Jozef Hodyl PhD Thesis - Theses - Flinders University

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236. C. Lopez, R. M. Claramount and J. Elguero, Arkivoc, 2008, iv, 33-46.237. J. L. Atwood, J. E. D. Davies, D.D.MacNicol and F. Vogtle, eds.,Comprehensive Supramolecular Chemistry, Elsevier Science Ltd,Oxford, 1996.238. D. D. Laws, H. M. L. Bitter and A. Jerschow, Angew. Chem. Int. Ed.Engl., 2002, 41, 3096-3129.239. K. Masuda, S.Tabata, H. Kono, Y. Sakata, T. Hayase, E. Yonemochi andK. Terada, Int. J. Pharm., 2006, 318, 146-153.240. J. H. Yang, Y. Ho and D. L. M. Tzou, Magn. Reson. Chem., 2007, 46,718-725.241. D. D. Perrin and W. L. F. Armarego, Purification of LaboratoryChemicals, 3rd edn., Pergamon Press, Oxford, 1982.242. J. Zubrick, Organic Chem Lab Survival manual: a student's guide totechniques, J. Wiley and Sons, New York, 1997.243. Wavemetrics, Manual Revision 4/2005 5.04B ed., Wavemetrics Inc.,Lake Oswego, OR, 2005.244. D. B. Amabilino, P. L. Anelli, P. R. Ashton, G. R. Brown, E. Cordova,L. A. Godinez, W. Hayes, A. E. Kaifer, D. Philip, A. M. Z. Slavin, N.Spencer, J. F. Stoddart, M. S. Tolley and D. J. Williams, J. Am. Chem.Soc., 1995, 117, 11142-11170.245. J. S. Beck, J. C. VartUli, W. J. Roth, M. E. Leonowicz, C. T. Kresge, K.D. Schmitt, C. T-W. Chu, D. H. Olson, E. W. Sheppard, S. B. McCullen,J. B. Higgins and J. L. Schlenker, J. Am. Chem. Soc., 1992, 114, 10834-10843.246. V. M. S. Gil and N. C. Oliveira, J. Chem. Educ., 1990, 67, 473-478.182
247. W. Likussar and D. F. Botz, Anal. Chem., 1971, 43, 1265-1272.183
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Silica Immobilised MetalIon Activat
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ABSTRACTImmobilisation of functiona
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DECLARATIONI certify that this thes
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EtOHGPDMSGPDMESGPSGPTSethanolglycid
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CHAPTER ONEINTRODUCTION
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The focus of this work was to prepa
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sequestering anions has proved to b
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ange of pH due to its high basicity
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nitrophenol or p-nitrophenolate wit
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It has been shown by NMR and crysta
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within the cavity of a p-tert-butyl
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60 in 0.5% DMSO-MeCN (v/v). 82 The
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synthesised bi- tri- and tetra - π
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adopt a trans-III conformation, whe
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amide oxygen atoms on the pendant a
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apparent there is, nonetheless, evi
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However, hetero-N-substitution on t
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Si-OH +- OH SiO - + H 2 OFor surfac
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35This material was obtained with a
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OOSiOHOROR OSiOHOOOSiOSiOSiOSiOSiOS
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Tetraaza metal complexes immobilise
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CHAPTER TWOSYNTHESIS OF MACROCYCLIC
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In addition, successful immobilisat
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3233Figure 2.3Reaction of 3-(glycid
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The methodology chosen was adapted
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agreed with literature values. 109R
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XS HO O H61, n = 262, n = 3n+ClOSO6
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anhydrous ethanol, Scheme 2.7. The
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75Figure 2.5 Structure of (S)-(-)-p
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metal ion coordination the pendant
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CHAPTER THREEGUEST MOLECULE INCLUSI
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3.1 where K A is the association, o
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0.5cχG∆δ∆δGbaχ GFigure 3.1S
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χG∆δ∆δGFigure 3.4 Job's Plot
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The downfield movement of the guest
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arm framework. The relative magnitu
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This phenomenon correlates well wit
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non-classical hydrogen bonding is g
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The full set of logK values obtaine
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such that they would indicate precl
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CHAPTER 4MODIFICATION OF THE SILICA
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Chemical modification of the silica
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GPTSGPDMESFigure 4.4Schematic depic
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GPS, 33, linker material with an ex
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free νOHτSiOHνSi-O-SiδH 2 Oasym
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224, 225the surface silanol groups.
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esonances, the spectrum for Si-GPS-
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increase in surface coverage from t
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and, more so due to the larger size
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CHAPTER 5METAL ION UPTAKE STUDIES W
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Scheme 5.1 Metal(II) ion coordinati
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linker material, Si-GPS, 33; endcap
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[Cd(Trac)](ClO 4 ) 2 , 94, or Si-GP
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CHAPTER 6GUEST MOLECULE INCLUSION S
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and D-histidinate. Guest inclusion
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Table 6.2Percent inclusion data for
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contains two hydroxy groups in the
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methoxy group, as portrayed by the
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these guest molecules with receptor
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only about half of that taken up by
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Percent inclusion values for these
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Table 6.7Percent guest inclusion of
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6.1.7 Guest inclusion studies with
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A1 3542Neutral GuestBAnionic GuestH
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A1 46 7532 Anionic Guest8BCHostHost
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extent, meta-positioned hydroxy gro
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δ obs (ppm)6.2146.2136.2126.2116.2
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CHAPTER 7EXPERIMENTAL7.1 General Ex
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inding constants (logK values) and
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delay time of 4 s. 13 C CPMAS NMR s
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C, -CH 2 - CH 2 OSO 2 ); 68.11 (1 C
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A solution of 69 (2.00 g, 10.1 mmol
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Bn, meta); 127.79 (1 C, Bn, para);
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added in a single portion. The mixt
Page 151 and 152: dioxane): δ 158.67 (1 C, C=O); 135
Page 153 and 154: 1-(benzyloxycarbonyl)-4,7,10-tris-(
Page 155 and 156: 1,4,7-tris-((S)-2-hydroxy-3-phenoxy
Page 157 and 158: 1,4,7-tris(S)-2-hydroxy-3-[4-((2-(2
Page 159 and 160: 1,4,7-tris(S)-2-hydroxy-3-[4-(2-(2-
Page 161 and 162: 1-(2-hydroxypropyl)-4,7,10-tris-((S
Page 163 and 164: 7.11 Preparation of the silica mate
Page 165 and 166: To a suspension of 33 (1.48 g, 1.1
Page 167 and 168: gel-like suspension that was cooled
Page 169 and 170: Si-GPS-Tri-Trac, 4545The title comp
Page 171 and 172: APPENDIX ABINDING CONSTANT DETERMIN
Page 173 and 174: 1.01000.880δ obs (ppm)0.60.4logK =
Page 175 and 176: APPENDIX BDETERMINATION OF STOICHIO
Page 177 and 178: 0.5χG∆δGFigure B.2χ GSimulated
Page 179 and 180: 13 C CPMAS NMR SPECTRA OF SOME HIGH
Page 181 and 182: Si-GPS-[Cd(Trac)(2,5-diydroxybenzoa
Page 183 and 184: REFERENCES
Page 185 and 186: 15. D. Tzalis and Y. Tor, Tetrahedr
Page 187 and 188: 42. A. P. Davis and R. S.Wareham, A
Page 189 and 190: 69. R. J. Bergeron, M. A. Channing
Page 191 and 192: 93. C. B. Smith, A. K. W. Stephens,
Page 193 and 194: 118. D. D. Dischino, E. J. Delaney,
Page 195 and 196: 144. X. Huang, X. Chang, Q. He, Y.
Page 197 and 198: 169. J. M. Klunder, T. Onami and K.
Page 199 and 200: 197. K. A. Connors, Binding Constan
Page 201: 221. J. Blumel, J. Am. Chem. Soc.,
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Jozef Hodyl PhD Thesis - Theses - Flinders University

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