Abstract
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 2f has been further used as a building block for the synthesis of donor-acceptor SubPc-C60 hybrid 8, while iodo-SubPc 2e 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 2a-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.
Original language | English |
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Pages (from-to) | 7554-7562 |
Number of pages | 9 |
Journal | Chemistry - A European Journal |
Volume | 16 |
Issue number | 25 |
DOIs | |
Publication status | Published - 2010 Jul 5 |
Keywords
- Fluorine
- Phthalocyanines
- Porphyrinoids
- Substitution reaction
- Synthesis
ASJC Scopus subject areas
- Catalysis
- Organic Chemistry