Semi-Telechelic Polymers from Mechanochemical C─C Bond Activation

Rony Schwarz; Charles E. Diesendruck

doi:10.1002/advs.202304571

Semi-Telechelic Polymers from Mechanochemical C─C Bond Activation

Rony Schwarz, Charles E. Diesendruck

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

3 Scopus citations

Abstract

Unstrained C─C bond activation is attained in homopolymers through mechanochemical bond scission followed by functionalization to yield mostly semi-telechelic polymer chains. Ball milling poly(ethylene oxide) (PEO) in the presence of 1-(bromoacetyl)pyrene (BAPy) yields the pyrene terminated PEO. Similarly, milling with 2,4′-dibromoacetophenone followed by Suzuki coupling allows the introduction of various aryl end groups. PEOs with a molecular weight below 20 kDa show no functionalization, supporting a mechanochemical mechanism. The protocol is also tested with doxorubicin, yielding the drug-polymer conjugate. PEO halogenation is also demonstrated by milling PEO with iodine, N-bromosuccinimide, or N-iodosuccinimide, which can then be reacted with an amine substituted anthracene. Grinding additional carbon polymers with BAPy indicates that this functionalization method is general for different polymer chemistries.

Original language	English
Article number	2304571
Journal	Advanced Science
Volume	10
Issue number	34
DOIs	https://doi.org/10.1002/advs.202304571
State	Published - 6 Dec 2023
Externally published	Yes

Keywords

ball milling
c─c activation
doxorubicin
halogenation
mechanochemistry

ASJC Scopus subject areas

Medicine (miscellaneous)
General Chemical Engineering
General Materials Science
Biochemistry, Genetics and Molecular Biology (miscellaneous)
General Engineering
General Physics and Astronomy

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10.1002/advs.202304571

Cite this

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title = "Semi-Telechelic Polymers from Mechanochemical C─C Bond Activation",

abstract = "Unstrained C─C bond activation is attained in homopolymers through mechanochemical bond scission followed by functionalization to yield mostly semi-telechelic polymer chains. Ball milling poly(ethylene oxide) (PEO) in the presence of 1-(bromoacetyl)pyrene (BAPy) yields the pyrene terminated PEO. Similarly, milling with 2,4′-dibromoacetophenone followed by Suzuki coupling allows the introduction of various aryl end groups. PEOs with a molecular weight below 20 kDa show no functionalization, supporting a mechanochemical mechanism. The protocol is also tested with doxorubicin, yielding the drug-polymer conjugate. PEO halogenation is also demonstrated by milling PEO with iodine, N-bromosuccinimide, or N-iodosuccinimide, which can then be reacted with an amine substituted anthracene. Grinding additional carbon polymers with BAPy indicates that this functionalization method is general for different polymer chemistries.",

keywords = "ball milling, c─c activation, doxorubicin, halogenation, mechanochemistry",

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AU - Diesendruck, Charles E.

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N2 - Unstrained C─C bond activation is attained in homopolymers through mechanochemical bond scission followed by functionalization to yield mostly semi-telechelic polymer chains. Ball milling poly(ethylene oxide) (PEO) in the presence of 1-(bromoacetyl)pyrene (BAPy) yields the pyrene terminated PEO. Similarly, milling with 2,4′-dibromoacetophenone followed by Suzuki coupling allows the introduction of various aryl end groups. PEOs with a molecular weight below 20 kDa show no functionalization, supporting a mechanochemical mechanism. The protocol is also tested with doxorubicin, yielding the drug-polymer conjugate. PEO halogenation is also demonstrated by milling PEO with iodine, N-bromosuccinimide, or N-iodosuccinimide, which can then be reacted with an amine substituted anthracene. Grinding additional carbon polymers with BAPy indicates that this functionalization method is general for different polymer chemistries.

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KW - ball milling

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KW - halogenation

KW - mechanochemistry

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Semi-Telechelic Polymers from Mechanochemical C─C Bond Activation

Abstract

Keywords

ASJC Scopus subject areas

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