Synthesis and Crystal Structure of Tetraalkyl Resorcinarene Octa[N-(2-pyridylmethyl)acetamides]

doi:10.11944/j.issn.1000-0518.2015.12.150206

Chinese Journal of Applied Chemistry ›› 2015, Vol. 32 ›› Issue (12): 1416-1422.DOI: 10.11944/j.issn.1000-0518.2015.12.150206

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Synthesis and Crystal Structure of Tetraalkyl Resorcinarene Octa[N-(2-pyridylmethyl)acetamides]

MU Huarong^a,YAO Yong^b,YAN Chaoguo^b^*()

^aCollege of Chemical Engineering,Yangzhou Polytechnic Institute,Yangzhou,Jiangsu 225127,China
^bCollege of Chemistry & Chemical Engineering,Yangzhou University,Yangzhou,Jiangsu 225002,China

Received:2015-06-18 Accepted:2015-08-27 Published:2015-12-01 Online:2015-12-01
Contact: YAN Chaoguo
Supported by:
Supported by the National Natural Science Foundation of China(No.20972132, No.2130111)

Abstract

Abstract:

In order to deeply investigate the assembly and function of supramolecular topological structures based on the skeleton of carlixarenes, we launched the study on the synthesis and molecular structures of resorcinarene octasubstituted pyridymethylacetamides. A series of tetraalkyl resorcinarene octa[N-(2-pyridylmethyl)acetamides] was prepared by sequential alkylation of resorcinarene with methyl α-chloroacetate and ammonolysis of the corresponding resorcinarene octaacetates with 2-aminomethylpyridine. Single crystal structures of tetrapropyl resorcinarene acetate, tetrapropyl and tetrahexyl resorcinarene octa(N-2-pyridylmethylacetamides) obtained by X-ray diffraction method indicate that the resorcinarene core adopts rccc(all cis) conformation with two resorcinol rings almost perpendicular to the other two resorcinol rings, four alkyl groups stretching to the lower rim and octa[N-(2-pyridylmethyl)acetamides] groups stretching outside.

Key words: macrocyclic compound, resorcinarene, pyridine, crystal structure, molecular configuration

MU Huarong, YAO Yong, YAN Chaoguo. Synthesis and Crystal Structure of Tetraalkyl Resorcinarene Octa[N-(2-pyridylmethyl)acetamides][J]. Chinese Journal of Applied Chemistry, 2015, 32(12): 1416-1422.

References

[1]	Bohmer B. Calixarenes, Macrocycles with(almost) Unlimited Possibilities[J]. Angew Chem Int Ed Engl,1995,34(7):713-745.
[2]	Creaven B S,Donlon D F,McGinley J. Coordination Chemistry of Calix[4]arene Derivatives with Lower Rim Functionalisation and Their Applications[J]. Coord Chem Rev,2009,253(7/8):893-962.
[3]	Jasat A,Sherman J C. Carceplexes and Hemicarceplexes[J]. Chem Rev,1999,99(4):931-968.
[4]	Conn M M,Rebek J Jr. Self-assembling Capsules[J]. Chem Rev,1997,97(5):1647-1668.
[5]	Timmerman P,Verboom W,Reinhoudt D N. Resorcinarenes[J]. Tetrahedron,1996,52(8):2663-2704.
[6]	Biros S M,Rebek J Jr,Structure and Binding Properties of Water-soluble Cavitands and Capsules[J]. Chem Soc Rev,2007,36(1):93-104.
[7]	Kumari H,Deakyne C A,Atwood J L. Solution Structures of Nanoassemblies Based on Pyrogallol[4]arenes[J]. Acc Chem Res,2014,47(10):3080-3088.
[8]	Iwanek W,Fröhlich R,Urbaniak M,et al.The Complexes of Tetramethylresorc[4]arene with Amines, Amino Alcohols and Pyridine[J]. Tetrahedron,1998,54(46):14031-14040.
[9]	Alexander W. Calixarene-encapsulated Nanoparticles:Selfassembly into Functional Nanomaterials[J]. Chem Commun,2006,(15):1581-1591.
[10]	Dionisio M,Schnorr J M,Michaelis J K,et al.Cavitand-Functionalized SWCNTs for N-Methylammonium Detection[J]. J Am Chem Soc,2012,134(15):6540-6543.
[11]	Sander J,Bu?ar D K,Baltrusaitis J,MacGillivray L R. Organic Nanocrystals of the Resorcinarene Hexamer via Sonochemistry:Evidence of Reversed Crystal Growth Involving Hollow Morphologies[J]. J Am Chem Soc,2012,134(16):6900-6903.
[12]	Yamanaka M,Kawaharada M,Nito Y,et al.Structural Alteration of Hybrid Supramolecular Capsule Induced by Guest Encapsulation[J]. J Am Chem Soc,2011,133(41):16650-16656.
[13]	Zhang Q,Tiefenbacher K. Hexameric Resorcinarene Capsule is a Brønsted Acid:Investigation and Application to Synthesis and Catalysis[J]. J Am Chem Soc,2013,135(43):16213-16219.
[14]	Hong M L,Zhang Y M,Liu Y. Selective Binding Affinity Between Quaternary Ammonium Cations and Water-Soluble Calix[4]resorcinarene[J]. J Org Chem,2015,80(3):1849-1855
[15]	Han J,Yan C G. Synthesis, Crystal Structure and Configuration of Resorcinarene Amides[J]. J Incl Phenom Macrocycl Chem,2008,63(1/2):119-126.
[16]	Sun J,Liu D M,Wang J X,et al.Regioselective Synthesis of Calix[4]arene 1,3-Di and Monosubstituted Sulfur-containing Schiff Bases[J]. J Incl Phenom Macrocycl Chem,2009,64(3/4):317-324.
[17]	Han J,Cai Y H,Liu L,et al. Syntheses, Crystal Structures, and Electrochemical Properties of Multi-ferrocenyl Resorcinarenes[J]. Tetrahedron,2007,63(10):2275-2282.
[18]	Yan C G,Chen W F,Chen J,et al.Microwave Irradiation Assisted Synthesis, Alkylation Reaction, and Configuration Analysis of Aryl Pyrogallol[4]arenes[J]. Tetrahedron,2007,63(39):9614-9620.
[19]	McIldowie M J,Mocerino M,Skelton B W,et al. Facile Lewis Acid Catalyzed Synthesis of C4 Symmetric Resorcinarenes[J]. Org Lett,2000,2(30):3869-3871.
[20]	Yan C G,Li L,Liu W L. Metallic Macrocycle with a 1,3-Alternate Calix[4]arene Salicylideneamine Ligand[J]. J Coord Chem,2009,62(13):2118-2124.
[21]	Sun J,Liu D M,Yan C C, Transition Metal Complexes of Bidentate p-tert-Butylcalix[4]arene Salkyldithiocarbazate Schiff Bases[J]. J Coord Chem,2009,62(14):2337-2346.
[22]	Sun Y,Yan C G,Yao Y,et al.Self-Assembly and Metallization of Resorcinarene Microtubes in Water[J]. Adv Funct Mater,2008,18(23):3981-3990.
[23]	Shen M,Sun Y,Han Y,et al.Strong Deaggregating Effect of a Novel Polyamino Resorcinarene Surfactant on Gold Nanoaggregates under Microwave Irradiation[J]. Langmuir,2008,24(22):13161-13167.
[24]	Sun Y,Yao Y, Yan C G,et al. Selective Decoration of Metal Nanoparticles Inside or Outside of Organic Microstructures via Self-Assembly of Resorcinarene[J]. ACS Nano,2010,4(4):2129-2141.
[25]	Yao Y,Sun Y,Han Y,et al.Preparation of Resorcinarene-Functionalized Gold Nanoparticles and Their Catalytic Activities for Reduction of Aromatic Nitro Compounds[J]. Chinese J Chem,2010,28(5):705-712.
[26]	Li L,Sun J,Zhang L L,et al.Crystal Structure and Fluorescence Sensing Properties of Tetramethoxyresorcinarene Functionalized Schiff Bases[J]. J Mol Struct,2015,1081:355-361.
[27]	Joseph R,Ramanujam B,Acharya A,et al.Fluorescence Switch-on Sensor for Cu2+ by an Amide Linked Lower Rim 1,3-Bis(2-picolyl)amine Derivative of Calix[4]arene in Aqueous Methanol[J]. Tetrahedron Lett,2009,50(23):2735-2739.

Synthesis and Crystal Structure of Tetraalkyl Resorcinarene Octa[N-(2-pyridylmethyl)acetamides]

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