The supramolecular approach to the phase transfer of carboxylic calixresorcinarene-capped silver nanoparticles

Alina M. Ermakova1,2, Julia E. Morozova1,2, Yana V. Shalaeva1,2, Victor V. Syakaev1, Irek R. Nizameev1,3, Marsil K. Kadirov1, Igor S. Antipin1,2, Alexander I. Konovalov1
1A. E. Arbuzov Institute of Organic and Physical Chemistry, Kazan Scientific Center, Russian Academy of Science, Arbuzov str. 8, 420088 Kazan, Russian Federation
2Kazan Federal University, Kremlevskaya st. 18, 420008 Kazan, Russian Federation
3Kazan National Research Technical University, K. Marx str. 10, 420111 Kazan, Russian Federation

Tài liệu tham khảo

Ravindran, 2013, Biofunctionalized silver nanoparticles: advances and prospects, Colloids Surf. B, 105, 342, 10.1016/j.colsurfb.2012.07.036 Sperling, 2010, Surface modification, functionalization and bioconjugation of colloidal inorganic nanoparticles, Philos. Trans. R. Soc. A, 368, 1333, 10.1098/rsta.2009.0273 Yang, 2011, Phase transfer and its applications in nanotechnology, Chem. Soc. Rev., 40, 1672, 10.1039/B916790K Mayya, 2003, Phase transfer of surface-modified gold nanoparticles by hydrophobization with alkylamines, Langmuir, 19, 6987, 10.1021/la034018+ Cheng, 2004, Size-dependent phase transfer of gold nanoparticles from water into toluene by tetraoctylammonium cations: a wholly electrostatic interaction, J. Phys. Chem. B, 108, 24, 10.1021/jp036522t Wei, 2010, Reversible phase transfer of quantum dots and metal nanoparticles, Chem. Commun., 46, 3179, 10.1039/b926194j Yuan, 2011, Synthesis of highly fluorescent metal (Ag, Au, Pt, and Cu) nanoclusters by electrostatically induced reversible phase transfer, ACS Nano, 5, 8800, 10.1021/nn202860s Kwak, 2012, Electrochemical characterization of water-soluble Au25 nanoclusters enabled by phase-transfer reaction, J. Phys. Chem. Lett., 3, 2476, 10.1021/jz301059w Yang, 2006, Cyclodextrin as a capturing agent for redundant surfactants on Ag nanoparticle surface in phase transfer process, Colloids Surf. A, 290, 143, 10.1016/j.colsurfa.2006.05.016 Lala, 2001, Phase transfer of aqueous gold colloidal particles capped with inclusion complexes of cyclodextrin and alkanethiol molecules into chloroform, Langmuir, 17, 3766, 10.1021/la0015765 Chen, 2007, Phase transition of silver nanoparticles from aqueous solution to chloroform with the help of inclusion complexes of p-sulfonated calix[4]arene and alkanethiol molecules and its application in the size sorting of nanoparticles, Nanotechnology, 18, 175706, 10.1088/0957-4484/18/17/175706 Chen, 2008, Conversion of the surface property of oleic acid stabilized silver nanoparticles from hydrophobic to hydrophilic based on host-guest binding interaction, Langmuir, 24, 3471, 10.1021/la704020j Wang, 2003, Pulling nanoparticles into water: phase transfer of oleic acid stabilized monodisperse nanoparticles into aqueous solutions of γ-cyclodextrin, Nano Lett., 3, 1555, 10.1021/nl034731j Liu, 2001, Phase transfer of hydrophilic, cyclodextrin-modified gold nanoparticles to chloroform solutions, J. Am. Chem. Soc., 123, 11148, 10.1021/ja003957a Edwards, 2016, Manipulating the monolayer: responsive and reversible control of colloidal inorganic nanoparticle properties, ChemNanoMat, 2, 87, 10.1002/cnma.201500146 Nair, 2007, Silver nanoparticles: synthesis and therapeutic applications, J. Biomed. Nanotechnol., 3, 301, 10.1166/jbn.2007.041 Wei, 2015, Silver nanoparticles: synthesis, properties, and therapeutic applications, Drug. Discov. Today, 20, 595, 10.1016/j.drudis.2014.11.014 Montes-García, 2014, Metal nanoparticles and supramolecular macrocycles:a tale of synergy, Chem. Eur. J., 20, 10874, 10.1002/chem.201403107 Kongor, 2016, Calix-based nanoparticles: a review, Top. Curr. Chem., 374, 28, 10.1007/s41061-016-0029-z Chen, 2010, Cyclodextrin-functionalized silver nanoparticles for the naked eye detection of aromatic isomers, ACS Nano, 4, 6387, 10.1021/nn1016605 Tao, 2011, Cucurbit[n]urils as a SERS hot-spot nanocontainer through bridging gold nanoparticles, Chem. Commun., 47, 9867, 10.1039/c1cc12474a Tauran, 2011, Colourimetric and spectroscopic discrimination between nucleotides and nucleosides using para-sulfonato-calix[4]arene capped silver nanoparticles, Chem. Commun., 47, 10013, 10.1039/c1cc13175c Tauran, 2013, Anionic calixarene-capped silver nanoparticles show species-dependent binding to serum albumins, Molecules, 18, 5993, 10.3390/molecules18055993 Bian, 2010, para-Sulfonatocalix[6]arene-modified silver nanoparticles electrodeposited on glassy carbon electrode: preparation and electrochemical sensing of methyl parathion, Talanta, 81, 1028, 10.1016/j.talanta.2010.01.054 Sun, 2015, Highly sensitive chiral sensing by calix[4]arene-modified silver nanoparticles via dynamic light scattering, Sens. Actuator B, 216, 235, 10.1016/j.snb.2015.04.047 Hu, 2015, Highly sensitive colorimetric sensor for the detection of H2PO4− based on self-assembly of p-sulfonatocalix[6]arene modified silver nanoparticles, Sens. Actuator B, 218, 191, 10.1016/j.snb.2015.04.064 Xiong, 2008, Synthesis of para-sulfonatocalix [4]arene-modified silver nanoparticles as colorimetric histidine probes, Chem. Commun., 880, 10.1039/B716270G Guerrini, 2006, Functionalization of Ag nanoparticles with dithiocarbamate calix[4]arene as an effective supramolecular host for the surface-enhanced Raman scattering detection of polycyclic aromatic hydrocarbons, Langmuir, 22, 10924, 10.1021/la062266a Tauran, 2012, Calixarene silver nanoparticles interactions with surfactants are charge, size and critical micellar concentration dependent, Chem. Commun., 48, 9483, 10.1039/c2cc34670b Gannimani, 2016, γ-Cyclodextrin capped silver nanoparticles for molecular recognition and enhancement of antibacterial activity of chloramphenicol, J. Inorg. Biochem., 157, 15, 10.1016/j.jinorgbio.2016.01.008 Premkumar, 2010, Macrocycles as a tool: a facile and one-pot synthesis of silver nanoparticles using cucurbituril designed for cancer therapeutics, Chem. Eur. J., 16, 11563, 10.1002/chem.201001325 Tauran, 2015, Bio-applications of calix[n]arene capped silver nanoparticles, J. Nanosci. Nanotechnol., 15, 6308, 10.1166/jnn.2015.10850 Jain, 2011, Chemistry of calix[4]resorcinarenes, Russ. Chem. Rev., 80, 75, 10.1070/RC2011v080n01ABEH004127 Syakaev, 2008, Head-to-tail aggregates of sulfonatomethylated calix[4]resorcinarene in aqueous solutions, Supramol. Chem., 20, 453, 10.1080/10610270701310930 Syakaev, 2012, Guest controlled aggregation of amphiphilic sulfonatomethylated calix[4]resorcinarenes in aqueous solutions, J. Colloid Interface Sci., 370, 19, 10.1016/j.jcis.2011.12.069 Mironova, 2013, Crystal violet dye in complexes with amphiphilic anionic calix[4]resorcinarenes: binding by aggregates and individual molecules, J. Colloid Interface Sci., 407, 148, 10.1016/j.jcis.2013.06.048 Kazakova, 2013, Influence of amidoammonium calix[4]resorcinarenes on methyl orange protolytic equilibrium: supramolecular indicator systems, Supramol. Chem., 25, 831, 10.1080/10610278.2013.809085 Wei, 2006, Calixarene-encapsulated nanoparticles: self-assembly into functional nanomaterials, Chem. Commun., 158, 1581, 10.1039/b515806k Menon, 2013, Ultrasensitive and specific detection of dimethoate using a p-sulphonato-calix[4]resorcinarene functionalized silver nanoprobe in aqueous solution, RSC Adv., 3, 10623, 10.1039/c3ra40762d Nasretdinova, 2015, Electrochemical synthesis of silver nanoparticles in solution, Electrochem. Commun., 50, 69, 10.1016/j.elecom.2014.11.016 Sergeeva, 2016, Application of ferrocene-resorcinarene in silver nanoparticle synthesis, RSC Adv., 6, 87128, 10.1039/C6RA19961E Shen, 2007, Synthesis and characterization of water-soluble gold colloids stabilized with aminoresorcinarene, J. Phys. Chem. Solids, 68, 2252, 10.1016/j.jpcs.2007.06.007 Sun, 2008, Self-assembly and metallization of resorcinarene microtubes in water, Adv. Funct. Mater., 18, 3981, 10.1002/adfm.200800843 Sun, 2010, Selective decoration of metal nanoparticles inside or outside of organic microstructures via self-assembly of resorcinarene, ACS Nano, 4, 2129, 10.1021/nn901412n Makwana, 2015, Highly stable antibacterial silver nanoparticles as selective fluorescent sensor for Fe3+ ions, Spectrochim. Acta Part A, 134, 73, 10.1016/j.saa.2014.05.044 Ghoufi, 2004, Structures and energetics of complexes of the p-sulfonatocalix[4]arene with ammonium, alkylammonium, and tetraalkylammonium cations in water using molecular dynamics simulations, J. Phys. Chem. B, 108, 5095, 10.1021/jp037411x Hong, 2015, Selective binding affinity between quaternary ammonium cations and water-soluble calix[4]resorcinarene, J. Org. Chem., 80, 1849, 10.1021/jo502825z Kazakova, 2007, Stable complexes of tertiary ammonia derivative of phenothiazine with tertramethylsulfonated resorcin[4]arenes obtained under substoichiometric conditions, J. Incl. Phenom. Macrocycl. Chem., 59, 143, 10.1007/s10847-007-9307-2