  DIBPillar[n]arenes (n = 5, 6): syntheses, X-ray crystal structures, and complexation with n-octyltriethyl ammonium hexafluorophosphate. , 2010, Organic letters.

[46]  Jonathan W Steed,et al.  Metal- and anion-binding supramolecular gels. , 2010, Chemical reviews.

[47]  L. Delmau,et al.  A calix[4]arene strapped calix[4]pyrrole: an ion-pair receptor displaying three different cesium cation recognition modes. , 2010, Journal of the American Chemical Society.

[48]  Chunju Li,et al.  Complex interactions of pillar[5]arene with paraquats and bis(pyridinium) derivatives. , 2010, Organic & biomolecular chemistry.

[49]  S. Teat,et al.  Dual selectivity expressed in [2 + 2 + 1] dynamic clipping of unsymmetrical [2]catenanes. , 2010, Organic letters.

[50]  I. Jabin,et al.  Acid-base controllable recognition properties of a highly versatile calix[6]crypturea. , 2010, Chemistry.

[51]  H. Meier,et al.  Eine leichte und effiziente Herstellung von Pillararenen und einem Pillarchinon , 2009 .

[52]  P. Kluson,et al.  Quaternary ammonium salts ionic liquids for immobilization of chiral Ru-BINAP complexes in asymmetric hydrogenation of β-ketoesters , 2009 .

[53]  Feihe Huang,et al.  Anion-controlled ion-pair recognition of paraquat by a bis(m-phenylene)-32-crown-10 derivative heteroditopic host. , 2009, The Journal of organic chemistry.

[54]  Feihe Huang,et al.  Improved complexation between dibenzo-24-crown-8 derivatives and dibenzylammonium salts by ion-pair recognition , 2008 .

[55]  V. Lynch,et al.  Crown-6-calix[4]arene-capped calix[4]pyrrole: an ion-pair receptor for solvent-separated CsF ions. , 2008, Journal of the American Chemical Society.

[56]  Yoshiaki Nakamoto,et al.  para-Bridged symmetrical pillar[5]arenes: their Lewis acid catalyzed synthesis and host-guest property. , 2008, Journal of the American Chemical Society.

[57]  Sérgio M. Santos,et al.  Cooperative AND ion-pair recognition by heteroditopic calix[4]diquinone receptors. , 2008, Chemistry.

[58]  I. Jabin,et al.  Synthesis and study of calix[6]cryptamides: A new class of heteroditopic receptors that display versatile host-guest properties toward neutral species and organic associated ion-pair salts. , 2008, Chemistry.

[59]  R. Custelcean,et al.  Crystal engineering with urea and thiourea hydrogen-bonding groups. , 2008, Chemical communications.

[60]  J. Steed,et al.  Simultaneous anion and cation binding by a simple polymer-bound ureidopyridyl ligand. , 2006, Chemical communications.

[61]  Philip A. Gale,et al.  Structural and molecular recognition studies with acyclic anion receptors. , 2006, Accounts of chemical research.

[62]  Bradley D. Smith,et al.  Molecular recognition of alkylammonium contact ion-pairs using a ditopic receptor. , 2003, The Journal of organic chemistry.

[63]  Feihe Huang,et al.  Ion pairing in fast-exchange host-guest systems: concentration dependence of apparent association constants for complexes of neutral hosts and divalent guest salts with monovalent counterions. , 2003, Journal of the American Chemical Society.

[64]  Z. Zhong,et al.  A self-assembled homooxacalix[3]arene-based dimeric capsule constructed by a Pd(II)-pyridine interaction which shows a novel chiral twisting motion in response to guest inclusion. , 2001, Journal of the American Chemical Society.

[65]  S. Kubik Large Increase in Cation Binding Affinity of Artificial Cyclopeptide Receptors by an Allosteric Effect , 1999 .

[66]  H. Gibson,et al.  Syntheses of Monofunctional Derivatives of m-Phenylene-16-crown-5, Bis(m-phenylene)-32-crown-10, and m-Phenylene-p-phenylene-33-crown-10 , 1997 .