Synthesis of a Tetracorannulene-perylenediimide That Acts as a Selective Receptor for C₆₀ over C₇₀

Abstract

We report the use of a tetraborylated perylenediimide as starting material for the preparation of a tetracorannulene-perylenediimide that is able to bind up to two fullerene-C60 molecules by host–guest molecular recognition with preference over C70. Titration with fullerene-C60 is followed by a dramatic shift of the aromatic signals in 1H NMR and an initial increase in the fluorescence of the system. By this simple mechanism, fluorogenic sensing of fullerene-C60 is easily accomplished by an unprecedented fluorescent turn-on mechanism.

Molecule Recognition and Release Behavior of Naphthalenediimide Derivative via Supramolecular Interactions

“…For rational molecular recognition, sufficient intermolecular interactions are required as a driving force to construct a stable multi‐component framework. Generally, binding pairs adopt a comparable size and flat conformation to generate strong coplanar π–π interactions, favoring mixed‐stacking‐type co‐assemblies [ 17–19 ] or cage‐like conformations for stable complexation, [ 20,21 ] serving as powerful design rules to form a class of organic host–guest cocrystals in a highly‐ordered hybrid arrangement via supramolecular synthesis. Furthermore, electric potential differences could lead to intermolecular charge‐transfer effects between each adjacent component molecules.…”

Octapodal Corannulene Porphyrin-Based Assemblies: Allosteric Behavior in Fullerene Hosting

“…These examples highlight the importance of the preorganization and morphology of the supramolecular platform in fullerene association, which can be as important as the number of corannulene units attached. Therefore, to increase host–guest surface contact, careful design of fullerene receptors is required in addition to increasing the number of corannulene units …”

Self-Assembly Hydrosoluble Coronenes: A Rich Source of Supramolecular Turn-On Fluorogenic Sensing Materials in Aqueous Media

“…Our synthesis started by the Suzuki reaction of the dibromoperylene­diimide 1 with two equivalents of a N -Boc protected piperazinyl-pyrimidine boronic ester 2 in conditions used for related Suzuki reactions (Figure ). , The bis-substituted, four N -Boc protected derivative 3 (85% yield) was obtained after workup of the reaction. Irradiation of 3 in dichoro­methane (DCM) under visible light (halogen lamp, 50W, 4 cm distance) and air for 7 h gave the N -Boc protected coronene 4 (89% yield).…”