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Preparation of a star-type telechelic macrophotoinitiator of poly(ε-caprolactone) and its use in photoinduced free radical promoted cationic polymerization

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Abstract

A novel and well-defined four-arm star-type telechelic macrophotoinitiator of poly(ε-caprolactone) carrying benzoin photofunctional end-groups (PCL-BPI)4 was successfully synthesized by the combination of ring opening polymerization (ROP) and click chemistry techniques. First, hydroxyl end-functionalized four-arm (PCL-OH)4 was synthesized by ROP of ε-caprolactone (ε-CL) with pentaerythritol initiator. Then, the hydroxyl groups at the chain ends were converted to terminal alkyne groups by the condensation reaction between (PCL-OH)4 and 4-pentynoic acid to give an alkyne end-functionalized four-arm poly(ε-caprolactone), (PCL-alkyne)4, as the first click couple compound. Separately, an azido end-functionalized benzoin photoinitiator (BPI-N3) was prepared in two steps to be used as the other click couple compound. (PCL-alkyne)4 and BPI-N3 were coupled via “click chemistry” to prepare a well-defined four-arm star-type telechelic macrophotoinitiator, (PCL-BPI)4. In addition, the obtained (PCL-BPI)4 macrophotoinitiator was used in the photoinitiated free radical promoted cationic polymerization of cyclohexene oxide (CHO) to produce an (AB)4-type star shaped block copolymer, (PCL-PCHO)4. All the polymers prepared were characterized by different spectral and analytical methods and their thermal behaviors were investigated.

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Acknowledgements

The authors would like to thank Harran University, Scientific Research Council (HÜBAK) (Project no: 16054) for financial support and Prof Dr. Mustafa Degirmenci for the fruitful discussions during the experiments and the preparation of this paper.

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  1. Science Faculty, Department of Chemistry, Harran University, 63290, Şanlıurfa, Turkey

    Zafer Uyar & Adile Öncel

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  1. Zafer Uyar
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  2. Adile Öncel
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Correspondence to Zafer Uyar.

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Uyar, Z., Öncel, A. Preparation of a star-type telechelic macrophotoinitiator of poly(ε-caprolactone) and its use in photoinduced free radical promoted cationic polymerization. J Polym Res 25, 245 (2018). https://doi.org/10.1007/s10965-018-1638-8

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  • DOI: https://doi.org/10.1007/s10965-018-1638-8

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