Evidence for a Bulky Unit of a Pillar[5]arene Flipping in the Solid State

It is well known that pillar[5]arenes have two most stable conformations (pS and pR) in their crystal structures. Because of the intramolecular H-bonding interactions, substituents, temperature, solvent and so on, the rotational behaviors of the phenolic units on pillararenes are also common. This paper showed some other kinds of conformations in the functionalized pillar[5]arenes and gave evidence for a bulky unit (1,4-methoxycarbonylmethoxybenzene unit) flipping in the solid state. The presence of hydrogen bonding facilitated the intermolecular self-assembly in terms of energy-minimized packing in the crystals. Thus, the main driving force for the flipping of this bulky unit might be both the intramolecular hydrogen bonding between the phenolic units on pillararenes and quadrupolar hydrogen bonding between the host and water. This paper helps us to have a better understanding on the conformations of pillar[5]arenes.

[1]  Xi-long Qiu,et al.  Acetylcholine-triggered cargo release from supramolecular nanovalves based on different macrocyclic receptors. , 2014, Chemistry.

[2]  M. Pan,et al.  Synthesis of a Pillar[5]arene with Both Hydroxyl and Methoxycarbonyl‐Methoxy Groups and Its Host‐Guest Complexation with a Bis(imidazolium) Salt , 2014 .

[3]  Feihe Huang,et al.  A pillar[5]arene/imidazolium [2]rotaxane: solvent- and thermo-driven molecular motions and supramolecular gel formation , 2014 .

[4]  M. Pan,et al.  Pillar[5]arene derivatives with three different kinds of repeating units: first examples, crystal structures and selective preparation , 2014 .

[5]  Feihe Huang,et al.  LCST‐Type Phase Behavior Induced by Pillar[5]arene/Ionic Liquid Host–Guest Complexation , 2013, Advanced materials.

[6]  M. Pan,et al.  A pillar[2]arene[3]hydroquinone which can self-assemble to form a molecular zipper in the solid state , 2013 .

[7]  J. F. Stoddart,et al.  Mechanized silica nanoparticles based on pillar[5]arenes for on-command cargo release. , 2013, Small.

[8]  J. F. Stoddart,et al.  Stereochemical inversion in difunctionalised pillar[5]arenes , 2013 .

[9]  Yanyan Zhang,et al.  Supramolecular polymers with tunable topologies via hierarchical coordination-driven self-assembly and hydrogen bonding interfaces , 2013, Proceedings of the National Academy of Sciences.

[10]  Feihe Huang,et al.  A pillar[6]arene with mono(ethylene oxide) substituents: synthesis and complexation with diquat. , 2013, Chemical communications.

[11]  Yanhui Shi,et al.  Hierarchical self-assembly: well-defined supramolecular nanostructures and metallohydrogels via amphiphilic discrete organoplatinum(II) metallacycles. , 2013, Journal of the American Chemical Society.

[12]  M. Pan,et al.  Selective Preparation of Isomeric Tetrahydroxypillar[5]arenes and Pillar[3]arene[2]quinones , 2013 .

[13]  Yong Wang,et al.  Gold nanoparticles stabilized by an amphiphilic pillar[5]arene: preparation, self-assembly into composite microtubes in water and application in green catalysis , 2013 .

[14]  Yi Pan,et al.  pH-responsive supramolecular vesicles based on water-soluble pillar[6]arene and ferrocene derivative for drug delivery. , 2013, Journal of the American Chemical Society.

[15]  T. Ogoshi,et al.  An amphiphilic pillar[5]arene as efficient and substrate-selective phase-transfer catalyst. , 2013, Organic letters.

[16]  Feihe Huang,et al.  A sugar-functionalized amphiphilic pillar[5]arene: synthesis, self-assembly in water, and application in bacterial cell agglutination. , 2013, Journal of the American Chemical Society.

[17]  Xiao‐Yu Hu,et al.  A novel redox-responsive pillar[6]arene-based inclusion complex with a ferrocenium guest. , 2013, Chemical communications.

[18]  Zhan-Ting Li,et al.  Chiral selective transmembrane transport of amino acids through artificial channels. , 2013, Journal of the American Chemical Society.

[19]  Ying-Wei Yang,et al.  Viologen-mediated assembly of and sensing with carboxylatopillar[5]arene-modified gold nanoparticles. , 2013, Journal of the American Chemical Society.

[20]  Feihe Huang,et al.  A supramolecular cross-linked conjugated polymer network for multiple fluorescent sensing. , 2013, Journal of the American Chemical Society.

[21]  Ying-Wei Yang,et al.  One-pot synthesis of pillar[n]arenes catalyzed by a minimum amount of TfOH and a solution-phase mechanistic study. , 2012, Organic & biomolecular chemistry.

[22]  J. F. Stoddart,et al.  Incorporation of an A1/A2-difunctionalized pillar[5]arene into a metal-organic framework. , 2012, Journal of the American Chemical Society.

[23]  Yue Ding,et al.  Multistimuli Responsive Supramolecular Cross-Linked Networks On the Basis of the Benzo-21-Crown-7/Secondary Ammonium Salt Recognition Motif , 2012 .

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

[25]  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.

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

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

[28]  Bo Zheng,et al.  Stimuli-responsive supramolecular polymeric materials. , 2012, Chemical Society reviews.

[29]  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.

[30]  Yi Pan,et al.  Novel [2]pseudorotaxanes constructed by self-assembly of bis-urea-functionalized pillar[5]arene and linear alkyl dicarboxylates. , 2012, Chemical communications.

[31]  Jing Sun,et al.  Efficient Construction and Structure Determination of Novel Macrocycles with Calixarene Bishydrazones , 2012 .

[32]  Mingming Zhang,et al.  A Crown Ether Appended Super Gelator with Multiple Stimulus Responsiveness , 2012, Advanced materials.

[33]  A. Kaifer,et al.  Pronounced pH effects on the kinetics of cucurbit[7]uril-based pseudorotaxane formation and dissociation. , 2012, Chemical communications.

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

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

[36]  D. Leigh,et al.  A three-compartment chemically-driven molecular information ratchet. , 2012, Journal of the American Chemical Society.

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

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

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

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

[41]  Ying Han,et al.  Synthesis of triptycene-derived macrotricyclic host containing two dibenzo-[18]-crown-6 moieties and its complexation with paraquat derivatives: Li(+)-ion-controlled binding and release of the guests in the complexes. , 2012, The Journal of organic chemistry.

[42]  Xia Ding,et al.  A Multiresponsive, Shape‐Persistent, and Elastic Supramolecular Polymer Network Gel Constructed by Orthogonal Self‐Assembly , 2012, Advanced materials.

[43]  K. Rissanen,et al.  Chelate cooperativity and spacer length effects on the assembly thermodynamics and kinetics of divalent pseudorotaxanes. , 2012, Journal of the American Chemical Society.

[44]  Zhenxia Chen,et al.  Synthesis of pillar[5]arene dimers and their cooperative binding toward some neutral guests. , 2012, Organic letters.

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

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

[47]  Yajie Zhang,et al.  Formation of polypseudorotaxane networks by cross-linking the quadruple hydrogen bonded linear supramolecular polymers via bisparaquat molecules. , 2011, Chemical communications.

[48]  T. Ogoshi,et al.  "Clickable" pillar[5]arenes. , 2011, Chemical communications.

[49]  D. Qu,et al.  Construction of Polypseudorotaxane from Low-Molecular Weight Monomers via Dual Noncovalent Interactions , 2011 .

[50]  Sarah J. Vella,et al.  Rotaxanes Based on the 1,2‐Bis(pyridinio)ethane–24‐Crown‐8 Templating Motif , 2011 .

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

[52]  J. Steed,et al.  Anion tuning and polymer templating in a simple low molecular weight organogelator. , 2011, Chemical communications.

[53]  Chuan-feng Chen.  Novel triptycene-derived hosts: synthesis and their applications in supramolecular chemistry. , 2011, Chemical communications.

[54]  S. Fujinami,et al.  Facile, rapid, and high-yield synthesis of pillar[5]arene from commercially available reagents and its X-ray crystal structure. , 2011, The Journal of organic chemistry.

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

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

[57]  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.

[58]  Chuan-feng Chen,et al.  Isomeric squaraine-based [2]pseudorotaxanes and [2]rotaxanes: synthesis, optical properties, and their tubular structures in the solid state. , 2010, Chemistry.

[59]  Feihe Huang,et al.  Syntheses of copillar[5]arenes by co-oligomerization of different monomers. , 2010, Organic letters.

[60]  C. Schalley,et al.  Integrative self-sorting: construction of a cascade-stoppered hetero[3]rotaxane. , 2008, Journal of the American Chemical Society.

[61]  Chuan-Feng Chen,et al.  Efficient potassium-ion-templated synthesis and controlled destruction of [2]rotaxanes based on cascade complexes. , 2008, The Journal of organic chemistry.

[62]  Ning Li,et al.  Self-sorting organization of two heteroditopic monomers to supramolecular alternating copolymers. , 2008, Journal of the American Chemical Society.

[63]  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.

[64]  Jiuming He,et al.  Palladium(II)-directed self-assembly of dynamic donor-acceptor [2]catenanes. , 2008, Organic letters.

[65]  Chuan-feng Chen,et al.  A highly efficient approach to [4]pseudocatenanes by threefold metathesis reactions of a triptycene-based tris[2]pseudorotaxane. , 2005, Journal of the American Chemical Society.

[66]  Feihe Huang,et al.  A supramolecular triarm star polymer from a homotritopic tris(crown ether) host and a complementary monotopic paraquat-terminated polystyrene guest by a supramolecular coupling method. , 2005, Journal of the American Chemical Society.

[67]  Hao Wang,et al.  Supramolecular aggregates constructed from gold nanoparticles and l-try-CD polypseudorotaxanes as captors for fullerenes. , 2005, Journal of the American Chemical Society.

[68]  Leyong Wang,et al.  Multiple Catenanes Derived from Calix[4]arenes , 2004, Science.

[69]  Feihe Huang,et al.  A cryptand/bisparaquat [3]pseudorotaxane by cooperative complexation. , 2003, Journal of the American Chemical Society.

[70]  Feihe Huang,et al.  First pseudorotaxane-like [3]complexes based on cryptands and paraquat: self-assembly and crystal structures. , 2003, Journal of the American Chemical Society.

[71]  Kimoon Kim,et al.  Self-assembly of a polyrotaxane containing a cyclic ''bead'' in every structural unit in the solid state: Cucurbituril molecules threaded on a one-dimensional coordination polymer , 1996 .