This chapter describes the molecular designing of persistent and high-spin organic polyradicals. An unpaired electron or a spin source, which is to be introduced into the π-conjugated backbone, should be carefully selected from the list of radical species to provide both a sufficient spin-exchange interaction and chemical stability of the unpaired electrons. It is found that besides the selection of the radical species, the choice of the backbone skeleton is also crucial to produce a high-spin alignment. It is observed that as an extension of the diradical 5+, the pendant-type poly(aminium cationic radical)s based on poly(l,2-phenylenevinylene), 6+ were synthesized with well-defined chemical structures. The 3,5-bis(3,5-bis(benzyloxy)benzyloxy) benzyloxy group was selected as the dendron moiety and prepared using a convergent approach through the Willianson reaction. It is found that some of the high-spin organic polyradicals are reversibly oxidized and reduced electrochemically, which has been recently successfully employed as the electrode active material of rechargeable batteries.
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