Hexakis(m-phenylene ethynylene) Macrocycles with Multiple H-Bonding Side Chains and Modified Cavities: Altered Stacking Strength and Persistent Tubular Assembly.

Hexakis(m-phenylene ethynylene) macrocycles 1 bearing multiple hydrogen-bonding side chains and containing inner cavities modified with different functional groups are synthesized based on Pd-catalyzed (Sonogashira) coupling of monomeric building blocks to trimeric precursors that are recombined and coupled to give macrocycles with different substitution patterns of inward-pointing groups. Examining four representative macrocycles indicates that they all undergo the same helical tubular assembly previously observed for macrocycle 1a but with different stacking strengths.

[1]  Fayez Y. Al-mkhaizim,et al.  Persistent Organic Nanopores Amenable to Structural and Functional Tuning. , 2016, Journal of the American Chemical Society.

[2]  T. Szyperski,et al.  Discrete stacking of aromatic oligoamide macrocycles. , 2015, Journal of the American Chemical Society.

[3]  Ka Yi Yung,et al.  Extremely strong tubular stacking of aromatic oligoamide macrocycles† †Electronic supplementary information (ESI) available. See DOI: 10.1039/c4sc02380c Click here for additional data file. , 2014, Chemical science.

[4]  Huaqiang Zeng,et al.  Proton gradient-induced water transport mediated by water wires inside narrow aquapores of aquafoldamer molecules. , 2014, Journal of the American Chemical Society.

[5]  C. Didierjean,et al.  Macrocyclic arylopeptoids--a novel type of cyclic N-alkylated aromatic oligoamides forming nanotubular assemblies. , 2014, Chemical communications.

[6]  S. Höger,et al.  Fluctuating exciton localisation in giant pi-conjugated spoked-wheel macrocycles , 2015, 1507.06536.

[7]  Yo Shimizu,et al.  Syntheses and properties of graphyne fragments: trigonally expanded dehydrobenzo[12]annulenes. , 2013, Chemistry.

[8]  A. Flood,et al.  A pentagonal cyanostar macrocycle with cyanostilbene CH donors binds anions and forms dialkylphosphate [3]rotaxanes. , 2013, Nature chemistry.

[9]  B. Gong,et al.  Self-assembling organic nanotubes with precisely defined, sub-nanometer pores: formation and mass transport characteristics. , 2013, Accounts of chemical research.

[10]  B. Gong,et al.  Cavity-containing, backbone-rigidified foldamers and macrocycles. , 2012, Chemical communications.

[11]  Peter D. Frischmann,et al.  Sterically-limited self-assembly of Pt4 macrocycles into discrete non-covalent nanotubes: porous supramolecular tetramers and hexamers. , 2012, Chemistry.

[12]  Jeffrey S. Moore,et al.  Directional cyclooligomers via alkyne metathesis. , 2012, Journal of the American Chemical Society.

[13]  Hui Li,et al.  Self-assembling subnanometer pores with unusual mass-transport properties , 2012, Nature Communications.

[14]  M. Hansen,et al.  Empty helical nanochannels with adjustable order from low-symmetry macrocycles. , 2011, Angewandte Chemie.

[15]  H. Su,et al.  Persistently folded circular aromatic amide pentamers containing modularly tunable cation-binding cavities with high ion selectivity. , 2010, Journal of the American Chemical Society.

[16]  W Seth Childers,et al.  Peptide membranes in chemical evolution. , 2009, Current opinion in chemical biology.

[17]  J. Rebek.  Molecular behavior in small spaces. , 2009, Accounts of chemical research.

[18]  B. Gong,et al.  Aromatic oligoamide macrocycles from the bimolecular coupling of folded oligomeric precursors , 2009 .

[19]  B. Gong,et al.  Highly conducting transmembrane pores formed by aromatic oligoamide macrocycles. , 2008, Journal of the American Chemical Society.

[20]  S. Matile,et al.  Artificial beta-barrels. , 2008, Accounts of chemical research.

[21]  K. Kirshenbaum,et al.  Fit to be tied: conformation-directed macrocyclization of peptoid foldamers. , 2007, Organic letters.

[22]  Andrew J. Wilson,et al.  Macrocyclic scaffolds derived from p-aminobenzoic acid. , 2007, Chemical communications.

[23]  D. Pasini,et al.  Macrocycles as Precursors for Organic Nanotubes , 2007 .

[24]  Tohru Nishinaga,et al.  Giant macrocycles composed of thiophene, acetylene, and ethylene building blocks. , 2006, Journal of the American Chemical Society.

[25]  V. Lynch,et al.  Coordination of oxovanadium(V) in an expanded porphyrin macrocyclet. , 2006, Chemical communications.

[26]  G. Tew,et al.  Liquid crystalline order from ortho-phenylene ethynylene macrocycles. , 2006, Journal of the American Chemical Society.

[27]  Kyoung-Jin Chang,et al.  Oligoindole-based foldamers with a helical conformation induced by chloride. , 2005, Journal of the American Chemical Society.

[28]  R. Sijbesma,et al.  Hierarchical self-assembly of columnar aggregates. , 2005, Chemical Society reviews.

[29]  M. Sosnowski,et al.  Easy, inexpensive and effective oxidative iodination of deactivated arenes in sulfuric acid , 2004 .

[30]  Hua Guo,et al.  Highly efficient, one-step macrocyclizations assisted by the folding and preorganization of precursor oligomers. , 2004, Journal of the American Chemical Society.

[31]  J. Leger,et al.  Strained aromatic oligoamide macrocycles as new molecular clips. , 2004, Organic letters.

[32]  S. Höger,et al.  Shape-persistent macrocycles: from molecules to materials. , 2004, Chemistry.

[33]  Y. Yamaguchi,et al.  Shape-persistency and molecular function in heteromacrocycles: creation of heteroarenecyclynes and arene-azaarenecyclynes. , 2003, Chemistry.

[34]  Jeffrey S. Moore,et al.  Shape-persistent arylene ethynylene macrocycles: syntheses and supramolecular chemistry. , 2003, Chemical communications.

[35]  A. Schlüter,et al.  Shape‐Persistent, Nano‐Sized Macrocycles , 2002 .

[36]  G. Maas,et al.  Dirhodium(II) tetrakis(perfluoroalkylbenzoates) as partially recyclable catalysts for carbene transfer reactions with diazoacetates , 2002 .

[37]  D. Gin,et al.  Polymerized lyotropic liquid crystal assemblies for materials applications. , 2001, Accounts of chemical research.

[38]  H. Bayley,et al.  Stochastic sensors inspired by biology , 2001, Nature.

[39]  Yves Rubin,et al.  Polyethynylated cyclic π-systems: scaffoldings for novel two and three-dimensional carbon networks , 1999 .

[40]  Jeffrey S. Moore,et al.  High Resolution X‐ray Diffraction Study of a Tubular Liquid Crystal , 1998 .

[41]  D. Seebach,et al.  Cyclo‐β‐peptides: Structure and tubular stacking of cyclic tetramers of 3‐aminobutanoic acid as determined from powder diffraction data , 1997 .

[42]  S. Höger,et al.  Synthesis and X‐ray Structure of a Shape‐Persistent Macrocyclic Amphiphile , 1996 .

[43]  Juan R. Granja,et al.  Self-assembling organic nanotubes based on a cyclic peptide architecture , 1993, Nature.

[44]  Jeffrey S. Moore,et al.  Efficient synthesis of nanoscale macrocyclic hydrocarbons , 1992 .