New 4′‐Functionalized 2,2′:6′,2′′‐Terpyridines for Applications in Macromolecular Chemistry and Nanoscience

Abstract

The well‐known reaction of 4′‐chloro‐2,2′:6′,2′′‐terpyridine with alkoxide nucleophiles leads to 4′‐functionalized 2,2′:6′,2′′‐terpyridines. This reaction allows the easy introduction of different functional groups onto the terpyridine at the 4′‐position, i.e. opposite to the metal binding site, in one reaction step. Among the functionalized 2,2′:6′,2′′‐terpyridines reported here are amines (including chiral examples), carboxylic acids, simple alkoxy‐chain terpyridines with different chain lengths, and a stilbene‐functionalized terpyridine. Moreover, the synthesis of two important already known substances was significantly improved. One example of a sequential functionalization of the (aminopentoxy)terpyridine with a dithiolane functionality is also reported. For two of the alkyl‐chain‐functionalized terpyridines, single‐crystal X‐ray crystallographic data were obtained. Finally, ordered monolayers of alkyl‐substituted terpyridines on HOPG were visualized using STM. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)

Terpyridine‐Functionalized Surfaces: Redox‐Active, Switchable, and Electroactive Nanoarchitecturesgland

“…Both the Schubert and Constable groups could show that alkoxy-functionalized terpyridines 15 and 16 ( Figure 15 a) can be assembled into highly ordered architectures on graphite surfaces. [58][59][60] The STM was utilized to study the adsorbed terpyridines at the solid/liquid interface of highly ordered pyrolytic graphite (HOPG); well-ordered 2D arrays of 15 were observed on HOPG in 1-phenyloctane (Figure 15 b). Large ( > 500 nm), well-defi ned lamellar domains could be visualized.…”

Synthesis and Characterization of a Series of Ruthenium Tris(β‐diketonato) Complexes by an UHV‐STM Investigation and Numerical Calculations

“…[21][22][23] A recent review also appeared on STM spectroscopy of magnetic molecules. [24] Several studies have been reported on ruthenium compounds measured by STM [25][26][27][28][29][30][31][32][33][34][35][36] and also on ruthenium and tris(diketonato) ligands, [37][38][39][40][41][42] but very few on adsorption of ruthenium or metal acetylacetonate (acac) complexes and their derivatives. [43,44] It is then of interest to synthesize and characterise Ru complexes including ligands that are favoured for their evaporation and adsorption for further investigations using STM and related techniques such as scanning tunnelling spectroscopy.…”

Tuning the Thermotropic and Lyotropic Properties of Liquid‐Crystalline Terpyridine Ligands

“…In particular, terpy and its multiple derivatives have been used advantageously as building blocks for the engineering of novel supramolecular structures such as spiral lines, [26] dendrimers, [27] micelles, [28] polymers, [29,30] and liquid-crystalline soft materials. [31] Formation of ordered architectures on surfaces, [32][33][34] functional molecular devices, [35] and biochemical applications [36] are particularly challenging.…”