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Trifluoroethoxy‐Coating Improves the Axial Ligand Substitution of Subphthalocyanine
Author(s) -
Shibata Norio,
Das Banibrata,
Tokunaga Etsuko,
Shiro Motoo,
Kobayashi Nagao
Publication year - 2010
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201000373
Subject(s) - substitution (logic) , coating , ligand (biochemistry) , chemistry , materials science , composite material , computer science , biochemistry , receptor , programming language
A novel trifluoroethoxy (TFEO)‐coated SubPc ( 1 ) and various axially functionalised derivatives thereof ( 2 ) have been efficiently synthesised. The advantage of the TFEO‐coating on SubPcs compared to conventional fluorine‐coated or uncoated molecules has been clearly demonstrated, as axial derivatisation has been realised in very good yields. Among various SubPcs synthesised, formyl‐SubPc 2 f has been further used as a building block for the synthesis of donor–acceptor SubPc–C 60 hybrid 8 , while iodo‐SubPc 2 e has been used for the synthesis of trifluoroethoxy‐coated SubPc–Pc dyads 9 and 10 . All of these compounds are highly soluble in all common organic solvents, which greatly facilitates their purification and characterisation. The SubPcs 2 a – c incorporating oligoethylene glycol moieties are attractive from a biological point of view, while SubPcs 8 – 10 may prove useful for studies of intramolecular electron‐ and energy‐transfer processes.