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Synthesis and characterization of polyrotaxane-based molecular nanotubes prepared from α-cyclodextrin/chlorinated polyethylene glycol complex end capped with 4-ethylaniline

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Abstract

An aqueous solution of chlorinated polyethylene glycol (Cl-PEG-Cl) and α-cyclodextrin (α-CD) was used to form inclusion complexes, which several α-CDs are threaded into the linear PEG chain and produced a so-called polypseudorotaxane (PPRx). By attaching 4-ethylaniline as the blocking agent to the chlorinated PEG chain ends, the complex will be stabilized, resulting in the formation of so-called polyrotaxane (PRx) (also known as molecular necklace). Finally, crosslinked αCD-based PRx with a tubular structure was formed via the condensation reactions between α-cyclodextrins and epichlorohydrin. Using concentrated NaOH solution, polymer chains were then removed from complexes, resulting in the so-called molecular tube (MT). This novel method led to the improvement in polyrotaxane conversion with less production steps and reduced materials overall costs. Resulting products in each section were characterized by 1H and 13C nuclear magnetic resonance spectroscopies (1H-NMR and 13C-NMR), from which complex inclusion ratio and length of the nanotubes were estimated. XRD was also used to confirm tubular structure of the inclusion complexes.

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Notes

  1. (Benzotriazol-1-yloxy)tris(dimethylamino)-phosphonium hexafluorophosphate.

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Acknowledgements

The authors would like to acknowledge the Tarbiat Modares University (Grant number # 81586) for the financial support.

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Authors and Affiliations

  1. Polymer Reactions Engineering Department, Faculty of Chemical Engineering, Tarbiat Modares University, P.O. Box: 14155/143, Tehran, Islamic Republic of Iran

    Nima Pakzad, Mahdi Abdollahi & Mohammad Ali Semsarzadeh

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  1. Nima Pakzad
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  2. Mahdi Abdollahi
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  3. Mohammad Ali Semsarzadeh
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Contributions

NP: Experimental design; Carrying out measurements; Formal analysis; Investigation; Methodology; Validation; Writing—original draft; MA: Conceptualization; Data curation; Funding acquisition; Investigation; Project administration; Supervision; Writing—review & editing. MAS: Conceptualization, Project administration; Supervision; Writing—review & editing.

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Correspondence to Mahdi Abdollahi or Mohammad Ali Semsarzadeh.

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Pakzad, N., Abdollahi, M. & Semsarzadeh, M.A. Synthesis and characterization of polyrotaxane-based molecular nanotubes prepared from α-cyclodextrin/chlorinated polyethylene glycol complex end capped with 4-ethylaniline. Polym. Bull. 81, 4661–4676 (2024). https://doi.org/10.1007/s00289-023-04936-w

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