3,4-Ferrocenyl-Functionalized Pyrroles: Synthesis, Structure, and (Spectro)Electrochemical Studies

Marcus Korb, Ulrike Pfaff, Alexander Hildebrandt, Tobias Rueffer, Heinrich Lang

Research output: Contribution to journalArticle

13 Citations (Scopus)

Abstract

The synthesis of 3,4-diferrocenyl-substituted pyrroles of the type 3,4-Fc(2)-cC(4)H(2)NR [Fc = Fe((5)-C5H4)((5)-C5H5); R = Ph (3a), SO2-4-MeC6H4 (Ts) (3b), SiiPr(3) (3c)], 3,4-(FcCC)(2)-cC(4)H(2)NR [R = Ph (4a), Ts (4b)], and 3-Br-4-FcCC-cC(4)H(2)NR [R = Ph (7a), Ts (7b)] from 3,4-Br-2-cC(4)H(2)NR [R = Ph (2a), Ts (2b), SiiPr(3) (2c)] is discussed. The molecular structures of 3a,b, 5, 4b, and 7b in the solid state are reported and show that the formal double bonds in the heterocyclic core are rather localized relative to pyrrole itself. The investigations with (spectro)electrochemical methods reveal the different capabilities for the formation of mixed-valent species and allows the classification of 3a,b as class II systems, whereas compounds that feature electron-withdrawing -CC- units (4a,b) can be assigned to class I systems according to Robin and Day.

Original languageEnglish
Pages (from-to)1051-1061
Number of pages11
JournalEuropean Journal of Inorganic Chemistry
Volume2014
Issue number6
DOIs
Publication statusPublished - Feb 2014
Externally publishedYes

Cite this