Computational chemistry

Chemistry

Materials science

Conjugated system

Chemical physics

Ambipolar diffusion

Physics

Crystallography

Nanotechnology

Organic chemistry

HOMO/LUMO

Aromaticity

Quantum mechanics

Molecule

Plasma

Supramolecular chemistry

Fullerene

Trimer

Dimer

Polymer

Antiaromaticity

Journal of the American Chemical Society

Conjugated nanohoops provide a platform to study structure-property relationships; they are attractive hosts for supramolecular chemistry as well as promising candidates as new organic materials. We herein present [n]cyclodibenzopentalenes ([n]CDBPs) as antiaromatic analogues of [n]cycloparaphenylenes. Platinum-mediated macrocyclization of dibenzopentalene boronic esters provided the trimer and tetramer with strain energies of up to 80 kcal mol-1. In the solid state, the cylindrical [4]CDBP molecules align to form columnar structures. The larger hoop [4]CDBP binds both fullerenes C60 and C70 with temperature-dependent exchange behavior, providing higher activation energies for the exchange compared to [10]CPP. The antiaromatic character of the [n]CDBPs paired with the cyclic conjugation leads to high HOMO energies and lowered LUMO energies with band gaps below 2 eV. This work presents a new class of the antiaromatic and nonalternant curved nanocarbons with intriguing supramolecular and ambipolar optoelectronic properties.

[<i>n</i>]Cyclodibenzopentalenes as Antiaromatic Curved Nanocarbons with High Strain and Strong Fullerene Binding

[n]Cyclodibenzopentalenes as Antiaromatic Curved Nanocarbons with High Strain and Strong Fullerene Binding