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A series of water soluble octa-functionalized POSSs were facilely synthesized via thiol ene and Menschutkin click chemistry.Among them, octa-alkynyl POSS further reacted with azide-terminal alkyl long chains, resulting in a well-defined, amphiphilic octopus-like POSS.For the first time it was used for host-guest encapsulation and it exhibited an ultrahigh loading capability.