Synthesis of Water-Soluble Chiral DOTA Lanthanide Complexes with Predominantly Twisted Square Antiprism Isomers and Circularly Polarized Luminescence.

One-step cyclization of a tetraazamacrocycle 5 with 70% yield in a 25-g scale was performed. Its chiral DOTA derivatives, L4, has ∼93% of TSAP coordination isomer in its Eu(III) and Yb(III) complexes in aqueous solution. [GdL4]5- exhibits a high relaxivity, making it a promising and efficient MRI contrast agent. High luminescence dissymmetry factor (glum) values of 0.285 (ΔJ = 1) for [TbL3]- and 0.241 (ΔJ = 1) for [TbL4]5- in buffer solutions were recorded.