Synthesis and Properties of a Cyclohexa‐2,7‐anthrylene Ethynylene Derivative

Abstract

The synthesis of a cyclohexa‐2,7‐(4,5‐diaryl)anthrylene ethynylene (1) was achieved for the first time by using 1,8‐diaryl‐3,6‐diborylanthracene and 1,8‐diaryl‐3,6‐diiodoanthracene as key synthetic intermediates. Macrocycle 1 possesses a planar conformation of approximately D6h symmetry, because of the triple‐bond linker between the anthracene units at the 2,7‐positions. It was confirmed that macrocycle 1, bearing bulky substituents at the outer peripheral positions, behaves as a monomeric form in solution without π‐stacking self‐association. Macrocycle 1 has an inner‐cavity size that allows specific inclusion of [9]cycloparaphenylene ([9]CPP), but not [8]CPP or [10]CPP, through an aromatic edge‐to‐face CH‐π interaction.

Structures and Supramolecular Properties of Inclusion Complexes of Anthracene‐Triptycene Nanocages with Fullerene Guests and Their Dynamic Motion as Molecular Gyroscopes

“…Among such noncovalent interactions, CH⋅⋅⋅π interactions [2,3] play an important role in the structures of organic crystals [4] and biomolecules [5] . However, supramolecular complexes associated mainly by CH⋅⋅⋅π interactions are rare because these interactions are weak and sensitive to the direction and distance of interacting moieties [2c,6,7] . Therefore, host‐guest systems driven by CH⋅⋅⋅π interactions need to be designed to maximize overall association energies in a precise manner.…”

Composition‐selective full inclusion host–guest interaction of azobenzene‐containing photoresponsive nanoring with fullerene C60

“…Currently, the development of host‐guest systems involving fullerenes has attracted much attention for chemical sensor, 1,2 supramolecular and electric materials, 3,4 nanoscale mechanics 5,6 and separation of specific fullerenes 7 . Carbon nanorings (CNRs) 8–14 and ligand–metal ring are two most popular hosts for fullerenes 15,16 . It is known that the selective and efficient encapsulation for the fullerene guests is an essential property in design of stable host‐guest supramolecular systems.…”

Synthesis, Structures, and Complexation with Phenolic Guests of Acridone‐Incorporated Arylene–Ethynylene Macrocyclic Compounds

“…reported such a compound having three 2,7‐anthrylene units at alternating positions, which underwent self‐assembly in a solution or in the solid state [5] . Recently, they synthesized an all 2,7‐anthrylene macrocycle, which included a [9]cycloparaphenylene molecule into the cavity [6] . These compounds inspired us to incorporate other aromatic units to create novel macrocycles having various properties.…”