Themed collection Emerging Frontiers in Aromaticity

31 items
Open Access Editorial

Emerging frontiers in aromaticity

This themed collection reflects on the relevance of aromaticity in modern chemistry by highlighting the most recent discoveries and views, offering a selection of articles on a wide variety of relevant subjects.

Graphical abstract: Emerging frontiers in aromaticity
From the themed collection: Emerging Frontiers in Aromaticity
Open Access Perspective

Aromaticity: Quo Vadis

In this perspective, different expert opinions are gathered on the definition and concept of aromaticity.

Graphical abstract: Aromaticity: Quo Vadis
From the themed collection: Celebrating Latin American Chemistry
Open Access Review Article

Synthesis of octagon-containing molecular nanocarbons

Nanocarbons, such as fullerenes, carbon nanotubes, and graphenes, have long inspired the scientific community.

Graphical abstract: Synthesis of octagon-containing molecular nanocarbons
From the themed collection: Emerging Frontiers in Aromaticity
Open Access Edge Article

Buckybowl and its chiral hybrids featuring eight-membered rings and helicene units

A novel buckybowl and its chiral hybrids featuring eight-membered rings and helicene units have been synthesized and characterized. The resulting hybrid and its complex with C60 show promising ambipolar transport characteristics.

Graphical abstract: Buckybowl and its chiral hybrids featuring eight-membered rings and helicene units
From the themed collection: 2023 Chemical Science HOT Article Collection
Open Access Edge Article

Substituent effects on paratropicity and diatropicity in π-extended hexapyrrolohexaazacoronene

Substituent effects in antiaromatic homoHPHAC+ and aromatic homoHPHAC3+ were investigated by NMR, crystal structure, redox, absorption, and DFT calculation analyses.

Graphical abstract: Substituent effects on paratropicity and diatropicity in π-extended hexapyrrolohexaazacoronene
From the themed collection: Emerging Frontiers in Aromaticity
Open Access Edge Article

Substituent effects on aromatic interactions in water

Measurements using chemical double mutant cycles show that electron-withdrawing groups lead to remarkable increases in the stability of aromatic interactions, and the magnitude of the effect is much larger in water than in chloroform solution.

Graphical abstract: Substituent effects on aromatic interactions in water
From the themed collection: Emerging Frontiers in Aromaticity
Open Access Edge Article

Rational design of anti-Kasha photoemission from a biazulene core embedded in an antiaromatic/aromatic hybrid

Design of anti-Kasha emitters based on the J-coupling of azulenes and molecular rigidity imposed by antiaromatic/aromatic embedding.

Graphical abstract: Rational design of anti-Kasha photoemission from a biazulene core embedded in an antiaromatic/aromatic hybrid
From the themed collection: Emerging Frontiers in Aromaticity
Open Access Edge Article

From closed-shell edge-extended kekulenes to open-shell carbonylated cycloarene diradicaloid

A series of closed-shell kekulene homologues and an open-shell carbonylated cycloarene derivative were synthesized successfully by controlling the temperature and gas atmosphere of a Bi(OTf)3-catalyzed cyclization reaction.

Graphical abstract: From closed-shell edge-extended kekulenes to open-shell carbonylated cycloarene diradicaloid
From the themed collection: Emerging Frontiers in Aromaticity
Open Access Edge Article

Fully-fused boron-doped olympicenes: modular synthesis, tunable optoelectronic properties, and one-electron reduction

We report a novel family of boraolympicenes with fully-fused boron-doping at their π-skeletons. The resulting boraolympicenyl radical anion featured a resonant stability under inert conditions benefiting from the borataalkene-containing aromatic resonant form.

Graphical abstract: Fully-fused boron-doped olympicenes: modular synthesis, tunable optoelectronic properties, and one-electron reduction
From the themed collection: Emerging Frontiers in Aromaticity
Open Access Edge Article

Saddle-shaped aza-nanographene with multiple odd-membered rings

Saddle-shaped nanographene encompassing a pyrrolopyrrole core possesses an unusual propensity to oxidize (EHOMO = −4.44 eV) while being stable at ambient conditions.

Graphical abstract: Saddle-shaped aza-nanographene with multiple odd-membered rings
From the themed collection: #MyFirstChemSci 2023
Open Access Edge Article

Disentangling global and local ring currents

Aromatic or antiaromatic ring currents – why not both? We use experimental NMR chemical shifts to identify both local and global ring currents in π-conjugated molecules.

Graphical abstract: Disentangling global and local ring currents
From the themed collection: Emerging Frontiers in Aromaticity
Open Access Edge Article

On-surface synthesis of non-benzenoid conjugated polymers by selective atomic rearrangement of ethynylarenes

Here, we report a new on-surface synthetic strategy to precisely introduce five-membered units into conjugated polymers from specifically designed precursor molecules that give rise to low-bandgap fulvalene-bridged bisanthene polymers.

Graphical abstract: On-surface synthesis of non-benzenoid conjugated polymers by selective atomic rearrangement of ethynylarenes
From the themed collection: Emerging Frontiers in Aromaticity
Open Access Edge Article

Heterocyclic Suzuki–Miyaura coupling reaction of metalla-aromatics and mechanistic analysis of site selectivity

We describe unique polyhalogenated heteroarene candidates for site-selective cross-coupling, which shows high catalytic performances in the functionalization of polycyclic metalla-aromatics with excellent photophysical properties.

Graphical abstract: Heterocyclic Suzuki–Miyaura coupling reaction of metalla-aromatics and mechanistic analysis of site selectivity
From the themed collection: Emerging Frontiers in Aromaticity
Open Access Edge Article

Synthesis and characterization of bi(metallacycloprop-1-ene) complexes

Well-defined metallacycloprop-1-ene complexes have only previously been isolated with a metal center bearing one vinyl moiety. We have successfully obtained the first examples of structurally characterized spiro bi(metallacycloprop-1-ene) complexes.

Graphical abstract: Synthesis and characterization of bi(metallacycloprop-1-ene) complexes
From the themed collection: 2023 Chemical Science HOT Article Collection
Open Access Edge Article

Conjugation between 3D and 2D aromaticity: does it really exist? The case of carborane-fused heterocycles

We have demonstrated that carborane fused heterocycles can definitely be considered as non-2D aromatic compounds; therefore, their aromatic character was significantly overestimated in earlier studies.

Graphical abstract: Conjugation between 3D and 2D aromaticity: does it really exist? The case of carborane-fused heterocycles
From the themed collection: Emerging Frontiers in Aromaticity
Open Access Edge Article

Aromatic heterobicycle-fused porphyrins: impact on aromaticity and excited state electron transfer leading to long-lived charge separation

π-Extended porphyrins fused with benzo[4,5]imidazo[2,1-a]isoindole, showing unique electronic and photophysical properties, were newly synthesized. A long-lived charge-separated state was revealed upon coordination of C60 to zinc porphyrin AMIm-2.

Graphical abstract: Aromatic heterobicycle-fused porphyrins: impact on aromaticity and excited state electron transfer leading to long-lived charge separation
From the themed collection: Emerging Frontiers in Aromaticity
Open Access Edge Article

The smallest 4f-metalla-aromatic molecule of cyclo-PrB2 with Pr–B multiple bonds

We report the smallest 4f-metalla-aromatic molecule of PrB2 exhibiting σ and π double aromaticity and multiple Pr–B bond characters.

Graphical abstract: The smallest 4f-metalla-aromatic molecule of cyclo-PrB2− with Pr–B multiple bonds
From the themed collection: Emerging Frontiers in Aromaticity
Open Access Edge Article

From a Möbius-aromatic interlocked Mn2B10H10 wheel to the metal-doped boranaphthalenes M2@B10H8 and M2B5 2D-sheets (M = Mn and Fe): a molecules to materials continuum using DFT studies

The design of (1) Möbius aromatic interlocked boron wheel Mn2B10H10, (2) Hückel aromatic boron analogs of naphthalene (M2@B10H8; M = Mn and Fe), and (3) metal boride monolayers (FeB5 and Fe2B5), creating a molecules to materials continuum.

Graphical abstract: From a Möbius-aromatic interlocked Mn2B10H10 wheel to the metal-doped boranaphthalenes M2@B10H8 and M2B5 2D-sheets (M = Mn and Fe): a molecules to materials continuum using DFT studies
From the themed collection: Emerging Frontiers in Aromaticity
Open Access Edge Article

An unexpected all-metal aromatic tetranuclear silver cluster in human copper chaperone Atox1

Metal clusters, such as iron–sulfur clusters, play key roles in sustaining life and are intimately involved in the functions of metalloproteins.

Graphical abstract: An unexpected all-metal aromatic tetranuclear silver cluster in human copper chaperone Atox1
From the themed collection: Emerging Frontiers in Aromaticity
Open Access Edge Article

Mining anion–aromatic interactions in the Protein Data Bank

The comprehensive analysis of non-redundant PDB macromolecular structures investigating anion distributions around all aromatic molecules in available biosystems is presented.

Graphical abstract: Mining anion–aromatic interactions in the Protein Data Bank
From the themed collection: Emerging Frontiers in Aromaticity
Open Access Edge Article

Enhanced N-directed electrophilic C–H borylation generates BN–[5]- and [6]helicenes with improved photophysical properties

An enhanced N-directed electrophilic C–H borylation methodology has been developed that provides access to azaborine containing helicenes.

Graphical abstract: Enhanced N-directed electrophilic C–H borylation generates BN–[5]- and [6]helicenes with improved photophysical properties
From the themed collection: Emerging Frontiers in Aromaticity
Open Access Edge Article

Polariton ring currents and circular dichroism of Mg-porphyrin in a chiral cavity

Placing aromatic molecules in a chiral optical cavity can break time-reversal symmetry and generate polariton ring currents with a linearly polarized pump. Such currents can be probed by circular dichroism, with one order of magnitude enhancement.

Graphical abstract: Polariton ring currents and circular dichroism of Mg-porphyrin in a chiral cavity
From the themed collection: Emerging Frontiers in Aromaticity
Open Access Edge Article

Visualizing electron delocalization in contorted polycyclic aromatic hydrocarbons

Electron delocalization in contorted polycyclic aromatic hydrocarbon (PAH) molecules was examined through 3D isotropic magnetic shielding (IMS) contour maps built around the molecules using pseudo-van der Waals surfaces.

Graphical abstract: Visualizing electron delocalization in contorted polycyclic aromatic hydrocarbons
From the themed collection: Emerging Frontiers in Aromaticity
Open Access Edge Article

β-Trioxopyrrocorphins: pyrrocorphins of graded aromaticity

The four possible pyrrocorphin isomers were prepared. Remarkably, they show regiochemically dependent aromaticity attributed to the presence of a 16-membered, 18 π-electron aromatic ring-current.

Graphical abstract: β-Trioxopyrrocorphins: pyrrocorphins of graded aromaticity
From the themed collection: Emerging Frontiers in Aromaticity
Open Access Edge Article

Enantiopure nanohoops through racemic resolution of diketo[n]CPPs by chiral derivatization as precursors to DBP[n]CPPs

Racemic resolution of diketone-embedded cycloparaphenylenes by derivatization with a chiral auxiliary provides scalable access to enantiopure hoops with chiroptical properties.

Graphical abstract: Enantiopure nanohoops through racemic resolution of diketo[n]CPPs by chiral derivatization as precursors to DBP[n]CPPs
From the themed collection: Emerging Frontiers in Aromaticity
Open Access Edge Article

Stretching [8]cycloparaphenylene with encapsulated potassium cations: structural and theoretical insights into core perturbation upon four-fold reduction and complexation

Structural and theoretical analysis of a highly-charged [8]cycloparaphenylene reveals drastic elliptic distortion and unique metal encapsulation of the macrocyclic host upon reduction.

Graphical abstract: Stretching [8]cycloparaphenylene with encapsulated potassium cations: structural and theoretical insights into core perturbation upon four-fold reduction and complexation
From the themed collection: Emerging Frontiers in Aromaticity
Open Access Edge Article

Direct amidation of metallaaromatics: access to N-functionalized osmapentalynes via a 1,5-bromoamidated intermediate

The direct C–H amidation of metallapentalyne has been achieved under mild conditions in which key 1,5-bromoamidated intermediates was determined.

Graphical abstract: Direct amidation of metallaaromatics: access to N-functionalized osmapentalynes via a 1,5-bromoamidated intermediate
From the themed collection: Emerging Frontiers in Aromaticity
Open Access Edge Article

Asymmetric systematic synthesis, structures, and (chir)optical properties of a series of dihetero[8]helicenes

A series of dihetero[8]helicenes have been synthesized in a stereoselective manner through an organosulfur-based synthetic strategy, which has enabled clarifying the effect of the endocyclic atoms on physical properties.

Graphical abstract: Asymmetric systematic synthesis, structures, and (chir)optical properties of a series of dihetero[8]helicenes
From the themed collection: Emerging Frontiers in Aromaticity
Open Access Edge Article

Synthesis, crystal structure and charge transport characteristics of stable peri-tetracene analogues

Highly stable peri-tetracene analogues with a high degree of singlet biradical character were synthesized in a very simple route, and their crystal structures and semiconducting properties were investigated.

Graphical abstract: Synthesis, crystal structure and charge transport characteristics of stable peri-tetracene analogues
From the themed collection: Emerging Frontiers in Aromaticity
Open Access Edge Article

“Bottled” spiro-doubly aromatic trinuclear [Pd2Ru]+ complexes

Synthesis of a triangular [Pd2Ru]+ complex with delocalized metal–metal bonding between non-adjacent elements of the periodic table, double aromaticity and overlap of d-AOs with different angular momentum.

Graphical abstract: “Bottled” spiro-doubly aromatic trinuclear [Pd2Ru]+ complexes
From the themed collection: Emerging Frontiers in Aromaticity
Open Access Commentary

A focus on aromaticity: fuzzier than ever before?

The field of aromaticity has grown extensively in recent decades, and new or unusual forms of aromaticity have been explored. But what exactly is aromaticity? It has always been a fuzzy and disputable concept, yet, is it now fuzzier than ever before?

Graphical abstract: A focus on aromaticity: fuzzier than ever before?
From the themed collection: Emerging Frontiers in Aromaticity
31 items

About this collection

Although benzene was discovered almost two centuries ago, the attraction of aromaticity continues to intrigue chemists worldwide. This themed collection is introduced by guest editors Miquel Solà (Universitat de Girona), Israel Fernández (Universidad Complutense de Madrid), and Gabriel Merino (Cinvestav Mérida), who highlight the panorama of aromaticity research in modern chemistry. Their selection highlights the most recent methodological developments and unique aspects of aromaticity, such as metalla-aromaticity, macrocyclic aromaticity, 3D-aromaticity, Möbius aromaticity, and the aromaticity of polycyclic conjugated hydrocarbons and nanographenes.

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