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Themed collection Novel π-electron molecular scaffolds

38 articles
Editorial

Novel π-electron molecular scaffolds: a themed issue

Novel π-electron molecular scaffolds with exciting properties will bring new discussions and excitement to the chemical community.

Graphical abstract: Novel π-electron molecular scaffolds: a themed issue
From the themed collection: Novel π-electron molecular scaffolds
Review Article

Nanocalipers as novel molecular scaffolds for carbon nanotubes

Nanocalipers were synthesized by connecting directly the five aromatic moieties including two receptors, two corners and a core, and found to discriminate the diameter, metallicity and handedness of carbon nanotubes through selective complexation.

Graphical abstract: Nanocalipers as novel molecular scaffolds for carbon nanotubes
From the themed collection: Novel π-electron molecular scaffolds
Review Article

Methodology and applications of the hexadehydro-Diels–Alder (HDDA) reaction

Hexadehydro-Diels–Alder (HDDA) reactions between alkynes and 1,3-diynes readily generate highly reactive and synthetically useful arynes.

Graphical abstract: Methodology and applications of the hexadehydro-Diels–Alder (HDDA) reaction
From the themed collection: Novel π-electron molecular scaffolds
Research Article

Pentadecaphenylenes: synthesis, self-assembly and complexation with fullerene C60

Macrocyclic pentadecaphenylene incorporates fullerene C60 in its cavity to afford fibrous 2 : 1 and 1 : 1 sandwich complexes.

Graphical abstract: Pentadecaphenylenes: synthesis, self-assembly and complexation with fullerene C60
From the themed collection: Novel π-electron molecular scaffolds
Research Article

6,6′,11,11′-Tetra((triisopropylsilyl)ethynyl)-anti-[2.2](1,4)tetracenophane: a covalently coupled tetracene dimer and its structural, electrochemical, and photophysical characterization

[2.2]-Acenophanes are a class of compounds with two acene units interconnected by two ethano bridges.

Graphical abstract: 6,6′,11,11′-Tetra((triisopropylsilyl)ethynyl)-anti-[2.2](1,4)tetracenophane: a covalently coupled tetracene dimer and its structural, electrochemical, and photophysical characterization
From the themed collection: Novel π-electron molecular scaffolds
Research Article

Pyrene-fused bisphenazinothiadiazoles with red to NIR electroluminescence

Deep red and NIR electroluminescence from pyrene-fused bisphenazinothiadiazoles.

Graphical abstract: Pyrene-fused bisphenazinothiadiazoles with red to NIR electroluminescence
From the themed collection: Novel π-electron molecular scaffolds
Research Article

Synthesis of 2,3-diaza-anthraquinones via the bidentate Lewis acid catalysed inverse electron-demand Diels–Alder (IEDDA) reaction

A new synthesis of aza-anthraquinones and substituted anthraquinones via bidentate Lewis acid catalysis has been developed.

Graphical abstract: Synthesis of 2,3-diaza-anthraquinones via the bidentate Lewis acid catalysed inverse electron-demand Diels–Alder (IEDDA) reaction
From the themed collection: Novel π-electron molecular scaffolds
Research Article

Planar versus triptycenylene end-capped aroyleneimidazoles as electron acceptors in organic photovoltaics

The effect of triptycenylene end-groups on the optoelectronic properties of aroyleneimidazoles and their performance as acceptors in bulk heterojunction photovoltaic devices are described.

Graphical abstract: Planar versus triptycenylene end-capped aroyleneimidazoles as electron acceptors in organic photovoltaics
From the themed collection: Novel π-electron molecular scaffolds
Research Article

Polycyclic heteroaromatic hydrocarbons containing a benzoisoindole core

By the combination of 9a-azaphenalene and a perpendicularly oriented acene, we have synthesized three derivatives of a series of novel, fully-conjugated nitrogen-containing polycyclic aromatic hydrocarbons (PAHs).

Graphical abstract: Polycyclic heteroaromatic hydrocarbons containing a benzoisoindole core
From the themed collection: Novel π-electron molecular scaffolds
Research Article

Radical cation and dication of a 4H-dithieno[2,3-b:3′,2′-e][1,4]-thiazine

4H-Dithieno[2,3-b:3’,2’-e][1,4]-thiazine (DTT), and its radical cation and dication were synthesized, characterized (EPR spectroscopy and spectroelectrochemistry) and interpreted (DFT and TD DFT calculations).

Graphical abstract: Radical cation and dication of a 4H-dithieno[2,3-b:3′,2′-e][1,4]-thiazine
From the themed collection: Novel π-electron molecular scaffolds
Research Article

Unexpected formation of [5]helicenes from hexaarylbenzenes containing pyrrole moieties

Surprisingly helical: a pyrrolic [5]helicene embedded into a six-membered ring framework is preferred over a heterocyclic pendant of hexabenzocoronene.

Graphical abstract: Unexpected formation of [5]helicenes from hexaarylbenzenes containing pyrrole moieties
From the themed collection: Novel π-electron molecular scaffolds
Research Article

Synthesis of largely π-extended naphthalenediimides via C–H activation towards highly soluble and narrow band-gap organic optoelectronic materials

Largely π-extended naphthalenediimides were synthesized by using efficient palladium catalyzed C–H/C–H homocouplings, with the yields of up to 94%.

Graphical abstract: Synthesis of largely π-extended naphthalenediimides via C–H activation towards highly soluble and narrow band-gap organic optoelectronic materials
From the themed collection: Novel π-electron molecular scaffolds
Research Article

Anthroxyl-based biradical: toward the construction of highly stable multi-spin systems

A new two-spin system having two anthroxyl radicals was found to be stable even after exposing it to refluxing ethanol.

Graphical abstract: Anthroxyl-based biradical: toward the construction of highly stable multi-spin systems
From the themed collection: Novel π-electron molecular scaffolds
Research Article

Functionalization of pentacene-5,7,12,14-tetraone with geminal enediyne and 1,3-dithiole groups

Pentacene-5,7,12,14-tetraone was subjected to selective olefination and cross-coupling reactions to yield a new class of pentacene-based π-conjugated systems with intriguing structural, electronic, and redox properties.

Graphical abstract: Functionalization of pentacene-5,7,12,14-tetraone with geminal enediyne and 1,3-dithiole groups
From the themed collection: Novel π-electron molecular scaffolds
Research Article

Electronic and steric effects on the three-fold Scholl-type cycloheptatriene ring formation around a tribenzotriquinacene core

Single and triple bay-bridging Scholl-type cyclizations of several 1,4,8-triaryl-substituted tribenzotriquinacenes are subject to pronounced electronic and steric substituent effects.

Graphical abstract: Electronic and steric effects on the three-fold Scholl-type cycloheptatriene ring formation around a tribenzotriquinacene core
From the themed collection: Novel π-electron molecular scaffolds
Research Article

Twisted terrylene dyes: synthesis and application in organic solar cells

Two twisted terrylene diimides as non-fullerene acceptors for solar cells have been designed with a resulting power conversion efficiency of 3.64%.

Graphical abstract: Twisted terrylene dyes: synthesis and application in organic solar cells
From the themed collection: Novel π-electron molecular scaffolds
Research Article

The effect of a highly twisted C[double bond, length as m-dash]C double bond on the electronic structures of 9,9′-bifluorenylidene derivatives in the ground and excited states

A highly twisted C[double bond, length as m-dash]C double bond elicits changes in the physicochemical properties of π-systems.

Graphical abstract: The effect of a highly twisted C [[double bond, length as m-dash]] C double bond on the electronic structures of 9,9′-bifluorenylidene derivatives in the ground and excited states
From the themed collection: Novel π-electron molecular scaffolds
Research Article

Tuning liquid crystalline phase behaviour in columnar crown ethers by sulfur substituents

Sulfur-containing side chains in the periphery of o-terphenyl or triphenylene units of crown ethers induce room-temperature columnar mesophases.

Graphical abstract: Tuning liquid crystalline phase behaviour in columnar crown ethers by sulfur substituents
From the themed collection: Novel π-electron molecular scaffolds
Research Article

Poly[2(6)-aminoazulene]: synthesis, photophysical properties, and proton conductivity

Dimeric aminoazulene and poly[2(6)-aminoazulene] are synthesized by Buchwald–Hartwig coupling of the corresponding monomeric carbamatoaminozulenes followed by hydrolysis.

Graphical abstract: Poly[2(6)-aminoazulene]: synthesis, photophysical properties, and proton conductivity
From the themed collection: Novel π-electron molecular scaffolds
Research Article

A theoretical study on quasi-one-dimensional open-shell singlet ladder oligomers: multi-radical nature, aromaticity and second hyperpolarizability

Quasi-one-dimensional open-shell singlet ladder oligomers composed of indenofluorene-like units show strong correlation between multiradical nature, aromaticity and second hyperpolarizability.

Graphical abstract: A theoretical study on quasi-one-dimensional open-shell singlet ladder oligomers: multi-radical nature, aromaticity and second hyperpolarizability
From the themed collection: Novel π-electron molecular scaffolds
Research Article

meso-to-meso PtII-bridged NiII-porphyrin dimers

The synthesis and characterization of a series of meso-to-meso PtII-bridged NiII-porphyrin dimers are described.

Graphical abstract: meso-to-meso PtII-bridged NiII-porphyrin dimers
From the themed collection: Novel π-electron molecular scaffolds
Research Article

A new fluorophore displaying remarkable solvatofluorochromism and solid-state light emission, and serving as a turn-on fluorescent sensor for cyanide ions

A new fluorophore displays remarkable solvatofluorochromism, a CIEE effect, and an intense blue-green fluorescence in the presence of cyanide ions.

Graphical abstract: A new fluorophore displaying remarkable solvatofluorochromism and solid-state light emission, and serving as a turn-on fluorescent sensor for cyanide ions
From the themed collection: Novel π-electron molecular scaffolds
Research Article

Synthesis of homoazafullerene [C59N(CH2)]R and azahomoazafullerene [C59N(NH)]R

The selective insertion of a CH2 or NH group is achieved through the PCl5 induced reaction of a CH2OH or NHOH group, respectively.

Graphical abstract: Synthesis of homoazafullerene [C59N(CH2)]R and azahomoazafullerene [C59N(NH)]R
From the themed collection: Novel π-electron molecular scaffolds
Research Article

Synthesis and properties of electron accepting star-shaped phosphaviologen oligomers

A straightforward synthetic route toward redox-active tri- and tetrastar phosphaviologen oligomers that show the intriguing ability of storing up to 8 electrons is reported.

Graphical abstract: Synthesis and properties of electron accepting star-shaped phosphaviologen oligomers
From the themed collection: Novel π-electron molecular scaffolds
Research Article

The influence of the central acceptor unit on the optoelectronic properties and photovoltaic performance of A–D–A–D–A-type co-oligomers

A series of A–D–A–D–A co-oligomers was developed and implemented as donor materials in solution-processable organic solar cells showing the dependence of molecular structures on the power conversion efficiency upon solvent vapor annealing.

Graphical abstract: The influence of the central acceptor unit on the optoelectronic properties and photovoltaic performance of A–D–A–D–A-type co-oligomers
From the themed collection: Novel π-electron molecular scaffolds
Research Article

Synthesis, solvent-dependent emission and two-photon absorption of a triangular –[D–π–A]3– macrocycle

A large π–conjugated macrocycle featuring a –[D–π–A]3– backbone is synthesized, exhibiting strongly solvent-dependent fluorescence and evident two-photon absorption ability.

Graphical abstract: Synthesis, solvent-dependent emission and two-photon absorption of a triangular –[D–π–A]3– macrocycle
From the themed collection: Novel π-electron molecular scaffolds
Open Access Research Article

The impact of interplay between electronic and steric effects on the synthesis and the linear and non-linear optical properties of diketopyrrolopyrrole bearing benzofuran moieties

Benzofuran has been proven to be the versatile substituent for tuning the optics of diketopyrrolopyrroles.

Graphical abstract: The impact of interplay between electronic and steric effects on the synthesis and the linear and non-linear optical properties of diketopyrrolopyrrole bearing benzofuran moieties
From the themed collection: Novel π-electron molecular scaffolds
Research Article

Fast construction of dianthraceno[a,e]pentalenes for OPV applications

A new method based on a palladium-catalyzed tandem reaction for the fast construction of a dianthraceno[a,e]pentalene (DAP) framework is developed, which gave a series of dianthraceno[a,e]pentalenes with good functional group tolerance, and it should be highlighted that five C–C bonds were formed in one reaction.

Graphical abstract: Fast construction of dianthraceno[a,e]pentalenes for OPV applications
From the themed collection: Novel π-electron molecular scaffolds
Research Article

5-Azadibenzo[a,g]corannulene

The first azacorannulene with a nitrogen on the rim, has been synthesized in seven steps from 4-bromoisoquinoline.

Graphical abstract: 5-Azadibenzo[a,g]corannulene
From the themed collection: Novel π-electron molecular scaffolds
Research Article

Selective thionation of naphtho[2,3-b]thiophene diimide: tuning of the optoelectronic properties and packing structure

Naphtho[2,3-b]thiophene diimide was selectively thionated to afford the corresponding dicarboxy-dithiocarboxy diimide with a low-lying LUMO of −4.2 eV.

Graphical abstract: Selective thionation of naphtho[2,3-b]thiophene diimide: tuning of the optoelectronic properties and packing structure
From the themed collection: Novel π-electron molecular scaffolds
Research Article

From tetrabenzoheptafulvalene to sp2 carbon nano-rings

A new kind of sp2 carbon nano-rings containing a heptagon and an octagon was synthesized by taking advantage of the “C” shape of syn-tetrabenzoheptafulvalene.

Graphical abstract: From tetrabenzoheptafulvalene to sp2 carbon nano-rings
From the themed collection: Novel π-electron molecular scaffolds
Research Article

Quasi-planar diazadithio and diazodiseleno[8]circulenes: synthesis, structures and properties

Diazadithio and diazadiseleno[8]circulenes were synthesized in good yields through a non-pyrolytic cyclization starting from nitrogen-bridged tetraphenylene.

Graphical abstract: Quasi-planar diazadithio and diazodiseleno[8]circulenes: synthesis, structures and properties
From the themed collection: Novel π-electron molecular scaffolds
Research Article

The synthesis, structure, and properties of 5,6,11,12-tetraarylindeno[1,2-b]fluorenes and their applications as donors for organic photovoltaic devices

Three new highly twisted 5,6,11,12-tetraarylindeno[1,2-b]fluorenes have been synthesized, characterized with X-ray analysis, and utilized as electron donors in organic photovoltaics.

Graphical abstract: The synthesis, structure, and properties of 5,6,11,12-tetraarylindeno[1,2-b]fluorenes and their applications as donors for organic photovoltaic devices
From the themed collection: Novel π-electron molecular scaffolds
Research Article

Polymerization of acetylene: polyynes, but not carbyne

Polymerization of acetylene in the presence of sterically-hindered endgroups leads to polyynes, but with lengths shorter than by stepwise syntheses.

Graphical abstract: Polymerization of acetylene: polyynes, but not carbyne
From the themed collection: Novel π-electron molecular scaffolds
Research Article

Synthesis of a figure-eight azahelicene dimer with high emission and CPL properties

A bisbutadiyne bridged azahelicene dimer with a figure-eight shape, which exhibited both high fluorescence quantum yield and CPL properties, has been synthesized through the Glaser–Hay homo-coupling reaction with diethynylazahelicene.

Graphical abstract: Synthesis of a figure-eight azahelicene dimer with high emission and CPL properties
From the themed collection: Novel π-electron molecular scaffolds
Open Access Research Article

Donor- and acceptor-functionalized dibenzo[a,e]pentalenes: modulation of the electronic band gap

The syntheses, and optoelectronic and structural properties of 2,7-donor- and acceptor-functionalized dibenzo[a,e]pentalenes, accessed in a versatile synthetic route, are presented and discussed.

Graphical abstract: Donor- and acceptor-functionalized dibenzo[a,e]pentalenes: modulation of the electronic band gap
From the themed collection: Novel π-electron molecular scaffolds
Open Access Research Article

Synthesis of a quinoidal dithieno[2,3-d;2′,3′-d]benzo[2,1-b;3,4-b′]-dithiophene based open-shell singlet biradicaloid

A fused heteroacene derivative, bis(dicyanomethylene)-end-capped-dithieno[2,3-d;2′,3′-d]benzo[2,1-b;3,4-b′]-dithiophene (4CN-DTmBDT) was synthesized.

Graphical abstract: Synthesis of a quinoidal dithieno[2,3-d;2′,3′-d]benzo[2,1-b;3,4-b′]-dithiophene based open-shell singlet biradicaloid
From the themed collection: Novel π-electron molecular scaffolds
Research Article

A cross-coupling-annulation cascade from peri-dibromonaphthalimide to pseudo-rylene bisimides

A novel synthetic strategy based on cascade C–C cross-coupling and C–H arylation afforded structurally unique polycyclic aromatics with desirable optical and redox properties.

Graphical abstract: A cross-coupling-annulation cascade from peri-dibromonaphthalimide to pseudo-rylene bisimides
From the themed collection: Novel π-electron molecular scaffolds
38 articles

About this collection

Novel pi-electron molecular scaffolds enable clarification of fundamental questions of chemical bonding and can also operate as functional materials for diverse applications such as fluorescence sensing, photoswitching, or organic electronics.

This themed collection aims to showcase the very recent efforts in designing exciting new structures, developing unprecedented synthetic methods, illustrating structure-property relationships, and also the investigations into (anti-)aromaticity, optical or redox properties, or conformational features of pi-electron systems.

Guest Editors of this themed collection are Professor Frank Würthner (University of Würzburg, Germany), Professor Michael Haley (University of Oregon, USA) and Professor Nazario Martín (University Complutense Madrid, Spain).

More articles will be added into this collection as soon as they are published.

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