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Issue 8, 2012
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Fluorinated polyhedral oligomeric silsesquioxane-based shape amphiphiles: molecular design, topological variation, and facile synthesis

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Abstract

This paper reports the design and synthesis of fluoroalkyl-functionalized polyhedral oligomeric silsesquioxane (FPOSS)-based shape amphiphiles with two distinct topologies: (i) mono-tethered FPOSS-poly(ε-caprolactone) (PCL) and (ii) FPOSS tethered with two polymer chains possessing different compositions, namely, polystyrene (PS) and PCL, denoted as PS–(FPOSS)–PCL. The synthetic strategy features an efficient “growing-from” and “click-functionalization” approach. From a monohydroxyl-functionalized heptavinyl POSS, a PCL chain was grown via ring opening polymerization (ROP) of ε-caprolactone; subsequent thiol–ene “click” chemistry with 1H,1H,2H,2H-perfluoro-1-decanethiol allowed the facile introduction of seven perfluorinated alkyl chains onto the POSS head. Similarly, PS–(FPOSS)–PCL was synthesized from a PS precursor bearing both hydroxyl group and heptavinyl POSS at the ω-end, which was prepared by living anionic polymerization and hydrosilylation. The compounds were fully characterized by 1H NMR, 13C NMR, FT-IR spectroscopy, MALDI-TOF mass spectrometry, and size exclusion chromatography. The introduction of perfluorinated molecular cluster into polymers is expected to make them surface-active while the interplay between crystallization and fluorophobic/fluorophilic bulk phase separation in these shape amphiphiles shall lead to intriguing self-assembly behavior and novel hierarchical structures. This study has demonstrated FPOSS as a versatile building block in the construction of shape amphiphiles and established a general and efficient method to introduce such fluorous molecular clusters into polymers.

Graphical abstract: Fluorinated polyhedral oligomeric silsesquioxane-based shape amphiphiles: molecular design, topological variation, and facile synthesis

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Publication details

The article was received on 24 Feb 2012, accepted on 18 Apr 2012 and first published on 17 May 2012


Article type: Paper
DOI: 10.1039/C2PY20101A
Citation: Polym. Chem., 2012,3, 2112-2120
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    Fluorinated polyhedral oligomeric silsesquioxane-based shape amphiphiles: molecular design, topological variation, and facile synthesis

    J. He, K. Yue, Y. Liu, X. Yu, P. Ni, K. A. Cavicchi, R. P. Quirk, E. Chen, S. Z. D. Cheng and W. Zhang, Polym. Chem., 2012, 3, 2112
    DOI: 10.1039/C2PY20101A

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