Themed collection Celebrating 200 Years of Benzene

Chemical reduction coupled with X-ray crystallographic and spectroscopic analyses reveals the electron accepting abilities of molecular nanographenes with various topological features, further supporting their advanced energy-storage applications.

Molecular nanographenes are graphene analogues at the nanoscale. Among the emerging strategies to modulate their optoelectronic properties, vertical π–π stacking between the graphitized layers has recently gained attention as a powerful tool.

Recent advances in bottom-up synthesis strategies have enabled precise control over the edge, backbone, and heterostructure of graphene nanoribbons.

Visible-light-induced oxidative cleavage of α-substituted styrenes proceeds via a methyl-radical-initiated pathway mediated by photoexcited dibenzothiophene S-oxide, enabling uniquely selective cleavage of electron-deficient styrenyl CC bonds.

Racemic and enantiopure ditriptyceno[n]helicenes (n = 5–7) were accessed via a modular, straightforward synthesis, enabling a systematic investigation of their conformational dynamics, solubility, electronic and (chir)optical properties.

The fruitful combination of nanographene and platinahelicene gives access to circularly polarized phosphorescence in the near-infrared domain.

Unexpected π-stacked dimerization of an antiaromatic homoHPHAC monocation alleviates antiaromatic destabilization in solution and the solid state.

Crystallization of hexakis((4-isopropylphenyl)thio)benzene yields two polymorphs, exhibiting distinct room-temperature phosphorescence colors due to the different molecular conformations adopted, as confirmed by quantum-chemical calculations.

Neutron total scattering of phenanthrene and pyrene, analysed by simulation based data refinement, have been compared to previous analyses from benzene and naphthalene, showing that π-stacking becomes more overlapped as aromatic size increases.

Helical chirality is integrated into overcrowded-alkene motors as the sole chiral element, and the subtle interplay of the isomerization processes that governs the resulting rotational behavior is studied for every new motor design.

Fusing antiaromatic units to other antiaromatic units could afford delocalized [4n]–[4n]–[4n] π-systems with reduced paratropicity (or even weak diatropicity), while retaining narrow HOMO–LUMO gaps.

We computationally explore strategies to stabilize boroloborinines, a rare 8π-electron antiaromatic borole–borinine scaffold, revealing design principles for photostable antiaromatic chromophores in organic electronics.

Peri-fused PAHs converge to a single localized representation: cata-condensation increases aromatic sextets and amplifies brightness while linear extension adds cis-diene units and diminishes it.

Solid-state VCD and chiral anisotropic ²H NMR spectroscopies are successfully used in the analysis of highly enantioenriched isotopically chiral atropisomers derived from enantiopure BINOL.

Annulative π-extension (APEX) reaction is a useful aromatic ring-fusion method for the synthesis of large polycyclic aromatic hydrocarbons (PAHs) from unfunctionalized small PAHs.

A versatile synthesis of benzothiophene-fused pentalenes enables late-stage diversification and reveals substituent-dependent antiaromaticity, providing a platform for designing functional antiaromatic π-electron systems.

Low-temperature synthetic route to heteroatom-doped nanographenes, enabled by molecular self-assembly.

A three-component coupling reaction was devised to synthesize a two-story cage molecule consisting of a sextuple helix. The helical structure was unexpectedly entangled to form a duodecuple helix with homohelicity.

Two successive Au-catalyzed alkyne hydroarylation events allow the assembly of trithia[5]helicenes with high enantioselectivity. The racemization barrier of the structures prepared was experimentally determined (ΔG^≠ = 35.6 kcal mol⁻¹ at 175 °C).

Magnetically induced 3D current densities, net bond current strengths and divergence of the isotropically averaged Lorentz force density are used to characterize the magnetic response of giant I_h-fullerenes containing 240 and 540 carbon atoms.

Singlet fission (SF) can improve solar-cell efficiency. We present a machine-learning workflow combining AQME, ROBERT, and DFT calculations to screen 3835 benzannulated biphenylenes, identifying 505 promising candidates for SF.

A green-emitting N-doped quadruple helicene which was prepared via a straightforward three-step route possesses a |g_lum| of 1.8 × 10⁻³.

Multivalent glyco-functionalized carbon nanodots inhibit SARS-CoV-2 trans-infection by targeting DC-SIGN and L-SIGN lectin receptors. Surface architecture and glycan presentation dictate antiviral efficacy and receptor-mediated uptake.

We report the first electron-transport study through saddle-shaped NGs, using experimental and theoretical approaches. For the studied systems, our results show that there are no significant changes in conductance, compared with the planar analogues.

The concentration of hole scavenger Na₂SO₃ in nitrobenzene photoreduction catalyzed by CdS quantum dots determines reaction selectivity, highlighting how scavenger quantity can direct photocatalytic pathways.

The conformational, (chir)optical and aromatic properties of singly and triply twisted Möbius-shaped cyclotris[5]helicenes are scrutinized.

The influence of the aromaticity, diradical character and strain on the reactivity of group 14 heavier 1,4-dimetallabenzenes (E = Si, Ge, Sn, Pb) has been investigated using quantum-chemical calculations.

Helically chiral π-expanded diindenoperylenes with dithia[7]helicene moieties were synthesized and their chiroptical properties were studied. Late-stage oxidation of the thiophenes enabled the tuning of chiroptical and electrochemical properties.

Diarylbenzodithieno[5.5.5.6]fenestranes exhibit unusual dual emission (left), but upon twofold formylation and/or oxidative cyclization (right), only monomeric emission occurs.

Triangular acenes display size-dependent radical character arising from the interplay between Clar's sextet stabilization and the release of cyclobutadiene antiaromaticity.