A Pb²⁺-binding polychelatogen derived from thionated lactide

Abstract

The synthesis and characterization of a polychelatogen derived from thionated lactide is reported.

Thiocarbonyl chemistry in polymer science

“…Likewise, monomer 20 could be organocatalytically polymerized with retention of the thiocarbonyl function. 106 This use of a thiourea as a polymerization catalyst demonstrates another application of CvS functional molecules in polymer science. 101 Several similar catalysts (along with their oxo-urea analogues) have been investigated for the ringopening of δ-valerolactone, ε-caprolactone, and lactide.…”

“…Likewise, monomer 20 could be organocatalytically polymerized with retention of the thiocarbonyl function. 106…”

“…Similar polymerization of ethylene carbonate leads to ether linkages due to loss of carbon dioxide 103 Organocatalytic Retention of thiocarbonyl 1,5,7-Triazabicyclo[4.4.0]dec-5-ene (TBD, organocatalyst) and 4-methyl benzyl alcohol (initiator) 104 Proceeds via retention of the thiocarbonyl bond, without an S-O isomerism, different to 17, reportedly due to the use of an organocatalyst; 18a was shown to polymerize the fastest due the additional ring strain of the trans configuration of the xanthate ring; 18b was thought to be faster than 18c due to C-S bonds being weaker and easier to break than C-O bonds Organocatalytic S-O isomerism BEMP, r.t 105. Produces only the thioester polymer, through an irreversible mechanism; similar to the DBU ringopening of ε-thionocaprolactone 16, however no trace of the thionoester is found Organocatalytic Retention of thiocarbonyl DMAP, DBU, thiourea106 …”

Syntheses and chemical transformations of glycolide and lactide as monomers for biodegradable polymers

“…The resulting monomer was used to obtain functional polymers and copolymers that serve as the polymer base of porous scaffolds. Yet another widely known method implies obtaining a thionated lactide derivative by treating L-lactide with a mixture of phosphorous pentasulfide (P4S10) and hexamethyldisiloxane (HMDO) [311]. Along similar lines, thionated lactide can act as a dienophile when interacting with cyclopentadiene by the reaction of thio-Diels -Alder.…”

Polymer sequestrants for biological and environmental applications

“…For example, while cobalt is biologically important as a component of vitamin B 12 , elevated concentrations can lead to adverse effects on the heart, liver and kidneys . Recent advances in polymer chemistry have enabled the design of complex polymer architectures that have high affinity for heavy metal ions . Equally important, recovery of heavy metal ions from wastewater could be a sustainable process, as industrial manufacturing relies heavily on these elements …”