Megalo-Cavitands: Synthesis of Acridane[4]arenes and Formation of Large, Deep Cavitands for Selective C70 Uptake

Deep cavitands, concave molecular containers, represent an important supramolecular host class that has been explored for a variety of applications ranging from sensing, switching, purification and adsorption to catalysis. A major limitation in the field has been the cavitand volume that is restricted by the size of the structural platform utilized (diameter approx. 7 Å). We here report the synthesis of a novel, unprecedentedly large structural platform, named acridane[4]arene (diameter approx. 14 Å), suitable for the construction of cavitands with volumes of up to 814 Å3. These megalo-cavitands serve as size-selective hosts for fullerenes with mM to sub-μM binding affinity for C60 and C70. Furthermore, the selective binding of fullerene C70 in the presence of C60 was demonstrated

Xanthene[n]arenes: Exceptionally Large, Bowl-Shaped Macrocyclic Building Blocks Suitable for Self-Assembly

A new class of macrocycles denoted as "xanthene[ n ]arenes" was synthesized. In contrast to most other macrocycles, they feature a conformationally restricted bowl shape due to the attached alkyl groups at the linking methylene units. This facilitates the synthesis of cavitands and the self-assembly to molecular capsules via noncovalent interactions. The derivatization potential of the novel macrocycles was demonstrated on the xanthene[3]arene scaffold. Besides a deep cavitand and an oxygen-embedded zigzag hydrocarbon belt[12]arene, a modified macrocycle was synthesized that self-assembles into a hydrogen-bonded tetrameric capsule, demonstrating the potential of xanthene[ n ]arenes as a new set of macrocyclic building blocks

Xanthene[n]arenes: Exceptionally Large, Bowl-shaped Macrocyclic Building Blocks Suitable for Self-Assembly

A new class of macrocycles denoted as “xanthene[n]arenes” was synthesized. In contrast to most other macrocycles, they feature a rigid bowl-shape, required for the synthesis of cavitands and for the self-assembly to molecular capsules via non-covalent interactions. The derivatization potential of the novel macrocycles was demonstrated on the xanthene[3]arene scaffold. Beside a deep cavitand, a modified macrocycle was synthesized that self-assembles into a hydrogen-bonded tetrameric capsule. Both supramolecular systems display host-guest binding properties, demonstrating the potential of xanthene[n]arenes as a new set of macrocyclic building blocks.</div

Megalo-Cavitands: Synthesis of Acridane[4]arenes and Formation of Large, Deep Cavitands for Selective C70 Uptake

Deep cavitands, concave molecular containers, represent an important supramolecular host class that has been explored for a variety of applications ranging from sensing, switching, purification and adsorption to catalysis. A major limitation in the field has been the cavitand volume that is restricted by the size of the structural platform utilized (diameter approx. 7 Å). We here report the synthesis of a novel, unprecedentedly large structural platform, named acridane[4]arene (diameter approx. 14 Å), suitable for the construction of cavitands with volumes of up to 814 Å3. These megalo-cavitands serve as size-selective hosts for fullerenes with mM to sub-μM binding affinity for C60 and C70. Furthermore, the selective binding of fullerene C70 in the presence of C60 was demonstrated.ISSN:1433-7851ISSN:1521-3773ISSN:0570-083

Xanthene[n]arenes: Exceptionally Large, Bowl Shaped Macrocyclic Building Blocks Suitable for Self-Assembly

A new class of macrocycles denoted as "xanthene[n]arenes" was synthesized. In contrast to most other macrocycles, they feature a conformationally restricted bowl shape due to the attached alkyl groups at the linking methylene units. This facilitates the synthesis of cavitands and the self-assembly to molecular capsules via noncovalent interactions. The derivatization potential of the novel macrocycles was demonstrated on the xanthene[3]arene scaffold. Besides a deep cavitand and an oxygen-embedded zigzag hydrocarbon belt[12]arene, a modified macrocycle was synthesized that self-assembles into a hydrogen-bonded tetrameric capsule, demonstrating the potential of xanthene[n]arenes as a new set of macrocydic building blocks.ISSN:2691-370