Intramolecular cyclization for stimuli-controlled depolymerization of polycaprolactone particles leading to disassembly and payload release

Caroline De Gracia Lux, Adah Almutairi

Research output: Contribution to journalArticle

31 Citations (Scopus)

Abstract

Polymers capable of on-demand, controlled depolymerization are an important tool in a broad variety of applications in science, technology, and industry. We report functionalized poly(caprolactone)s (PCL)s designed to allow on-demand and complete depolymerization through incorporation of pendant protected amino groups that, on deprotection, trigger nucleophilic attack and yield a single cyclic product. Two cleavable protecting groups were used to cap PCL: light sensititve o-nitrobenzyl alcohol (ONB) and tert-butyl carbamate (Boc; for proof of concept). NMR confirmed that PCL-Boc degrades completely into the designed intramolecular cyclization products within a day upon deprotection. TEM visualization of irradiated particles made from PCL-ONB encapsulating iron oxide nanoparticles reveals complete disruption of nanoparticles and release of payload. This work demonstrates that intramolecular cyclization within the polymer backbone is an excellent route to accelerate polymer degradation by backbiting reactions into small fragments that should be easily cleared from the circulation.

Original languageEnglish (US)
Pages (from-to)432-435
Number of pages4
JournalACS Macro Letters
Volume2
Issue number5
DOIs
StatePublished - May 27 2013

Fingerprint

Polycaprolactone
Depolymerization
Cyclization
Polymers
Alcohols
Nanoparticles
Carbamates
Iron oxides
Visualization
Nuclear magnetic resonance
Transmission electron microscopy
Degradation
polycaprolactone
Industry
2-nitrobenzyl alcohol

ASJC Scopus subject areas

  • Polymers and Plastics
  • Organic Chemistry
  • Inorganic Chemistry
  • Materials Chemistry

Cite this

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abstract = "Polymers capable of on-demand, controlled depolymerization are an important tool in a broad variety of applications in science, technology, and industry. We report functionalized poly(caprolactone)s (PCL)s designed to allow on-demand and complete depolymerization through incorporation of pendant protected amino groups that, on deprotection, trigger nucleophilic attack and yield a single cyclic product. Two cleavable protecting groups were used to cap PCL: light sensititve o-nitrobenzyl alcohol (ONB) and tert-butyl carbamate (Boc; for proof of concept). NMR confirmed that PCL-Boc degrades completely into the designed intramolecular cyclization products within a day upon deprotection. TEM visualization of irradiated particles made from PCL-ONB encapsulating iron oxide nanoparticles reveals complete disruption of nanoparticles and release of payload. This work demonstrates that intramolecular cyclization within the polymer backbone is an excellent route to accelerate polymer degradation by backbiting reactions into small fragments that should be easily cleared from the circulation.",
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