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Chemical Structure| 160661-60-9 Chemical Structure| 160661-60-9

Structure of 6-Deoxy-6-thio-b-cyclodextrin
CAS No.: 160661-60-9

Chemical Structure| 160661-60-9

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O' ; Shea, KE ; Restrepo-Osorio, Rodrigo ;

Abstract: Poly- and perfluoroalkyl substances (PFAS) are pollutants of serious concern due to their adverse health effects, widespread use, and resistance to degradation. β-cyclodextrins (β-CDs) form strong β-CD:PFAS complexes with a wide variety of PFAS. We report herein the incorporation of ionizable functional groups on the primary rim of β-CD, to control the complexation of PFAS as a function of solution pH. The binding constants (KCD:PFAS) of short-chain and long-chain PFAS by amino-β-CDs and thiol-β-CDs decrease by 56 to 98 % with a change in solution pH from neutral to alkaline conditions. The observed reduction in binding constants (KCD:PFAS) with increased pH is assigned to the increased electrostatic repulsion between negatively charged functional group amended to the β-CD (host) and negatively charged PFAS polar head group (guest) under alkaline conditions. The inclusion of two pH-dependent ionizable functional groups to the host was achieved by employing 6-(3-hydroxybenzylamino)-6-deoxy-β- cyclodextrin [(3-OH)BnNHβ-CD]. The phenol functionality is converted from a neutral to an anionic species while the benzyl-amino group is cationic under neutral pH and converted to neutral charge under alkaline conditions, thus the β-CD host can be converted from a positive charge to a negative charge by varying solution pH. The (3-OH)BnNHβ-CD exhibits strong pH-modulated binding with long-chain perfluorocarboxylic acids (PFCAs), evidenced in an 88 % decrease in the association constant with PFOA under alkaline conditions. The association constant for (3-OH)BnNHβ-CD with hexafluoropropylene oxide dimer acid (HFPO-DA), a branched perfluoroether carboxylic acid (PFECA), however, decreases by nearly 50 % under alkaline conditions compared to an 81 % and 98 % decrease observed for mono-thiol and mono-amino β-CDs, respectively. A 95 % decrease in binding in PFOA is observed for mono-thiol-β-CD, while heptakis-(6-mercapto-6-deoxy)-β-cyclodextrin, with seven ionizable thiol groups leads to a modest 23 % decrease for complexation of PFOA with change from neutral to alkaline pH. Steric effects due to chain branching within PFAS in combination with size and number of substituents on the β-CD reduce the impact of pH effects on binding. This study demonstrates derivatization of β-CD with pH ionizable functional groups can be used to control the β-CD binding of PFAS as a possible strategy for the removal and recovery of PFAS from contaminated water streams.

Keywords: Host-guest complexation ; PFAS ; cyclodextrin ; remediation: pH

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Product Details of [ 160661-60-9 ]

CAS No. :160661-60-9
Formula : C42H70O28S7
M.W : 1247.44
SMILES Code : SC[C@@H]1[C@]2([H])[C@@H]([C@@H](O)[C@](O[C@]3([H])[C@H](O[C@@](O[C@]4([H])[C@H](O[C@@](O[C@]5([H])[C@H](O[C@@](O[C@@]6([H])[C@H](O)[C@@H](O)[C@@](O[C@@H]6CS)([H])O[C@@]7([H])[C@H](O)[C@@H](O)[C@@](O[C@@H]7CS)([H])O[C@@]8([H])[C@H](O)[C@@H](O)[C@@](O[C@@H]8CS)([H])O2)([H])[C@H](O)[C@H]5O)CS)([H])[C@H](O)[C@H]4O)CS)([H])[C@H](O)[C@H]3O)CS)([H])O1)O
MDL No. :MFCD30179373
InChI Key :MAQZFSOYQPJIOQ-UHFFFAOYSA-N
Pubchem ID :72995956

Safety of [ 160661-60-9 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302
Precautionary Statements:P280-P305+P351+P338

Application In Synthesis of [ 160661-60-9 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Upstream synthesis route of [ 160661-60-9 ]

[ 160661-60-9 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 30754-23-5 ]
  • [ 160661-60-9 ]
References: [1] Chemical Communications, 2012, vol. 48, # 65, p. 8063 - 8065.
[2] Chemical Communications, 2014, vol. 50, # 79, p. 11757 - 11759.
  • 2
  • [ 123155-24-8 ]
  • [ 160661-60-9 ]
References: [1] Chemical Communications, 2017, vol. 53, # 13, p. 2126 - 2129.
 

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