Preparation of poly(oxanorbornene) based single and double-folding polymers via nucleophilic aromatic substitution reaction

Burcu Alkan; Binnur Aydogan Temel; Hakan Durmaz; Gokhan Temel

doi:10.1016/j.eurpolymj.2023.112694

Preparation of poly(oxanorbornene) based single and double-folding polymers via nucleophilic aromatic substitution reaction

Burcu Alkan, Binnur Aydogan Temel, Hakan Durmaz^*, Gokhan Temel

^*Corresponding author for this work

Department of Chemistry

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

5 Citations (Scopus)

Abstract

A facile approach is introduced to prepare single-chain nanoparticles (SCNPs) utilizing intramolecular crosslinking based on nucleophilic aromatic substitution reaction. The linear polymeric precursor comprising dichlorotriazine (DCT) moiety as a reactive pendant group is synthesized via ring-opening metathesis polymerization (ROMP). The reactive chlorine atoms on DCT motifs are substituted with a dithiol nucleophile in varying degrees to yield individually intramolecularly crosslinked polymer nanoparticles. In addition, double-collapse and modification reactions are exploited through the substitution reaction from the remaining unreacted chlorine atoms. A significant reduction in hydrodynamic volumes of the corresponding SCNPs is observed compared to their linear analogues. The obtained nanoparticles are characterized by size exclusion chromatography (SEC), proton nuclear magnetic resonance spectroscopy (¹H NMR), diffusion-ordered spectroscopy (DOSY), dynamic light scattering (DLS), and transmission electron microscopy (TEM) techniques.

Original language	English
Article number	112694
Journal	European Polymer Journal
Volume	203
DOIs	https://doi.org/10.1016/j.eurpolymj.2023.112694
Publication status	Published - 19 Jan 2024

Bibliographical note

Publisher Copyright:
© 2023 Elsevier Ltd

Funding

This work was supported by the Scientific Research Projects Departments of Istanbul Technical University (ITU BAP Project Number: TDK-2023-44655 ). B. A. T. acknowledges the resources and support from the Drug Application and Research Center (ILMER) at Bezmialem Vakif University.

Funders	Funder number
Drug Application and Research Center
ILMER
Istanbul Teknik Üniversitesi
Bezmialem Vakıf Üniversitesi
Bilimsel Araştırma Projeleri Birimi, İstanbul Teknik Üniversitesi	TDK-2023-44655

Keywords

Chain folding
Cyanuric chloride
Ring-opening metathesis polymerization
Single–chain nanoparticles
Soft nanoparticles

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10.1016/j.eurpolymj.2023.112694

Cite this

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title = "Preparation of poly(oxanorbornene) based single and double-folding polymers via nucleophilic aromatic substitution reaction",

abstract = "A facile approach is introduced to prepare single-chain nanoparticles (SCNPs) utilizing intramolecular crosslinking based on nucleophilic aromatic substitution reaction. The linear polymeric precursor comprising dichlorotriazine (DCT) moiety as a reactive pendant group is synthesized via ring-opening metathesis polymerization (ROMP). The reactive chlorine atoms on DCT motifs are substituted with a dithiol nucleophile in varying degrees to yield individually intramolecularly crosslinked polymer nanoparticles. In addition, double-collapse and modification reactions are exploited through the substitution reaction from the remaining unreacted chlorine atoms. A significant reduction in hydrodynamic volumes of the corresponding SCNPs is observed compared to their linear analogues. The obtained nanoparticles are characterized by size exclusion chromatography (SEC), proton nuclear magnetic resonance spectroscopy (1H NMR), diffusion-ordered spectroscopy (DOSY), dynamic light scattering (DLS), and transmission electron microscopy (TEM) techniques.",

keywords = "Chain folding, Cyanuric chloride, Ring-opening metathesis polymerization, Single–chain nanoparticles, Soft nanoparticles",

author = "Burcu Alkan and Temel, {Binnur Aydogan} and Hakan Durmaz and Gokhan Temel",

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doi = "10.1016/j.eurpolymj.2023.112694",

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T1 - Preparation of poly(oxanorbornene) based single and double-folding polymers via nucleophilic aromatic substitution reaction

AU - Alkan, Burcu

AU - Temel, Binnur Aydogan

AU - Durmaz, Hakan

AU - Temel, Gokhan

PY - 2024/1/19

Y1 - 2024/1/19

N2 - A facile approach is introduced to prepare single-chain nanoparticles (SCNPs) utilizing intramolecular crosslinking based on nucleophilic aromatic substitution reaction. The linear polymeric precursor comprising dichlorotriazine (DCT) moiety as a reactive pendant group is synthesized via ring-opening metathesis polymerization (ROMP). The reactive chlorine atoms on DCT motifs are substituted with a dithiol nucleophile in varying degrees to yield individually intramolecularly crosslinked polymer nanoparticles. In addition, double-collapse and modification reactions are exploited through the substitution reaction from the remaining unreacted chlorine atoms. A significant reduction in hydrodynamic volumes of the corresponding SCNPs is observed compared to their linear analogues. The obtained nanoparticles are characterized by size exclusion chromatography (SEC), proton nuclear magnetic resonance spectroscopy (1H NMR), diffusion-ordered spectroscopy (DOSY), dynamic light scattering (DLS), and transmission electron microscopy (TEM) techniques.

AB - A facile approach is introduced to prepare single-chain nanoparticles (SCNPs) utilizing intramolecular crosslinking based on nucleophilic aromatic substitution reaction. The linear polymeric precursor comprising dichlorotriazine (DCT) moiety as a reactive pendant group is synthesized via ring-opening metathesis polymerization (ROMP). The reactive chlorine atoms on DCT motifs are substituted with a dithiol nucleophile in varying degrees to yield individually intramolecularly crosslinked polymer nanoparticles. In addition, double-collapse and modification reactions are exploited through the substitution reaction from the remaining unreacted chlorine atoms. A significant reduction in hydrodynamic volumes of the corresponding SCNPs is observed compared to their linear analogues. The obtained nanoparticles are characterized by size exclusion chromatography (SEC), proton nuclear magnetic resonance spectroscopy (1H NMR), diffusion-ordered spectroscopy (DOSY), dynamic light scattering (DLS), and transmission electron microscopy (TEM) techniques.

KW - Chain folding

KW - Cyanuric chloride

KW - Ring-opening metathesis polymerization

KW - Single–chain nanoparticles

KW - Soft nanoparticles

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DO - 10.1016/j.eurpolymj.2023.112694

M3 - Article

AN - SCOPUS:85185846807

SN - 0014-3057

VL - 203

JO - European Polymer Journal

JF - European Polymer Journal

M1 - 112694

ER -

Preparation of poly(oxanorbornene) based single and double-folding polymers via nucleophilic aromatic substitution reaction

Abstract

Bibliographical note

Funding

Keywords

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