Trifluoroethoxy-coating improves the axial ligand substitution of subphthalocyanine

Norio Shibata, Banibrata Das, Etsuko Tokunaga, Motoo Shiro, Nagao Kobayashi

Research output: Contribution to journalArticlepeer-review

38 Citations (Scopus)

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 languageEnglish
Pages (from-to)7554-7562
Number of pages9
JournalChemistry - A European Journal
Volume16
Issue number25
DOIs
Publication statusPublished - 2010 Jul 5

Keywords

  • Fluorine
  • Phthalocyanines
  • Porphyrinoids
  • Substitution reaction
  • Synthesis

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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