Neutral [2]catenanes from oxidative coupling of π-stacked components

Induced‐Fit Binding of π‐Electron‐Donor Substrates to Macrocyclic Aromatic Ether Imide Sulfones: A Versatile Approach to Molecular Assembly

“…[8,9] This type of chemistry has also enabled the fabrication of nanoscale devices, including light-and redox-driven switches and, most recently, molecular logic gates. [10,11] A second important group of p-electron-accepting receptors, developed by Sanders et al, [12] is based on aromatic diimides, especially pyromellitic and naphthalene-tetracarboxylic diimides. Neutral catenanes and rotaxanes were obtained by templated self-assembly of aromatic diimides with 1,5-dialkoxynaphthalene derivatives.…”

“…Neutral catenanes and rotaxanes were obtained by templated self-assembly of aromatic diimides with 1,5-dialkoxynaphthalene derivatives. [12] This type of donor-acceptor interaction has also recently been used to direct the supramolecular assembly of arenes with Abstract: Novel macrocyclic receptors that bind electron-donor aromatic substrates through p-stacking donor-acceptor interactions are obtained by cycloimidisation of an amine-functionalised aryl ether sulfone with pyromellitic and 1,4,5,8-naphthalenetetracarboxylic dianhydrides. These macrocycles can form complexes with a wide variety of p-donor substrates, including tetrathiafulvalene, naphthalene, anthracene, pyrene, perylene and functional derivatives of these polycyclic hydrocarbons.…”

“…The transannular distance across the macrocycle, between the centroids of the biphenyl and diimide units, is 7.33 , again a very substantial ( % 11 %) reduction from the value of 8.19 found Figure 7. Crystal structure of 1:1 complex 4·12 between macrocycle 4 and TTF (12). Van der Waals surface contacts clearly indicate a close association between the two components, but the site-occupancy of 12 in the crystal is only % 70 %, which suggests a relatively weak free energy of binding.…”

A Catenane Assembled through a Single Charge‐Assisted Halogen Bond

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Interlocked molecules have captured chemists imagination owing to their nontrivial topology and the promise of their potential nanotechnological uses as molecular machines [1] and in chemical sensor applications.[2] The synthesis of such sophisticated architectures is a challenge, and as a consequence this has necessitated the implementation of imaginative cation, [3] anion, [4] and neutral [5] templation methodologies, which use a combination of complementary Lewis acid-base, electrostatic, and hydrogen-bonding interactions for component assembly. Halogen bonding (XB) is the attractive highly directional, noncovalent interaction between an electron-deficient halogen atom and a Lewis base.

[6] The scope of XB in solid-state crystal engineering has been intensively explored for a number of years, [7] however, in spite of the complementary analogy to ubiquitous hydrogen bonding, it is only in recent times that investigations into the application of solution-phase XB interactions to molecular recognition processes, self-assembly, and catalysis have resulted in this field developing rapidly.

[8] Indeed, in conjunction with anion templation, we have used XB to assemble interpenetrated and interlocked molecular frameworks.

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“…[2] The synthesis of such sophisticated architectures is a challenge, and as a consequence this has necessitated the implementation of imaginative cation, [3] anion, [4] and neutral [5] templation methodologies, which use a combination of complementary Lewis acid-base, electrostatic, and hydrogen-bonding interactions for component assembly. Halogen bonding (XB) is the attractive highly directional, noncovalent interaction between an electron-deficient halogen atom and a Lewis base.…”