Thiourea Derived Tröger’s Bases as Molecular Cleft Receptors and Colorimetric Sensors for Anions

Abstract

Thiourea-functionalized Tröger's base receptors 1 and 2 have been synthesized and evaluated as novel for the recognition of anions. Receptor 2 gave rise to significant changes in the absorption spectrum upon titration with AcO(-) and H2PO4(-) and acted as a colorimetric sensor for F(-), the interaction of which was also evaluated using (1)H NMR spectroscopy.

Efficient Intersystem Crossing in the Tröger's Base Derived From 4‐Amino‐1,8‐naphthalimide and Application as a Potent Photodynamic Therapy Reagent

“…Concerning the EC 50 value, NI‐TB is also more potent than the iodinated cyanine triplet PSs (EC 50 =25 μ m ) and brominated Bodipy sensitizers . The potent PDT activity of NI‐TB may be attributed to its tight binding ability with DNA . The preparation of Tröger's bases showing red and near‐IR light absorption is in progress.…”

Anion Receptor Chemistry

“…The authors proposed that Trö ger's base is a rigid scaffold that contains two aryl rings almost perpendicular to each other. Boyle et al 9 used this scaffold to preorganize two thiourea groups for the binding and sensing of anions. Receptors 19 and 20 ( Figure 5) were found to form 1:1 and 1:2 (receptor:anion) hydrogen-bond complexes with dihydrogenphosphate and acetate in DMSO, and interestingly neither of them bound sulfate.…”

Diastereoselective Self‐Assembly of a Neutral Dinuclear Double‐Stranded Zinc(II) Helicate via Narcissistic Self‐Sorting

“…The unique shape and the N-centered chirality of Trçger's base has been fascinating chemists for more than ac entury now, [1] and thus, this scaffoldh as found numerous applicationsi n many different areas such as medicinal chemistry, [2] optoelectronics, [3] as ligandsf or transition metal catalysts, [4] as microporous polymers, [5] as chiral auxiliaries, [6] or in supramolecular chemistry. [7] Based on Wärnmark's versatile protocol for the preparation of functionalized Trçger's base derivativess tarting from simple functionalized anilines, [8] we have also made some contributions to this field by synthesizingn ew derivatives and achieving their chiral resolution via HPLC on chiral stationary phases, [9] and the Trçger'sb ase scaffold turned out to be at ruly privileged V-shaped structuralm otif for the formation of stereochemically well-definedm etallosupramolecular aggregates in our hands. [10][11][12] So far,w eh ave synthesized ligandsb ased on the Trçger's base backbonew hich have pyridylimine, [10a] 2,2'-bipyridyl, [10] catechol, [11] nitrile, [12a] or pyridine [12b] groups as coordinating groups that give rise to cationic or anionic oligonuclear coordination compounds.…”