Towards allosteric receptors – synthesis of β-cyclodextrin-functionalised 2,2’-bipyridines and their metal complexes

Abstract

SummaryHerein, we present three new 2,2’-bipyridines that carry two β-cyclodextrin moieties in different substitution patterns. When coordinated by zinc(II) or copper(I) ions (or their complexes), these compounds undergo conformational changes and switch between “open” and “closed” forms and thereby bringing together or separating the cyclodextrin moieties from each other.

Curing Behavior of Waterborne Paint Containing Catalyst Encapsulated in Micelle

“…A catalyst that remains functionally inactive at temperatures of 40 • C or lower and activates at temperatures of 100 • C or higher is called a switchable catalyst. A wide range of technologies have been reported to realize these catalytic switching properties, including encapsulating the catalyst in compounds such as cyclodextrin [9][10][11][12][13][14][15][16]. For instance, Wang et al reported smart supramolecular nano-enzymes with temperature-driven switching properties have been successfully constructed by the selfassembly of supra-amphiphiles formed by the cyclodextrin-based host-guest chemistry [9].…”

Kinetics and Thermodynamics of Constitutional Dynamic Coordination Systems Based on FeII, CoII, NiII, CuII, and ZnII

“…Zinc(II) triflate [Zn(OTf) 2 ] and iron(II) perchlorate [Fe(ClO 4 ) 2 ] were chosen as suitable metal sources for the dynamic complexes, owing to their favorable solubility properties in methanol. Two different ligands were in addition chosen: 5,5′‐ and 4,4′‐substituted 2,2′‐bipyridines, expected to display relatively minor structural differences of the different complexes compared to the 3,3′‐ or 6,6′‐substituted counterparts . Crystal structures have been reported for some of the homoleptic complexes .…”

“…Two different ligands were in addition chosen: 5,5′-and 4,4′-substituted 2,2′-bipyridines, expected to display relatively minor structural differences of the different complexes compared to the 3,3′-or 6,6′-substituted counterparts. [35][36][37][38] Crystal structures have been reported for some of the homoleptic complexes. [39][40][41][42][43][44][45][46][47][48] For detection purposes, 5,5′-dimethyl-2,2′-bipyridine L1 and stable, isotope-labeled ligand [D 6 ]-4,4′-dimethyl-2,2′-bipyridine L2, prepared using microwave-assisted deuteration, [49] were thus used to construct the complexes (Figure 1).…”

Allosteric Binding of Capsaicin by a Bis(β‐cyclodextrin)‐2,2′‐bipyridine Receptor

“…In a second approach, we utilized β‐cyclodextrins due to their known ability to bind a great variety of nonpolar substrates7 and their tunable solubility, which we connected to the bipyridines by thiourea moieties 8. Herein, we report the new, water‐soluble derivative 1 of these systems and its allosterically controlled binding behavior towards capsaicin.…”