Binding of the terephthalate dianion by di- tri- and tetrathiourea functionalised fused [3] and [5]polynorbornane based hosts.
The affinity of new di-, tri- and tetrathiourea functionalised fused [3] and [5]polynorbornane based hosts 1-6 towards terephthalate2- was proportional to the size of the preorganised cleft/cavity imparted by the polynorbornane scaffold. Receptors based on the [5]polynobornane framework had greater affinities for the anion due to a higher degree of host:guest size complementarity. Hosts 1-5 formed 1:1 host:guest complexes with the rigid dianion, yet remarkably, host 6 was found to bind two terephthalate guests.
Lowe
Adam J
AJ
School of Life and Environmental Sciences, Deakin University, Geelong, VIC, Australia.
Pfeffer
Frederick M
FM
D001892:Camphanes / Q000737:chemistry*; D006860:Hydrogen Bonding; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D008968:Molecular Conformation; D010795:Phthalic Acids / Q000737:chemistry*; D013890:Thiourea / Q000737:chemistry*
D001892:Camphanes; D010795:Phthalic Acids; C032279:phthalic acid; D013890:Thiourea