Synthesis and evaluation of a pseudocyclic tristhiourea-based anion host.
A novel methodology for the evaluation of receptor arrangement in structurally flexible anion chemosensors was developed and applied to map the binding site of a new pseudocyclic tristhiourea chemosensor (6). The syntheses of 6 and related macrocyclic chemosensor 10 (a model of the folded monomeric structure of 6) are reported. Both chemosensors were evaluated by titration with a variety of structurally different anions in CH3Cl and DMSO, showing a common preference for F-, CH3CO2-, and H2PO4-. However, within this group of anions, the binding patterns of the chemosensors differed, indicating dissimilarity in the arrangement of the binding sites of 6 and 10.
Dahan
Adi
A
School of Chemistry, Raymond and Beverly Sackler Faculty of Exact Sciences, Tel Aviv University, Tel Aviv 69978, Israel.
Ashkenazi
Tali
T
Kuznetsov
Vladimir
V
Makievski
Svetlana
S
Drug
Eyal
E
Fadeev
Ludmila
L
Bramson
Maayan
M
Schokoroy
Sari
S
Rozenshine-Kemelmakher
Emily
E
Gozin
Michael
M
D000838:Anions / Q000737:chemistry*; D003500:Cyclization; D019281:Dimerization; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D008968:Molecular Conformation; D010777:Photochemistry; D013890:Thiourea / Q000737:chemistry*; D017186:Titrimetry
D000838:Anions; D013890:Thiourea