Nathan L Strutt

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A template-directed protocol, which capitalizes on donor-acceptor interactions, is employed to synthesize a semi-rigid cyclophane (ExBox(4+)) that adopts a box-like geometry and is comprised of π-electron-poor 1,4-phenylene-bridged ("extended") bipyridinium units (ExBIPY(2+)). ExBox(4+) functions as a high-affinity scavenger of an array of different(More)
Macrocyclic chemistry has relied on the dominance of some key cavitands, including cyclodextrins, calixarenes, cyclophanes, and cucurbiturils, to advance the field of host-guest science. Very few of the many other cavitands introduced by chemists during these past few decades have been developed to near the extent of these four key players. A relatively new(More)
Alkanediamines serve as neutral guests for the recently discovered host pillar[5]arene. The proposed [2]pseudorotaxane nature of the superstructure of the 1:1 host-guest complexes is supported by the template-directed synthesis of a related [2]rotaxane. A synthetic route to monofunctional pillar[5]arenes has also been developed, allowing for the creation of(More)
Stacking on a full belly: Triangular molecular prisms display electron sharing among their triangularly arranged naphthalenediimide (NDI) redox centers. Their electron-deficient cavities encapsulate linear triiodide anions, leading to the formation of supramolecular helices in the solid state. Chirality transfer is observed from the six chiral centers of(More)
After the manner in which coenzymes often participate in the binding of substrates in the active sites of enzymes, pillar[5]arene, a macrocycle containing five hydroquinone rings linked through their para positions by methylene bridges, modifies the binding properties of cucurbit[6]uril, such that the latter templates azide-alkyne cycloadditions that do not(More)
Stereoelectronic complementarity between the active site of an enzyme and the transition state of a reaction is one of the tenets of enzyme catalysis. This report illustrates the principles of enzyme catalysis (first proposed by Pauling and Jencks) through a well-defined model system that has been fully characterized crystallographically, computationally(More)
We announce the establishment of a new family of macrocycles--the asararenes, which are based on para-methylene linked "asarol methyl ether" (1,2,4,5-tetramethoxybenzene) units. Macrocycles with 6-12 aromatic units have been synthesized and isolated in a single step from asarol methyl ether and paraformaldehyde. Even larger rings, with up to 15 asarol(More)
A series of regioselective di- and trifunctionalized pillar[5]arene derivatives have been synthesized by a deprotection-followed-by-activation strategy, and their constitutions have been established as a result of having access to their solid-state structures. De-O-methylation occurs in a stepwise manner at lower temperatures under kinetic control,(More)