A polyaromatic nanocapsule as a sucrose receptor in water

Abstract

A supramolecular capsule with a polyaromatic shell binds d-sucrose from natural saccharide mixtures with perfect selectivity.

Plasmonic Detection of Carbohydrate‐Mediated Biological Events

“…[39] The chemistry of saccharides and related molecules is involved in the metabolic pathways of living organisms. Due to the high number of hydroxyl groups in their structure, saccharides have high solvation enthalpies, [43,44] and are also hard to distinguish from an aqueous solvent. An obvious example is monitoring of blood glucose levels, which is of paramount importance because the breakdown of glucose transport has been correlated with diseases such as diabetes, cystic fibrosis, and cancer.…”

Hydrophilic Oligo(lactic acid)s Captured by a Hydrophobic Polyaromatic Cavity in Water

“…Nevertheless,h erein we report that the hydrophobic cavity of apolyaromatic capsule,formed through coordination-driven self-assembly,c an encapsulate hydrophilic oligo(lactic acid)s in water with relatively high binding constants (up to K a = 3 10 5 m À1 ). [5] This unusual finding stimulated us to explore the host capability of 1 toward hydrophilic and labile biologically relevant oligomers,o ligo(lactic acid)s, which so far could not be bound by previously developed synthetic cages and capsules in water. [1] There are al arge number of reports on molecular cages and capsules possessing hydrophobic cavities to efficiently bind hydrophobic molecules in water, predominantly through hydrophobic effects.…”

“…[1] There are al arge number of reports on molecular cages and capsules possessing hydrophobic cavities to efficiently bind hydrophobic molecules in water, predominantly through hydrophobic effects. [5] This unusual finding stimulated us to explore the host capability of 1 toward hydrophilic and labile biologically relevant oligomers,o ligo(lactic acid)s, which so far could not be bound by previously developed synthetic cages and capsules in water. [3] We recently found by chance that molecular capsule 1 (Figure 1b), [4] which has ahydrophobic cavity fully surrounded by multiple polyaromatic panels,e nables the selective encapsulation of hydrophilic and water-stable d-sucrose from am ixture of natural disaccharides in water.…”

“…[2] However, hydrophilic bio-oligomers comprising,f or example,a mino acids with polar side chains,nucleic acids,and saccharides are entirely hydrated in water (Figure 1a,l eft), and thus most previously reported hydrophobic cavities hardly or weakly interact with these substrates in aqueous media. [5] This unusual finding stimulated us to explore the host capability of 1 toward hydrophilic and labile biologically relevant oligomers,o ligo(lactic acid)s, which so far could not be bound by previously developed synthetic cages and capsules in water. [5] This unusual finding stimulated us to explore the host capability of 1 toward hydrophilic and labile biologically relevant oligomers,o ligo(lactic acid)s, which so far could not be bound by previously developed synthetic cages and capsules in water.…”

Self‐Assembly Process of a Pd2L4 Capsule: Steric Interactions between Neighboring Components Favor the Formation of Large Intermediates

“…[2g] Previous-ly,t he self-assembly process of aP d 2 L 4 cage composed of rigid, bent ditopic ligand 2 (Figure 1) was investigated by QASAP,w here it wasf ound that the Pd 2 2 4 cage was mainly produced from intermediates smaller than the cage and that the intramolecular ligand exchanges are represented by Pd 2 2 4 Py* 2 !Pd 2 2 4 Py* + Py* (where Py* is 3-chloropyridine, as an easily displaced ligand)a nd Pd 2 2 4 Py*!Pd 2 2 4 + Py* as the rate-determining steps in the self-assembly. [4] The molecular structure of the Pd 2 1 4 capsule indicates that the anthracene panels in the capsulea re placed in close proximity,i mplyingt hat molecular interactions between the anthracene panels would affect the self-assembly process. [3] In the Pd 2 2 4 cage, all the four bent ligandsa re apart from each other,s uggestingn oi nteraction between the bent ligands, 2.O nt he other hand, ad itopic ligand 1 (Figure 1), where the two ethynylene groups in 2 are replaced with anthracene panels,i sg eometrically quite similar to 2,b ut upon complexation with Pd II ions, the resulting Pd 2 1 4 capsulee xhibited special encapsulation properties arisingf rom accumulation of the anthracene panels to create an inner space surrounded by p-surfaces.…”