Current Tröger's Base Chemistry

  title={Current Tr{\"o}ger's Base Chemistry},
  author={B. Dolensk{\'y} and J. Elguero and V. Král and C. Pardo and Martin Val{\'i}k},
  journal={Advances in Heterocyclic Chemistry},
Publisher Summary This chapter summarizes Troger's bases (TBs). It describes its historical developments, revival, synthesis and mechanism of formation, reactivity, physicochemical properties, and its uses and applications. The chapter also provides a brief discussion about pseudo-TBs. It is observed that in principle, any aromatic or heteroaromatic amine can serve as a possible precursor of TBs. TB derivatives are generally viewed as anomalous chiral substances with two nitrogen-containing… Expand
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Two flexible Tröger's base ditopic receptors C4TB and C5TB incorporating monoaza crown ether were designed and synthesized for bisammonium ion complexation and showed the highest affinity for the receptors. Expand
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Serial tris-Troger’s base derivatives (trisTBs) are members of a recently introduced family of chiral molecular clips. Naphthalene tris-Troger’s base is prepared via both stepwise and one-potExpand
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Abstract A major stumbling block in the applications of enantiomerically pure Troger's base analogues is their poor availability. We have therefore developed a facile method for the enantioseparationExpand
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Despite their continuously growing preparation and applications in the last few decades, the photophysical properties of Troger's bases (TBs) with small substituents have not been analyzed. WeExpand
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Evaluation of the anticancer activity of these agents using seven cancer cell lines and two healthy cell lines found that several derivatives had potent anticancers activity and excellent selectivity indexes toward cancer cells. Expand
Innovative Multipodal Ligands Derived from Tröger's Bases for the Sensitization of Lanthanide(III) Luminescence.
The geometry and the substitution pattern of the ligands allow the control of the stoichiometry of the species formed and the Tb(III) luminescence sensitization efficiency, showing that para -substitution patterns are more efficient than meta - Substitution ones for the formation of coordination compounds with lower T b(III)/ligand ratio. Expand
Structures of alkyl-substituted Tröger's base derivatives illustrate the importance of Z' for packing in the absence of strong crystal synthons.
Crystal structures of Tröger's base analogues with the methyl groups replaced by ethyl, iso-propyl and tert-butyl groups were studied and the incidence of Z' > 1 structures increases to rather conspicuous levels. Expand
Synthesis, Chiral Resolution, and Absolute Configuration of Functionalized Tröger’s Base Derivatives: Part II
Seven racemic derivatives of Troger’s base—the 1,7-dibromo-substituted derivative 3, the 2,8-dibromo-substituted derivative 4, the 2,8-diiodo-substituted derivative 5, the 3,9-diiodo-substitutedExpand
Efficient Intersystem Crossing in Tröger's Base Derived From 4-Amino-1,8-Naphthalimide and Application as Potent PDT Reagent.
Intersystem crossing (ISC) was observed for naphthalimide-derived Tröger's base, and the ISC is confirmed as spin orbital charge transfer ISC (SOCT-ISC) mechanism. Conventional electronExpand


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Preparation of Troger Base Derivatives by Cross-Coupling Methodologies
Derivatives of the Troger base are finding increasing application in supramolecular chemistry: they are introduced as rigid scaffolds into synthetic receptors and 'molecular torsional balances' toExpand
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Synthesis of functionalized chiral carbocyclic cleft molecules complementary to Tröger's base derivatives.
The synthesis of optically pure functionalized cleft molecules derived from dibenzobicyclo[b,f][3.3.1]nona-5a,6a-diene-6,12-dione is reported. These clefts are reminiscent of Tröger's base butExpand
Enantioselective Tröger's Base Synthetic Receptors☆
Abstract Synthetic receptors selective for the enantiomers of Troger's base ( 1 ), a compound containing chiral nitrogen atoms, have been prepared by the molecular imprinting of 1 in methacrylicExpand
A DFT study of the geometric, magnetic NMR chemical shifts and optical rotation properties of Tröger’s bases
Abstract A DFT computational study of Troger’s bases and related compounds (TBs) has been used to satisfactorily explain their geometry (including the flexibility aspect), the 1 H NMR chemical shiftsExpand
The synthesis and characterization of all diastereomers of a linear symmetrically fused Tris-Tröger's base analogue: new chiral cleft compounds.
Each of the diastereomers 1 a-c is resistant to inversion at the stereogenic nitrogen atoms under strongly and weakly acidic conditions in the range from room temperature to 95 degrees C, which is unique for analogues of Tröger's base in general to date. Expand
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Abstract Fourteen amino heterocycles were allowed to react in the different experimental conditions of formation of Troger's bases. Amino-azoles and -benzazoles yielded the corresponding Troger'sExpand
A New Entry to Bis‐Tröger’s Bases
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