Degradable Polyphosphoramidate via Ring-Opening Metathesis Polymerization

Yifei Liang; Hao Sun; Wei Cao; Matthew P. Thompson; Nathan C. Gianneschi

doi:10.1021/acsmacrolett.0c00401

Degradable Polyphosphoramidate via Ring-Opening Metathesis Polymerization

Yifei Liang, Hao Sun^*, Wei Cao, Matthew P. Thompson, Nathan C. Gianneschi

^*Corresponding author for this work

Chemistry

Research output: Contribution to journal › Article › peer-review

Abstract

We report the synthesis of a degradable polyphosphoramidate via ring-opening metathesis polymerization (ROMP) with the Grubbs initiator (IMesH2)(C5H5N)2(Cl)2Ru═CHPh. Controlled ROMP of a low ring strain diazaphosphepine-based cyclic olefin was achieved at low temperatures to afford well-defined polymers that readily undergo degradation in acidic conditions via the cleavage of the acid-labile phosphoramidate linkages. The diazaphosphepine monomer was compatible in random and block copolymerizations with phenyl and oligo(ethylene glycol) bearing norbornenes. This approach introduced partial or complete degradability into the polymer backbones. With this chemistry, we accessed amphiphilic poly(diazaphosphepine-norbornene) copolymers that could be used to prepare micellar nanoparticles.

Original language	English (US)
Pages (from-to)	1417-1422
Number of pages	6
Journal	ACS Macro Letters
Volume	9
Issue number	10
DOIs	https://doi.org/10.1021/acsmacrolett.0c00401
State	Published - Oct 20 2020

ASJC Scopus subject areas

Organic Chemistry
Polymers and Plastics
Inorganic Chemistry
Materials Chemistry

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title = "Degradable Polyphosphoramidate via Ring-Opening Metathesis Polymerization",

abstract = "We report the synthesis of a degradable polyphosphoramidate via ring-opening metathesis polymerization (ROMP) with the Grubbs initiator (IMesH2)(C5H5N)2(Cl)2Ru═CHPh. Controlled ROMP of a low ring strain diazaphosphepine-based cyclic olefin was achieved at low temperatures to afford well-defined polymers that readily undergo degradation in acidic conditions via the cleavage of the acid-labile phosphoramidate linkages. The diazaphosphepine monomer was compatible in random and block copolymerizations with phenyl and oligo(ethylene glycol) bearing norbornenes. This approach introduced partial or complete degradability into the polymer backbones. With this chemistry, we accessed amphiphilic poly(diazaphosphepine-norbornene) copolymers that could be used to prepare micellar nanoparticles. ",

author = "Yifei Liang and Hao Sun and Wei Cao and Thompson, {Matthew P.} and Gianneschi, {Nathan C.}",

note = "Funding Information: N.C.G. acknowledges support of this research from the NIH through the NHLBI (R01HL139001). Additional support was provided by the IMSERC at Northwestern University, which has received support from the Soft and Hybrid Nanotechnology Experimental (SHyNE) Resource (NSF ECCS-1542205), the State of Illinois, and the International Institute for Nanotechnology (IIN).",

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AU - Liang, Yifei

AU - Sun, Hao

AU - Cao, Wei

AU - Thompson, Matthew P.

AU - Gianneschi, Nathan C.

N1 - Funding Information: N.C.G. acknowledges support of this research from the NIH through the NHLBI (R01HL139001). Additional support was provided by the IMSERC at Northwestern University, which has received support from the Soft and Hybrid Nanotechnology Experimental (SHyNE) Resource (NSF ECCS-1542205), the State of Illinois, and the International Institute for Nanotechnology (IIN).

PY - 2020/10/20

Y1 - 2020/10/20

N2 - We report the synthesis of a degradable polyphosphoramidate via ring-opening metathesis polymerization (ROMP) with the Grubbs initiator (IMesH2)(C5H5N)2(Cl)2Ru═CHPh. Controlled ROMP of a low ring strain diazaphosphepine-based cyclic olefin was achieved at low temperatures to afford well-defined polymers that readily undergo degradation in acidic conditions via the cleavage of the acid-labile phosphoramidate linkages. The diazaphosphepine monomer was compatible in random and block copolymerizations with phenyl and oligo(ethylene glycol) bearing norbornenes. This approach introduced partial or complete degradability into the polymer backbones. With this chemistry, we accessed amphiphilic poly(diazaphosphepine-norbornene) copolymers that could be used to prepare micellar nanoparticles.

AB - We report the synthesis of a degradable polyphosphoramidate via ring-opening metathesis polymerization (ROMP) with the Grubbs initiator (IMesH2)(C5H5N)2(Cl)2Ru═CHPh. Controlled ROMP of a low ring strain diazaphosphepine-based cyclic olefin was achieved at low temperatures to afford well-defined polymers that readily undergo degradation in acidic conditions via the cleavage of the acid-labile phosphoramidate linkages. The diazaphosphepine monomer was compatible in random and block copolymerizations with phenyl and oligo(ethylene glycol) bearing norbornenes. This approach introduced partial or complete degradability into the polymer backbones. With this chemistry, we accessed amphiphilic poly(diazaphosphepine-norbornene) copolymers that could be used to prepare micellar nanoparticles.

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