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Themed collection Aromaticity

45 articles
Editorial

Aromaticity: a web themed issue

Showcasing a collection of cutting edge contributions by international leaders in the field of aromaticity.

Graphical abstract: Aromaticity: a web themed issue
From the themed collection: Aromaticity
Feature Article

Molecular early main group metal hydrides: synthetic challenge, structures and applications

Ligand-stabilized early main group metal hydride clusters.

Graphical abstract: Molecular early main group metal hydrides: synthetic challenge, structures and applications
From the themed collection: Aromaticity
Feature Article

Synthesis of π-extended porphyrins via intramolecular oxidative coupling

Fusion of porphyrins with other aromatic units at the meso- and β-positions results in very strong bathochromic shifts of absorption.

Graphical abstract: Synthesis of π-extended porphyrins via intramolecular oxidative coupling
From the themed collection: Aromaticity
Feature Article

Coarctate cyclization reactions: a primer

Coarctate reactivity, typical of molecules in the conjugated ‘ene–ene–yne’ manifold, can be harnessed to generate unique classes of heterocyclic compounds.

Graphical abstract: Coarctate cyclization reactions: a primer
From the themed collection: Aromaticity
Feature Article

The chemistry of four-membered aromatics

This feature article overviews and summarizes aromaticity of the four-membered ring systems to discuss expanding chemistry of the aromaticity concept.

Graphical abstract: The chemistry of four-membered aromatics
From the themed collection: Aromaticity
Feature Article

Oxidative transformation of aryls using molybdenum pentachloride

Aryl–aryl bonds can effectively be formed using molybdenum pentachloride to obtain uncommon geometries tolerating a broad scope of functional groups.

Graphical abstract: Oxidative transformation of aryls using molybdenum pentachloride
From the themed collection: Aromaticity
Communication

Tunable star-shaped triphenylamine fluorophores for fluorescence quenching detection and identification of nitro-aromatic explosives

Triphenylamine-based fluorophores containing pyrene or corannulene show variable fluorescence quenching sensitivity toward nitro explosives.

Graphical abstract: Tunable star-shaped triphenylamine fluorophores for fluorescence quenching detection and identification of nitro-aromatic explosives
From the themed collection: Aromaticity
Communication

The 4,5,6-triphospha[3]radialene dianion: a phosphorus analogue of the deltate dianion. A NICS(0)πzz examination of their aromaticity

Reduction of a 4,5,6-triphospha[3]radialene gave the corresponding isolable dianionic species.

Graphical abstract: The 4,5,6-triphospha[3]radialene dianion: a phosphorus analogue of the deltate dianion. A NICS(0)πzz examination of their aromaticity
From the themed collection: Aromaticity
Communication

Unusual para-substituent effects on the intramolecular hydrogen-bond in hydrazone-based switches

A “V”-shaped Hammett plot shows that resonance-assisted hydrogen bonding does not dictate the strength of the intramolecular hydrogen bond in the E isomers of hydrazone-based switches.

Graphical abstract: Unusual para-substituent effects on the intramolecular hydrogen-bond in hydrazone-based switches
From the themed collection: Aromaticity
Communication

On the aromatic stabilization of benzenoid hydrocarbons

We present a general scheme for estimation of aromatic stabilization energies of benzenoid hydrocarbons based on selected topological features.

Graphical abstract: On the aromatic stabilization of benzenoid hydrocarbons
From the themed collection: Aromaticity
Communication

Molecular nesting in co-crystals of tetrabenzoquadrannulene and C60: application of the sphere in a cone model

The interaction between C60 and tetrabenzoquadrannulene, observed by X-ray diffraction analysis, is understood using DFT-D calculations and a sphere-in-cone model.

Graphical abstract: Molecular nesting in co-crystals of tetrabenzoquadrannulene and C60: application of the sphere in a cone model
From the themed collection: Aromaticity
Communication

Highly fluorescent benzofuran derivatives of the GFP chromophore

Intramolecular cyclization of alkynyl-substituted derivatives of the Green Fluorescent Protein chromophore into benzofuran derivatives presents a simple way of enhancing its fluorescence.

Graphical abstract: Highly fluorescent benzofuran derivatives of the GFP chromophore
From the themed collection: Aromaticity
Communication

π-Depletion as a criterion to predict π-stacking ability

The LOLIPOP criterion identifies π-depleted polyaromatic molecules, which exhibit enhanced π-stacking ability.

Graphical abstract: π-Depletion as a criterion to predict π-stacking ability
From the themed collection: Aromaticity
Communication

Synthesis of 3,7-diiodo-2,6-di(thiophen-2-yl)benzo[1,2-b:4,5-b′]difurans: functional building blocks for the design of new conjugated polymers

Iodine-catalyzed cyclization is used to prepare benzodifurans that can be further functionalized to alter their properties.

Graphical abstract: Synthesis of 3,7-diiodo-2,6-di(thiophen-2-yl)benzo[1,2-b:4,5-b′]difurans: functional building blocks for the design of new conjugated polymers
From the themed collection: Aromaticity
Communication

Merging tribenzotriquinacene with hexa-peri-hexabenzocoronene: a cycloheptatriene unit generated by Scholl reaction

A bay-bridging Scholl reaction converts the pentaphenylphenyl-substituted tribenzotriquinacene 1 into the curved hexa-peri-hexabenzocoronene-TBTQ derivative 2 bearing a newly formed cycloheptatriene ring.

Graphical abstract: Merging tribenzotriquinacene with hexa-peri-hexabenzocoronene: a cycloheptatriene unit generated by Scholl reaction
From the themed collection: Aromaticity
Communication

Highly π electron-rich macro-aromatics: bis(p-aminophenyl)-carbo-benzenes and their DBA acyclic references

A series of quadrupolar bis(p-aminophenyl)-carbo-benzenes (bottom) is compared to the acyclic carbo-butadiene (top) reference series.

Graphical abstract: Highly π electron-rich macro-aromatics: bis(p-aminophenyl)-carbo-benzenes and their DBA acyclic references
From the themed collection: Aromaticity
Communication

A small molecule two-photon probe for hydrogen sulfide in live tissues

We report a two-photon probe (FS1) which shows a 21-fold two-photon excited fluorescence enhancement in response to H2S and can selectively detect H2S in a rat hippocampal slice at a depth of 90–190 μm by using two-photon microscopy.

Graphical abstract: A small molecule two-photon probe for hydrogen sulfide in live tissues
From the themed collection: Aromaticity
Communication

Is cyclobutadiene really highly destabilized by antiaromaticity?

The high energy of cyclobutadiene (CBD) is not due primarily to “anti-aromaticity,” but rather to angle strain and Pauli repulsion between close-by parallel CC σ and π bonds.

Graphical abstract: Is cyclobutadiene really highly destabilized by antiaromaticity?
From the themed collection: Aromaticity
Communication

Dibenz[a,c]anthracene derivatives exhibiting columnar mesophases over broad temperature ranges

The mesomorphic properties of a series of novel dibenz[a,c]anthracenes display remarkable sensitivity to substituents and in some cases these compounds exhibit mesophases over broad temperature ranges.

Graphical abstract: Dibenz[a,c]anthracene derivatives exhibiting columnar mesophases over broad temperature ranges
From the themed collection: Aromaticity
Communication

Core-extended rylene dyes via thiophene annulation

Annulation of thiophenes directly into the bay regions of rylene dyes leads to core-extended rylene tetracarboxylic diimides with interesting electro-optical properties.

Graphical abstract: Core-extended rylene dyes via thiophene annulation
From the themed collection: Aromaticity
Communication

Synthesis and charge transport studies of stable, soluble hexacenes

We report the synthesis and charge transport characterization of soluble hexacenes, including ambipolar behavior from an octafluoro hexacene.

Graphical abstract: Synthesis and charge transport studies of stable, soluble hexacenes
From the themed collection: Aromaticity
Communication

An experimental estimate of the relative aromaticity of the cyclooctatetraene dianion by fusion to dimethyldihydropyrene

The relative aromaticity of COT2− is experimentally as large as benzene, and larger than that of the cyclopentadienide anion.

Graphical abstract: An experimental estimate of the relative aromaticity of the cyclooctatetraene dianion by fusion to dimethyldihydropyrene
From the themed collection: Aromaticity
Communication

Palladium-catalysed heteroannulation of [60]fullerene with N-benzyl sulfonamides and subsequent functionalisation

The palladium-catalysed heteroannulation of [60]fullerene with N-benzyl sulfonamides via C–H activation affords [60]fullerene-fused tetrahydroisoquinolines, which can be further functionalised.

Graphical abstract: Palladium-catalysed heteroannulation of [60]fullerene with N-benzyl sulfonamides and subsequent functionalisation
From the themed collection: Aromaticity
Communication

Synthesis of electron-poor hexa-peri-hexabenzocoronenes

A series of hexa-peri-hexabenzocoronenes with electron withdrawing groups were obtained via oxidative cyclodehydrogenation with an oxidant and a strong acid.

Graphical abstract: Synthesis of electron-poor hexa-peri-hexabenzocoronenes
From the themed collection: Aromaticity
Communication

Diels–Alder cycloaddition of acetylene gas to a polycyclic aromatic hydrocarbon bay region

Acetylene might suffice as a dienophile for growing uniform carbon nanotubes from small hydrocarbon templates by the Diels–Alder cycloaddition/rearomatization strategy.

Graphical abstract: Diels–Alder cycloaddition of acetylene gas to a polycyclic aromatic hydrocarbon bay region
From the themed collection: Aromaticity
Communication

Chemically modified graphene oxides as a hole transport layer in organic solar cells

O2 plasma treated GO with a work function of 5.2 eV as a high performance hole transport layer in organic solar cells.

Graphical abstract: Chemically modified graphene oxides as a hole transport layer in organic solar cells
From the themed collection: Aromaticity
Communication

Relationship of charge to antiaromaticity in bis-fluorenyl dications and fluorenyl monocations: experimental support for theoretical calculations

Antiaromaticity of fluorenyl cations can be moderated through the use of substituents to change the amount of charge density.

Graphical abstract: Relationship of charge to antiaromaticity in bis-fluorenyl dications and fluorenyl monocations: experimental support for theoretical calculations
From the themed collection: Aromaticity
Communication

Synthesis and structure of 1,4,5,8-tetraethynylnaphthalene derivatives

1,4,5,8-Tetraethynylnaphthalene derivatives were synthesized for the first time. X-ray crystallographic structure analysis of the tetrakis(phenylethynyl) substituted derivative revealed three different modes of distortion to reduce steric repulsion.

Graphical abstract: Synthesis and structure of 1,4,5,8-tetraethynylnaphthalene derivatives
From the themed collection: Aromaticity
Communication

Tetrakis(4-tert-butylphenyl) substituted and fused quinoidal porphyrins

Tetrakis(4-tert-butylphenyl) substituted and fused quinoidal porphyrins are prepared for the first time, which show unique geometry, electronic structure and optical properties.

Graphical abstract: Tetrakis(4-tert-butylphenyl) substituted and fused quinoidal porphyrins
From the themed collection: Aromaticity
Communication

Concise, aromatization-based approach to an elaborate C2-symmetric pyrenophane

A multicomponent reaction and a double McMurry/valence isomerization/dehydrogenation reaction conspire to create the entire pyrene system in a highly decorated [12](1,6)pyrenophane.

Graphical abstract: Concise, aromatization-based approach to an elaborate C2-symmetric pyrenophane
From the themed collection: Aromaticity
Communication

Straightforward synthesis of phenanthrenes from styrenes and arenes

A semi-one-pot synthesis of phenanthrenes from styrenes and arenes has been developed which provides an effective and practical protocol.

Graphical abstract: Straightforward synthesis of phenanthrenes from styrenes and arenes
From the themed collection: Aromaticity
Communication

A rigid donor–acceptor daisy chain dimer

A functionalised cyclobis(paraquat-p-phenylene) attached by a rigid linker to a tetrathiafulvalene unit, which is incapable of self-complexation, forms preferentially a [c2]daisy chain which undergoes rapid disassociation and reassociation on the 1H NMR time-scale above room temperature.

Graphical abstract: A rigid donor–acceptor daisy chain dimer
From the themed collection: Aromaticity
Communication

α-Oligofurans show a sizeable extent of π-conjugation as probed by Raman spectroscopy

Raman spectroscopic analysis of long α-oligofurans and polyfuran shows that extension of the π-conjugation in polyfuran spreads over 14–15 furan units.

Graphical abstract: α-Oligofurans show a sizeable extent of π-conjugation as probed by Raman spectroscopy
From the themed collection: Aromaticity
Communication

1,3,5-Triaryl 2-pyridylidene: base-promoted generation and complexation

We herein report a base-promoted generation and complexation of sterically hindered 1,3,5-triaryl 2-pyridylidene from the corresponding pyridinium salt.

Graphical abstract: 1,3,5-Triaryl 2-pyridylidene: base-promoted generation and complexation
From the themed collection: Aromaticity
Communication

Meta-B-entacenes: new polycyclic aromatics incorporating two fused borepin rings

New, curved boron-containing acenes have been synthesized, demonstrating cathodic electrochemistry, strong photoluminescence, and facile cross-coupling to give π-extended scaffolds.

Graphical abstract: Meta-B-entacenes: new polycyclic aromatics incorporating two fused borepin rings
From the themed collection: Aromaticity
Communication

A C84 selective porphyrin macrocycle with an adaptable cavity constructed through alkyne metathesis

A bisporphyrin macrocycle with an adaptable cavity showing a high binding selectivity for C84 over lower fullerenes (C60 and C70).

Graphical abstract: A C84 selective porphyrin macrocycle with an adaptable cavity constructed through alkyne metathesis
From the themed collection: Aromaticity
Communication

Angular-shaped naphthodifurans, naphtho[1,2-b;5,6-b′]- and naphtho[2,1-b;6,5-b′]-difuran: are they isoelectronic with chrysene?

The chalcogen atoms make a marked difference in the ground state electronic structure.

Graphical abstract: Angular-shaped naphthodifurans, naphtho[1,2-b;5,6-b′]- and naphtho[2,1-b;6,5-b′]-difuran: are they isoelectronic with chrysene?
From the themed collection: Aromaticity
Communication

Aromaticity and π-bond covalency: prominent intermolecular covalent bonding interaction of a Kekulé hydrocarbon with very significant singlet biradical character

A prominent covalent bonding interaction between molecules is experimentally elucidated in a one-dimensional stack of an anthracene-linked bisphenalenyl Kekulé molecule by using polarized reflection spectroscopy.

Graphical abstract: Aromaticity and π-bond covalency: prominent intermolecular covalent bonding interaction of a Kekulé hydrocarbon with very significant singlet biradical character
From the themed collection: Aromaticity
Communication

Diazaheterocycle analogues of tetracene: synthesis and properties of a naphtho-fused cinnoline and a naphtho-fused isoindazole

Two fluorescent, diaza-analogues of tetracene can be prepared independently from a common triazene-ene-yne precursor via either a pericyclic or coarctate ring-forming reaction.

Graphical abstract: Diazaheterocycle analogues of tetracene: synthesis and properties of a naphtho-fused cinnoline and a naphtho-fused isoindazole
From the themed collection: Aromaticity
Communication

Rearrangement from the heteroantiaromatic borole to the heteroaromatic azaborine motif

Treatment of 9-chloro-9-borafluorene with N,O-(bistrimethylsilyl)hydroxylamine produces an azaborine derivative.

Graphical abstract: Rearrangement from the heteroantiaromatic borole to the heteroaromatic azaborine motif
From the themed collection: Aromaticity
Communication

Deterioration of bulk heterojunction organic photovoltaic devices by a minute amount of oxidized fullerene

Addition of SIMEF-O2 to the active layer of organic photovoltaic devices decreased their performance.

Graphical abstract: Deterioration of bulk heterojunction organic photovoltaic devices by a minute amount of oxidized fullerene
From the themed collection: Aromaticity
Communication

Reversible dispersion and releasing of single-walled carbon nanotubes by a stimuli-responsive TTFV-phenylacetylene polymer

A TTFV-phenylacetylene folding polymer exhibits the property of reversibly dispersing and releasing single-walled carbon nanotubes in organic solvents under the control of redox or pH stimuli.

Graphical abstract: Reversible dispersion and releasing of single-walled carbon nanotubes by a stimuli-responsive TTFV-phenylacetylene polymer
From the themed collection: Aromaticity
Communication

Triply ferrocene-bridged boroxine cyclophane

Solvothermal dehydration of 1,1′-ferrocenediboronic acid produces single crystals of a triply ferrocene-bridged boroxine cyclophane.

Graphical abstract: Triply ferrocene-bridged boroxine cyclophane
From the themed collection: Aromaticity
Communication

The high yielding synthesis of pillar[5]arenes under Friedel–Crafts conditions explained by dynamic covalent bond formation

Systematic investigations on Friedel–Crafts reactions from building blocks A, B and C have been carried out to demonstrate that the formation of pillar[5]arenes occurs under thermodynamic control.

Graphical abstract: The high yielding synthesis of pillar[5]arenes under Friedel–Crafts conditions explained by dynamic covalent bond formation
From the themed collection: Aromaticity
Communication

Synthesis of a green [60]fullerene derivative through cage-opening reactions

Open-cage derivative C60(O)4(OH)2(NC6H4tBu)2 reacts with ICl to form a Baeyer–Villiger type product, which yields an intense green product upon treatment with HI.

Graphical abstract: Synthesis of a green [60]fullerene derivative through cage-opening reactions
From the themed collection: Aromaticity
45 articles

About this collection

This web-based themed issue highlights recent achievements in chemistry related to aromaticity. You will find research ranging from new fundamental knowledge about aromaticity and theoretically interesting new arene structures to novel applications of aromatics and heteroaromatics which take advantage of their unique optical and electronic attributes and, in general, on those processes in which the gain or loss of aromaticity play an important role.

The guest editors for this issue are Nazario Martín (University Complutense of Madrid), Michael Haley (University of Oregon) and Rik Tykwinski (University of Erlangen-Nuremberg).

Articles in this web themed issue will be added below as soon as possible after they are published. Please return to this page frequently to see the collection grow.

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