Research article

Synthesis of inositol-based star polymers through low ppm ATRP methods

Corresponding Author

Paweł Chmielarz

[email protected]

orcid.org/0000-0002-9101-6264

Department of Physical Chemistry, Faculty of Chemistry, Rzeszow University of Technology, Al. Powstańców Warszawy 6, 35-959 Rzeszow, Poland

Correspondence to: Paweł Chmielarz, Department of Physical Chemistry, Faculty of Chemistry, Rzeszow University of Technology, Al. Powstańców Warszawy 6, 35-959 Rzeszow, Poland

E-mail: [email protected]

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Paweł Chmielarz,

Corresponding Author

Paweł Chmielarz

[email protected]

orcid.org/0000-0002-9101-6264

Department of Physical Chemistry, Faculty of Chemistry, Rzeszow University of Technology, Al. Powstańców Warszawy 6, 35-959 Rzeszow, Poland

Correspondence to: Paweł Chmielarz, Department of Physical Chemistry, Faculty of Chemistry, Rzeszow University of Technology, Al. Powstańców Warszawy 6, 35-959 Rzeszow, Poland

E-mail: [email protected]

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First published: 15 May 2017

https://doi.org/10.1002/pat.4065

Citations: 32

Notes: The author declares no competing financial interest.

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Abstract

The vitamin B₈-based macroinitiator with six 2-bromoisobutyric initiating sites was prepared for the first time by the transesterification reaction of meso-inositol with 2-bromoisobutyryl bromide. A series of six-armed (co)polymers, containing hydrophilic poly(di(ethylene glycol) methyl ether methacrylate) and amphiphilic poly(di(ethylene glycol) methyl ether methacrylate)-block-poly(methyl methacrylate) as the arms and meso-inositol as the core, were obtained by low ppm atom transfer radical polymerization (ATRP) methods, utilizing 30 ppm of catalyst complex. Under Fe⁰-mediated supplemental activators and reducing agents ATRP, Cu⁰-mediated supplemental activators and reducing agents ATRP, Ag⁰-mediated activators regenerated by electron transfer ATRP, and simplified electrochemically mediated ATRP conditions, polymerization proceeded on to high conversion while maintaining low dispersity (Đ = 1.05–1.16) giving well-defined six-armed star (co)polymers. ¹H NMR spectral results confirm the formation of new star-shaped block (co)polymers. The absence of intermolecular coupling reactions during synthesis was confirmed by gel permeation chromatography analyses of the side chains of received star (co)polymers. These vitamin B₈-based star (co)polymers may find biomedical applications as thermo-sensitive drug delivery systems, biosensors, and tissue engineering solutions. Copyright © 2017 John Wiley & Sons, Ltd.

Supporting Information

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Data S1. Supporting info item

Fig. S1. Synthesis of meso-inositol-Br₆ multifuntional ATRP initiator.

Fig. S2. ¹H–NMR analysis of meso-inositol-Br₆ (M_n = 1,070, Ð = 1.03) after purification (in CDCl₃).

Fig. S3. Cyclic voltammetry results of Cu^IIBr₂/TPMA (black) and in the presence of vitamin-based Ino-Br₆ macroinitiator (gray). The arrow (green) indicates the applied potential during electrolysis. Measurement conditions: [DEGMA]/[Ino-Br₆ (per –Br)]/[Cu^IIBr₂/TPMA] = 60/1/0.0018, [DEGMA] = 2.7 M, [Cu^IIBr₂/TPMA] = 0.08 mM, [TBAP] = 0.2 mM, T = 55 °C. Table 1, entries 4−5.

Fig. S4. GPC traces of DEGMA polymerization in the presence of Ino-Br₆ via (a) Fe⁰-mediated SARA ATRP, (b) Cu⁰-mediated SARA ATRP, (c) Ag⁰-mediated ARGET ATRP, (d) seATRP under constant potential conditions and (e) seATRP under multistep constant current conditions. GPC traces of MMA simplified eATRP in the presence of Ino-(PDEGMA-Br)₆ under (f) constant potential electrolysis and (g) constant current electrolysis.

Fig. S5. Multi-step electrolysis for seATRP; (a) results from applied potential (black line) and applied current (gray line) conditions, (b) first-order kinetic plots of ln([M]₀/[M]) vs time, and (c) M_n and M_w/M_n values vs monomer conversion for electrolysis under constant potential/current approach. Reaction conditions: [DEGMA]/[Ino-Br₆ (per –Br)]/[Cu^IIBr₂/TPMA] = 60/1/0.0018, [DEGMA] = 2.7 M, [Cu^IIBr₂/TPMA] = 0.08 mM, [TBAP] = 0.2 mM, T = 55 °C. Table 1, entries 4−5.

Fig. S6. Cyclic voltammetry results of Cu^IIBr₂/TPMA (black) and in the presence of Ino-(PDEGMA-Br)₆ (gray). The arrow (green) indicates the applied potential during electrolysis. Measurement conditions: [MMA]/[Ino-(PDEGMA-Br)₆ (per –Br)]/[Cu^IIBr₂/TPMA] = 40/1/0.0012, [MMA] = 1.0 M, [Cu^IIBr₂/TPMA] = 0.03 mM, [TBAP] = 0.2 M, T = 55 °C. Table 1, entries 6−7.

Fig. S7. First-order kinetic plots for electrolysis under constant potential/current conditions. Reaction conditions: [MMA]/[Ino-(PDEGMA-Br)₆ (per –Br)]/[Cu^IIBr₂/TPMA] = 40/1/0.0012, [MMA] = 1.0 M, [Cu^IIBr₂/TPMA] = 0.03 mM, [TBAP] = 0.2 M, T = 55 °C. Table 1, entries 6−7.

Fig. S8. GPC traces of (a−e) PDEGMA arms cleaved from the inositol-based star polymers (Table 1 and 2, entries 1−5); GPC traces of (f−g) PDEGMA-b-PMMA arms cleaved from the inositol-based star copolymers (Table 1 and 2, entries 6−7).

Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.

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Volume28, Issue12

December 2017

Pages 1804-1812

Synthesis of inositol-based star polymers through low ppm ATRP methods

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Synthesis of inositol-based star polymers through low ppm ATRP methods

Abstract

Supporting Information

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Citing Literature

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