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Synthesis, characterization and end-functionalization of a novel telechelic star: styrene hexamer core carrying polyisobutylene arms fitted with allyl termini

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Abstract

The synthesis and characterization of a new star consisting of a hard styrene hexamer (St6) core of which emanate long soft polyisobutylene (PIB) arms and fitted with allyl (A) termini is documented. The synthesis was accomplished by a core-first strategy in two steps: (a) creating the core by living anionic hexamerization of 3-(2-methoxyisopropyl)styrene in essentially quantitative conversion with nearly targeted molar mass (Mn = 1450 g/mol) of very low dispersity (1.06), and (b) using this hexamer to produce in one pot PIB-A arms by living cationic polymerization of isobutylene (> 99% conversion), and terminating with allyltrimethylsilane. This is the first example of a star synthesis by anionic-to-cationic site transformation. Intermediates and final products were characterized by 1H NMR spectroscopy and GPC according to which the star had ~ 4.61 arms. The star was end-functionalized by thiol-ene clicking with furfuryl mercaptan (~ 85% yield) for the preparation of a furan-telechelic star.

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Acknowledgements

The authors thank the University of Akron and Bogazici University (Project No. 7089) for financial support.

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Authors and Affiliations

  1. Department of Chemistry, Polymer Research Center, Bogazici University, 34342, Istanbul, Turkey

    Turgut Nugay & Nihan Nugay

  2. Department of Polymer Science, The University of Akron, Akron, OH, 44325-3909, USA

    Turgut Nugay, Nihan Nugay & Joseph P. Kennedy

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  1. Turgut Nugay
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  2. Nihan Nugay
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Correspondence to Turgut Nugay.

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Nugay, T., Nugay, N. & Kennedy, J.P. Synthesis, characterization and end-functionalization of a novel telechelic star: styrene hexamer core carrying polyisobutylene arms fitted with allyl termini. Polym. Bull. 77, 5697–5710 (2020). https://doi.org/10.1007/s00289-019-03037-x

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  • DOI: https://doi.org/10.1007/s00289-019-03037-x

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