Synthesis of tris((3-isoquinolyl)methyl)amine and bis((2-pyridyl)methyl)-(3-isoquinolyl)methylamine

Zinc-Specific Fluorescent Response of Tris(isoquinolylmethyl)amines (isoTQAs)

“…Ligand Synthesis. 1-IsoTQA and 3-isoTQA 62 were synthesized from corresponding chloromethylisoquinolines via Gabriel amine synthesis followed by N-alkylation with 2 equiv of chloromethylisoquinoline (Scheme 1). All new compounds were characterized by 1 H and 13 C NMR, and the purity of the final compounds was ensured by elemental analysis.…”

“…In this article, we report the zinc-induced fluorescence enhancement of isoquinoline derivatives of TQA, 1- and 3-isoTQA (tris­(1- or 3-isoquinolylmethyl)­amines) (Chart ). 3-IsoTQA has been prepared by Canary and co-workers and its zinc-binding property was investigated by ESI-MS; however, no fluorescent response toward zinc has been reported to date. This article reports the synthesis and evaluation of the fluorescent properties of 1- and 3-isoTQA as a new scaffold for fluorescent zinc sensor molecules.…”

Tridentate Coordination of Monosubstituted Derivatives of the Tris(2-pyridylmethyl)amine Ligand to FeCl3: Structures and Spectroscopic Properties of ((2-Bromopyridyl)methyl)bis- (2-pyridylmethyl)amine FeIIICl3 and (((2-p- Methoxyphenyl)pyridyl)methyl)Bis(2-pyridyl- methyl)]amine FeIIICl3 and Comparison with the Bis(2-pyridylmethyl)]amine FeIIICl3 Complex

“…Substituted TPA are known, although at present very little information has been reported about stable ferric monomers of functionalized ligands in that family. − We believe that the introduction of functional groups might induce noticeable change in the structure and reactivity of the iron complexes. , Thus, in view of future developments of TPA-based iron systems with functional groups, we have prepared and studied robust chloroferric complexes in which the metal is coordinated to a TPA ligand monosubstituted in the α position of one pyridyl arm by a bulky bromine atom or a methoxyphenyl ring. We have found that the steric hindrance provided by the α-substituted arm pushes it away from the coordination site, leaving it free and potentially reactive.…”

Tris(8-methoxy-2-quinolylmethyl)amine (8-MeOTQA) as a highly fluorescent Zn2+probe prepared by convenient C3-symmetric tripodal amine synthesis

“…14 In spite of its simple structure with C 3 -symmetry, previously reported preparation methods of TPA derivatives frequently adopt multistep reaction via primary amine synthesis. 1,11,[15][16][17][18][19] Although several one-step syntheses of TPA or tribenzylamine (TBA) derivatives from corresponding benzyl halides [20][21][22] or benzyl alcohol 23,24 utilizing ammonia or urea as nitrogen sources have been reported, they require transition metal catalysts such as Ru or Ir, high reaction temperature (∼140 °C) or high pressure (∼60 psi) with prolonged reaction period (12 hours-1 week), resulting in low yield in several cases. There is a great need for convenient and efficient synthesis of TPA derivatives under mild conditions such as ambient pressure and moderate temperature, use of common organic solvents (bp = ∼80 °C for conventional removal via evaporation), short reaction period and easy work-up.…”