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. Author manuscript; available in PMC: 2011 May 12.
Published in final edited form as: Chem Rev. 2010 May 12;110(5):3212–3236. doi: 10.1021/cr900396q

Scheme 4.

Scheme 4

LiNc-BuO was synthesized from lithium metal and octa-n-butoxy-substituted naphthalocyanine (Nc-BuO) (i) in n-pentanol. Nc-BuO macrocyclic ligand reacted with lithium pentoxide (lithium metal in pentanol) to give dilithium octa-n-butoxy-naphthalocyanine (Li2Nc-BuO) (ii), followed by oxidation to give LiNc-BuO radical (iii) which formed as needle-shaped dark-green microcrystals.