Closely-spaced chelating centers: synthesis of novel spiro-bridged bis-phenanthrolines and bis-indole derivatives

✍ Scribed by Feiyue Wu; Elvira C. Riesgo; Randolph P. Thummel; Alberto Juris; Muriel Hissler; Abdelkrim El-ghayoury; Raymond Ziessel

• Publisher: Elsevier Science
• Year: 1999
• Tongue: French
• Weight: 248 KB
• Volume: 40
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(99)01413-6

✦ Synopsis

The syntheses of novel soluble ditopic 1,10-phenanthroline ligands bearing a central spiro-[5.5]undecane or a spiro-[5.5]bifluorylidene fragment are reported. The synthetic approach is based on a Friedl~inder condensation between 8-amino-7-quinolinecarbaldehyde and either 3,9-diketospiro-[5.5]undecane or 2,2'-diacetylspiro[5.5]bifluorylidene derivatives. Reaction of the latter with phenylhydrazine and subsequent cyclization afforded 2,2'-di-(2"-indolyl)-[5.5]spirobifluorylidene. The photophysical properties of the new compounds are briefly discussed and Ru(II) and Cu(I) complexes were prepared.