Design, physico-chemical characterisation, toxicity and application of newly class of functionalized ionic liquids

Aleksandar Tot

Please use this identifier to cite or link to this item: https://open.uns.ac.rs/handle/123456789/19620

Title:	Design, physico-chemical characterisation, toxicity and application of newly class of functionalized ionic liquids Dizajniranje, fizičko-hemijska karakterizacija, toksičnost i primena nove klase funkcionalizovanih jonskih tečnosti
Authors:	Aleksandar Tot
Keywords:	Ionic liquids, synthesis, physico-chemical charaterisation, computational simulations, toxicity;Jonske tečnosti, sinteza, fizičko-hemijska svojstva, računarske simulacije, toksičnost
Issue Date:	3-Jul-2019
Publisher:	Univerzitet u Novom Sadu, Prirodno-matematički fakultet u Novom Sadu University of Novi Sad, Faculty of Sciences at Novi Sad
Abstract:	<p>U  ovoj  doktorskoj  disertaciji  sintetisane  su  dve  različite  klase jonskih  tečnosti,  na  bazi  imidazolijuma  i  holinijuma,  sa  ciljem snižavanja  toksičnosti.  Imidazolijumove  jonske  tečnosti  su funkcionalizovane  hidroksilnom  i  etarskom  grupom  u  bočnom lancu. Uspe&scaron;nost sinteza jonskih tečnosti potvrđena je  snimanjem IC  i  NMR  spektara.  Izmerene  su  gustine,  viskoznosti  i provodljivosti  čistih  imidazolijumovih  i  holinijumskih  jonskih tečnosti.  Na  osnovu  dobijenih  eksperimentalnih  rezultata,potpomognutim  računarskim  simulacijama  diskutovana  je strukturna organizacija između katjona i anjona. Utvrđeno je da prisustvo  hidroksilne  grupe  u  bočnom  lancu  imidazolovog katjona,  značajno  utiče  na  lokaciju  anjona  i  samim  tim  na makroskopska  svojstva.  U  nastavku  su  izmerene  gustine  i viskoznosti  vodenih  rastvora  sa  ciljem  dobijanja  informacija  o uticaju  dodatka  holinijumskih  i  imidazolijumovih  jonskih tečnosti  na  strukturu  vode.  Na  osnovu  B  koeficijenta  iz<br />viskoznosti,  ekspanzibilnosti  i  rezultata  simulacija  molekulske dinamike,  utvrđeno  je  da  sve  jonske  tečnosti  imaju  structure making  osobine.  Takođe,  na  osnovu  izračunatih  specifičnih molarnih zapremina i doking analize na receptoru za gorak ukus,<br />ustanovljeno je da vodeni rastvori holinijumskih jonskih tečnosti imaju gorak ukus.<br />Toksičnost funkcionalizovanih imidazolijumovih jonskih tečnosti ispitana je na  nekoliko biljnih vrsta  (p&scaron;enica, ječam i krastavac), kao i na larvama  <em>A.  salina</em>  i ćelijskoj liniji MRC-5. Potvrđeno jeda  uvođenje  hidroksilne  grupe  u  alkil  niz  najvi&scaron;e  se  redukuju<br />toksičnosti  imidazolijumovih  jonskih  tečnosti,  dok  je  uticaj etarske  grupe  na  smanjenje  toksičnosti  značajno  manji. Ispitivanje  citotoksičnosti  i  antibakterijske  aktivnosti  ukazalo  je da holinijumske jonske tečnosti se mogu smatrati netoksičnima, i<br />pokazuju  beningnije  dejstvo  u  poređenju  sa  njihovim  polaznim komponentama  (askorbinska  kiselina,  biotin  i  nikotinska kiselina).</p> <p><!--[if gte mso 9]><xml> <w:WordDocument> <w:View>Normal</w:View> <w:Zoom>0</w:Zoom> <w:TrackMoves/> <w:TrackFormatting/> <w:PunctuationKerning/> <w:ValidateAgainstSchemas/> <w:SaveIfXMLInvalid>false</w:SaveIfXMLInvalid> <w:IgnoreMixedContent>false</w:IgnoreMixedContent> <w:AlwaysShowPlaceholderText>false</w:AlwaysShowPlaceholderText> <w:DoNotPromoteQF/> <w:LidThemeOther>EN-US</w:LidThemeOther> <w:LidThemeAsian>X-NONE</w:LidThemeAsian> <w:LidThemeComplexScript>X-NONE</w:LidThemeComplexScript> <w:Compatibility> <w:BreakWrappedTables/> <w:SnapToGridInCell/> <w:WrapTextWithPunct/> <w:UseAsianBreakRules/> <w:DontGrowAutofit/> <w:SplitPgBreakAndParaMark/> <w:DontVertAlignCellWithSp/> 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table.MsoNormalTable{mso-style-name:"Table Normal";mso-tstyle-rowband-size:0;mso-tstyle-colband-size:0;mso-style-noshow:yes;mso-style-priority:99;mso-style-qformat:yes;mso-style-parent:"";mso-padding-alt:0in 5.4pt 0in 5.4pt;mso-para-margin-top:0in;mso-para-margin-right:0in;mso-para-margin-bottom:10.0pt;mso-para-margin-left:0in;line-height:115%;mso-pagination:widow-orphan;font-size:11.0pt;font-family:"Calibri","sans-serif";mso-ascii-font-family:Calibri;mso-ascii-theme-font:minor-latin;mso-fareast-font-family:"Times New Roman";mso-fareast-theme-font:minor-fareast;mso-hansi-font-family:Calibri;mso-hansi-theme-font:minor-latin;mso-bidi-font-family:"Times New Roman";mso-bidi-theme-font:minor-bidi;}</style><![endif]--></p><p class="MsoNormal">In  this  doctoral  thesis,  ionic  liquids  based  on  imidazolium  and cholinium cation were synthesized, in order to obtain new class of ILs with reduced toxicity. Imidazolium based ionic liquids were functionalized  with hydroxyl and ether  group in   order to reduce their  lipophilicity.  All  newly  synthesized  compounds  were  confirmed  by  measuring  IR  and  NMR  spectra.  For  pure  ionic  liquids, density, conductivity and viscosity were measured. Based on  the  obtained  experimental  results  supported  with  results  of  molecular simulations, it was concluded that presence of oxygen in  alkyl  side  chain  of  imidazolium  ionic  liquids  significantly contribute to position of anion. Further,  density  and  viscosity  of  diluted  aqueous  ILs  solutions were  measured  with  a  purpose  to  investigate  their  influence  on water  structure.  Based  on  obtained  values  for  viscosicty  B coefficient,  expansibility  and  from  MD  simulations,  all  ionic  liquids  express  structure  making  tendency.  From  calculated specific  apparent  molar  volumes  for  cholinium  ionic  liquids  it was noted bitter taste.  The  toxicity  of  functionalized  imidazolium  ionic  liquids  was investigated  on  different  plant  species  (wheat ,  barley  and cucumber),  on  larvae  of <em><span style="font-family:"Calibri","sans-serif";mso-ascii-theme-font:minor-latin;mso-hansi-theme-font:minor-latin;mso-bidi-font-family:"Times New Roman";mso-bidi-theme-font:minor-bidi"> A.  salina</span></em>  and  cell  line  MRC-5.  From<br />obtained  results  it  was  concluded  that  introduction  of  hydroxyl group in alkyl side chain reduce toxicity significantly more than  ether  group.  Experiments  on  cytotoxicicity  and  antibacterial effects  allowed  to  conclude  that  those  newly  synthesized cholinium ionic liquids can be considered as non-toxic.</p>
URI:	https://open.uns.ac.rs/handle/123456789/19620
Appears in Collections:	PMF Teze/Theses

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