Synthesis of para- and meta-imino- or -amino-methyl pyridyl-appended p-tert-butyl-calix[4]arene or p-tert-butyl-thiacalix[4]arene in 1,3-alternate conformation

Herein, the multistep synthesis of eight new ligands based on either calix[4]arene or thiacalix[4]arene backbone blocked in a 1,3-alternate conformation was achieved. Both types of backbones were functionalized with pyridyl coordinating units using either imino or amino junctions. The introduction of the pyridyl units was achieved using either the position 3 (meta) or 4 (para) of the aromatic moiety. Moreover, four out of the eight ligands were structurally investigated in the solid state via X-ray diffraction methods on single crystals.

[1]  S. Solovieva,et al.  Molecular tectonics: dimensionality and geometry control of silver coordination networks based on pyrazolyl appended thiacalixarenes , 2016 .

[2]  S. Solovieva,et al.  Molecular tectonics: silver coordination networks based on tetramercaptothiacalix[4]arene in 1,3-alternate conformation bearing four nitrile groups , 2015, Russian Chemical Bulletin.

[3]  S. Solovieva,et al.  Molecular tectonics: generation of grid and porous diamondoid coordination networks by calixarene based tectons , 2014 .

[4]  S. Solovieva,et al.  Molecular tectonics: anion control of dimensionality and connectivity in meta-pyridyl appended tetramercaptotetrathiacalix[4]arene based silver coordination networks. , 2014, Dalton transactions.

[5]  L. Wojtas,et al.  A calixarene based metal organic material, calixMOM, that binds potassium cations. , 2013, Chemical communications.

[6]  S. Solovieva,et al.  Molecular tectonics: p-H-thiacalix[4]arene pyridyl appended positional isomers as tectons for the formation of 1D and 2D mercury coordination networks. , 2013, Dalton transactions.

[7]  S. Solovieva,et al.  Molecular tectonics: control of the dimensionality in tetramercaptothiacalixarenes based coordination networks. , 2013, Inorganic chemistry.

[8]  W. Verboom,et al.  Pyrazine-functionalized calix[4]arenes: synthesis by palladium-catalyzed cross-coupling with phosphorus pronucleophiles and metal ion extraction properties , 2013 .

[9]  S. Solovieva,et al.  Molecular tectonics: pyridyl containing thiacalix[4]arene based tectons for the generation of 2- and 3-D silver coordination networks. , 2013, Dalton transactions.

[10]  K. V. Shabalin,et al.  Phenylurea-Equipped p-tert-Butylthiacalix[4]Arenes as the Synthetic Receptors for Monocharged Anions , 2013 .

[11]  Peyman Z. Moghadam,et al.  Calix[4]arene-based metal-organic frameworks: towards hierarchically porous materials. , 2012, Chemical communications.

[12]  Serkan Erdemir,et al.  Synthesis and electrochemical properties of calix[4]arene derivatives containing ferrocene units in the cone and 1,3-alternate conformation , 2012 .

[13]  Pratibha Sharma,et al.  Synthesis and metal extraction behavior of pyridine and 1,2,4-triazole substituted calix[4]arenes , 2010 .

[14]  T. Yamato,et al.  Synthesis and heteronuclear inclusion properties of a novel thiacalix[4]arene-based hard-soft receptor with 1,3-alternate conformation , 2010 .

[15]  I. Stoikov,et al.  p-tert-Butyl thiacalix[4]arenes functionalized at the lower rim by o-, m-, p-amido and o-, m-, p-(amidomethyl)pyridine fragments as receptors for α-hydroxy- and dicarboxylic acids , 2010 .

[16]  I. Stoikov,et al.  Synthesis and complexation properties of 1,3-alternate stereoisomers of p-tert-butylthiacalix[4]arenes tetrasubstituted at the lower rim by the phthalimide group , 2009 .

[17]  S. Solovieva,et al.  Molecular tectonics: 3-D organisation of decanuclear silver nanoclusters. , 2009, Chemical communications.

[18]  B. Creaven,et al.  Coordination chemistry of calix[4]arene derivatives with lower rim functionalisation and their applications , 2009 .

[19]  C. Chaix,et al.  Conformational analysis and anion-binding properties of ferrocenyl-calixarene receptors , 2009 .

[20]  S. Rahman,et al.  Allosteric bindings of thiacalix[4]arene-based receptors with 1,3-alternate conformation having two different side arms , 2008 .

[21]  S. Solovieva,et al.  Molecular tectonics: on the formation of 1-D silver coordination networks by thiacalixarenes bearing nitrile groups. , 2007, Dalton transactions.

[22]  M. Yamashita,et al.  Transition metal and lanthanide cluster complexes constructed with thiacalix[n]arene and its derivatives☆ , 2007 .

[23]  V. Böhmer,et al.  1,3-Alternate calix[4]arenes, selectively functionalized by amino groups. , 2005, Organic & biomolecular chemistry.

[24]  Y. Kondo,et al.  Potassium-thiacalix[8]arene assembly: structure and guest sorption profiles. , 2005, Chemical communications.

[25]  I. Goldberg,et al.  Supramolecular Design of Coordination Complexes of Silver(I) with Polyimine Ligands: Synthesis, Materials Characterization, and Structure of New Polymeric and Oligomeric Materials , 2003 .

[26]  Anthony L. Spek,et al.  Journal of , 1993 .

[27]  Thawatchai Tuntulani Zouhair Asfari, Volker Böhmer, Jack Harrowfield and Jacques Vicens (eds.), Calixarenes 2001. , 2002 .

[28]  I. Goldberg,et al.  Coordination polymers of transition metal ions with polydentate imine ligands. Syntheses, materials characterization, and crystal structures of polymeric complexes of copper(I), silver(I) and zinc(II) , 2002 .

[29]  J. Fischer,et al.  Tetrasulfinylcalix[4]arenes: Synthesis and solid state structural analysis , 1999 .

[30]  S. E. Matthews,et al.  Calix[4]arenes with CMPO functions at the narrow rim. Synthesis and extraction properties , 1999 .

[31]  J. Pansanel,et al.  Thiacalixarenes: Synthesis and structural analysis of thiacalix[4]arene and of p-tert-butylthiacalix[4]arene , 1998 .

[32]  J. Fischer,et al.  Sulfone-calixarenes: a new class of molecular building block , 1998 .

[33]  J. Fischer,et al.  Synthesis and structural analysis of an infinite linear coordination network formed by the self-assembly of tetracyanocalix[4]arene ligands and silver cations , 1998 .

[34]  Yoko Sato,et al.  Facile synthesis of p-tert-butylthiacalix[4]arene by the reaction of p-tert-butylphenol with elemental sulfur in the presence of a base , 1997 .