A series of bifunctional cyclopentadienes of the type 1,3-EtOCO-HCp-linker-NH2 were synthesized. In this series, the linker length (distance
between the amine functionalities and the cyclopentadiene) has been
systematically varied (CH2)
n
(n = 1–3). The corresponding
Re complexes [(η5-C5H3RR′)Re(CO)3] (R = −COOEt, R′
= −linker–NH2) were synthesized and structurally
characterized. They exhibit extraordinary stability toward water and
air. All bifunctional cyclopentadienes have been labeled with the
[99mTc(CO)3]+ moiety. Whereas the
reactions with ethylene and propylene linked cyclopentadiene under
mild reaction conditions led to the products in high radiochemical
purity (>96%) without applying further purification protocols, harsher
reaction conditions were required for the synthesis of the methylene-linked
cyclopentadiene compound. Masking the amine in the methylene-linked
cyclopentadiene by an amide bond bypasses this problem. The very hydrophilic
characters of these complexes were assessed by K
OW analysis. The reported cyclopentadienes and their complexes
offer a robust and versatile platform for (radio)metal incorporation
into biologically active lead structures.