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Themed collection Pi conjugated system bricolage (figuration) toward functional organic molecular systems

39 items
Review Article

Figuration of bowl-shaped π-conjugated molecules: properties and functions

Synthesis, properties, and functions of bowl-shaped pi-conjugated molecules including a hetero atom-doped system are reviewed.

Graphical abstract: Figuration of bowl-shaped π-conjugated molecules: properties and functions
Research Article

A meta-diisocyanide benzene-based aryl gold isocyanide complex exhibiting multiple solid-state molecular arrangements and luminescent mechanochromism

Research Article

A dendrimer emitter doped in a dendrimer host: efficient thermally activated delayed fluorescence OLEDs with fully-solution processed organic-layers

TADF OLEDs with fully solution-processed organic-layers with all dendrimer emitting layers that exhibit 16.1% external quantum efficiency.

Graphical abstract: A dendrimer emitter doped in a dendrimer host: efficient thermally activated delayed fluorescence OLEDs with fully-solution processed organic-layers
Research Article

Synthesis of bithiazole-based semiconducting polymers via Cu-catalysed aerobic oxidative coupling

A combination of direct arylation and aerobic oxidative coupling reactions enables a straightforward synthesis of semiconducting materials.

Graphical abstract: Synthesis of bithiazole-based semiconducting polymers via Cu-catalysed aerobic oxidative coupling
Research Article

Electronic properties of tin iodide hybrid perovskites: effect of indium doping

For solution-processable tin iodide cubic perovskites, a small amount of indium doping reduced the conductivity without changing the band gap or the carrier concentration. We demonstrated another possibility of foreign metal doping in tin iodide cubic perovskites and displayed a design strategy for electronic devices using hybrid perovskites.

Graphical abstract: Electronic properties of tin iodide hybrid perovskites: effect of indium doping
Research Article

Electron-transporting foldable alternating copolymers of perylenediimide and flexible macromolecular chains

Folding behaviours in solution, solid-state structure, and electron mobility are clarified for newly-synthesized alternating copolymers of perylenediimide and flexible chains.

Graphical abstract: Electron-transporting foldable alternating copolymers of perylenediimide and flexible macromolecular chains
Research Article

Highly efficient transformation of linear poly(phenylene ethynylene)s into zigzag-shaped π-conjugated microporous polymers through boron-mediated alkyne benzannulation

Linear poly(phenylene ethynylene)s are directly converted into zigzag-shaped π-conjugated microporous polymers.

Graphical abstract: Highly efficient transformation of linear poly(phenylene ethynylene)s into zigzag-shaped π-conjugated microporous polymers through boron-mediated alkyne benzannulation
Research Article

Theoretical study on the gigantic effect of external static electric field application on the nonlinear optical properties of 1,2,3,5-dithiadiazolyl π-radical dimers

The promising potential of π-radical dithiadiazolyl dimers as a novel class of highly-active external-field-driven NLO switches.

Graphical abstract: Theoretical study on the gigantic effect of external static electric field application on the nonlinear optical properties of 1,2,3,5-dithiadiazolyl π-radical dimers
Research Article

Synthesis of optically active π-stacked compounds based on planar chiral tetrasubstituted [2.2]paracyclophane

Optically active X-shaped compounds based on planar chiral [2.2]paracyclophane, consisting of two different π-electron systems stacked, were synthesized.

Graphical abstract: Synthesis of optically active π-stacked compounds based on planar chiral tetrasubstituted [2.2]paracyclophane
Research Article

Crystal structure and physical properties of radical cation salt based on 4,5-ethylenedioxy-4′-iodotetrathiafulvalene (EDO-TTF-I) with iodine bonding ability

The radical cation salt of 4,5-ethylenedioxy-4′-iodotetrathiafulvalene possessing iodine bonding ability afforded the β′-type molecular arrangement in dimerized Mott insulating state.

Graphical abstract: Crystal structure and physical properties of radical cation salt based on 4,5-ethylenedioxy-4′-iodotetrathiafulvalene (EDO-TTF-I) with iodine bonding ability
Research Article

High-efficiency ultrapure green organic light-emitting diodes

Efficient ultrapure green OLEDs were demonstrated by using a platinum complex (PtN7N) and a top emitting structure.

Graphical abstract: High-efficiency ultrapure green organic light-emitting diodes
Research Article

A helically-twisted ladder based on 9,9′-bifluorenylidene: synthesis, characterization, and carrier-transport properties

We synthesized a ladder-shaped 9,9′-bifluorenylidene cyclic dimer (CBF), in which the two 9,9′-bifluorenylidene units are connected directly with two covalent bonds.

Graphical abstract: A helically-twisted ladder based on 9,9′-bifluorenylidene: synthesis, characterization, and carrier-transport properties
Research Article

On-surface synthesis of graphene clusters from a Z-bar-linkage precursor with quaterphenyl branches

Graphene clusters were fabricated from a quaterphenyl-branched “Z-bar-linkage” precursor, following intramolecular and intermolecular fusion.

Graphical abstract: On-surface synthesis of graphene clusters from a Z-bar-linkage precursor with quaterphenyl branches
Research Article

Universality of the giant Seebeck effect in organic small molecules

Various pure organic semiconducting molecules exhibit extraordinarily large Seebeck coefficient which cannot be elucidated by conventional physical models of thermoelectricity.

Graphical abstract: Universality of the giant Seebeck effect in organic small molecules
Research Article

Pressure-induced Mott-insulator–metal crossover at ambient temperature in an overexpanded fulleride

The Mott-insulator–metal transition in A3C60 fullerides is traversed at ambient temperature through the application of external pressure.

Graphical abstract: Pressure-induced Mott-insulator–metal crossover at ambient temperature in an overexpanded fulleride
Research Article

An ester-substituted polyfluorene derivative for light-emitting electrochemical cells: bright blue emission and its application in a host–guest system

Ester substitution realized phase compatible film blends of a polymer and an ionic liquid for bright light-emitting electrochemical cells.

Graphical abstract: An ester-substituted polyfluorene derivative for light-emitting electrochemical cells: bright blue emission and its application in a host–guest system
Research Article

Thermal and optical properties of multiblock macrocycles with hysteretic polymorphic transition

The thermal phase transition properties of macrocyclic molecules 1 and 2 consisting of aromatic 1,4-bis(phenylethynyl)benzene (BPEB) components and tetraethylene glycol (TEG) chains were investigated.

Graphical abstract: Thermal and optical properties of multiblock macrocycles with hysteretic polymorphic transition
Research Article

Orbital-specific electronic interaction in crystalline films of iron phthalocyanine grown on Au(111) probed by angle-resolved photoemission spectroscopy

Orbital-specific electronic interaction as a key to understanding unique molecular electronic and magnetic properties.

Graphical abstract: Orbital-specific electronic interaction in crystalline films of iron phthalocyanine grown on Au(111) probed by angle-resolved photoemission spectroscopy
Research Article

Solid-state self-inclusion complexation behaviour of a pillar[5]arene-based host–guest conjugate

A host–guest conjugate consisting of a pillar[5]arene and an ethylene moiety containing a triazole group at one end and a perfluorooctyl group at the other end displayed unusual real-time scale solid-state self-inclusion complexation behaviour.

Graphical abstract: Solid-state self-inclusion complexation behaviour of a pillar[5]arene-based host–guest conjugate
Research Article

A phenol-fused tetrathiafulvalene: modulation of hydrogen-bond patterns and electrical conductivity in the charge-transfer salt

Elimination of one hydroxy group from a tetrathiafulvalene derivative changed hydrogen-bond patterns in the charge-transfer salt, leading to improved conductivity.

Graphical abstract: A phenol-fused tetrathiafulvalene: modulation of hydrogen-bond patterns and electrical conductivity in the charge-transfer salt
Research Article

A direct synthetic method for (nitronyl nitroxide)-substituted π-electronic compounds via a palladium-catalyzed cross-coupling reaction with a zinc complex

We have developed an efficient synthetic method for (nitronyl nitroxide)-substituted π-electronic compounds via palladium-catalyzed cross-coupling reactions with a zinc complex of the parent nitronyl nitroxide radical anion.

Graphical abstract: A direct synthetic method for (nitronyl nitroxide)-substituted π-electronic compounds via a palladium-catalyzed cross-coupling reaction with a zinc complex
Research Article

A circularly polarized luminescent organogel based on a Pt(II) complex possessing phenylisoxazoles

A CPL-active organogel was synthesized based on a helical stacked assembly of a Pt(II) phenylbipyridine complex possessing phenylisoxazoles.

Graphical abstract: A circularly polarized luminescent organogel based on a Pt(ii) complex possessing phenylisoxazoles
Research Article

Tris(2-hydroxyphenyl)triazasumanene: bowl-shaped excited-state intramolecular proton transfer (ESIPT) fluorophore coupled with aggregation-induced enhanced emission (AIEE)

Tris(2-hydroxyphenyl)triazasumanene ((A)-(+)-1), a bowl-shaped molecule, which possesses 2-(2′-hydroxyphenyl)pyridine moieties, was successfully synthesised.

Graphical abstract: Tris(2-hydroxyphenyl)triazasumanene: bowl-shaped excited-state intramolecular proton transfer (ESIPT) fluorophore coupled with aggregation-induced enhanced emission (AIEE)
Research Article

Rhodium-mediated enantioselective synthesis of a benzopicene-based phospha[9]helicene: the structure–property relationship of triphenylene- and benzopicene-based carbo- and phosphahelicenes

The enantioselective synthesis of a phospha[9]helicene with a bibenzopicene skeleton has been achieved via the rhodium-mediated intermolecular [2+2+2] cycloaddition of a binaphthyl-linked tetrayne with a phosphorus-linked diyne.

Graphical abstract: Rhodium-mediated enantioselective synthesis of a benzopicene-based phospha[9]helicene: the structure–property relationship of triphenylene- and benzopicene-based carbo- and phosphahelicenes
Research Article

Synthesis and properties of a twin donor molecule composed of cofacially stacked dihydrodiazapentacenes

A clip-shaped donor–acceptor–donor (D–A–D) molecule has been prepared with 6,13-dihydro-6,13-diazapentacene (DHDAP) as a building unit.

Graphical abstract: Synthesis and properties of a twin donor molecule composed of cofacially stacked dihydrodiazapentacenes
Research Article

Metamagnetism with TN = 97 K in a layered assembly of paddlewheel [Ru2] units and TCNQ: an empirical rule for interlayer distances determining the magnetic ground state

A new layered antiferromagnet was synthesized from the reaction of a paddlewheel diruthenium(II,II) complex with a TCNQ derivative. The complex has a short interlayer distance and forms part of a series of layered antiferromagnets.

Graphical abstract: Metamagnetism with TN = 97 K in a layered assembly of paddlewheel [Ru2] units and TCNQ: an empirical rule for interlayer distances determining the magnetic ground state
Research Article

Synthesis and properties of spiro-type heterasumanenes containing group 14 elements as bridging atoms

Spiro-type heterasumanenes composed of two triphenylenodithiophene units and group 14 bridging atoms were synthesized by stepwise lithiations of hexaalkoxytriphenylene derivatives and treatment with heteroatom reagents.

Graphical abstract: Synthesis and properties of spiro-type heterasumanenes containing group 14 elements as bridging atoms
Research Article

Use of silylmethoxy groups as inducers of efficient room temperature phosphorescence from precious-metal-free organic luminophores

Crystals of and PMMA films doped with 2,5-bis(silylmethoxy)-1,4-diaroylbenzenes exhibit efficient green phosphorescence at room temperature.

Graphical abstract: Use of silylmethoxy groups as inducers of efficient room temperature phosphorescence from precious-metal-free organic luminophores
Research Article

Sterically crowded hydrogen-bonded hexagonal network frameworks

TpMe and TpF with substituents at the ortho-positions of carboxy groups were synthesized and revealed substituent effects on molecular assembly.

Graphical abstract: Sterically crowded hydrogen-bonded hexagonal network frameworks
Research Article

Aggregation-responsive ON–OFF–ON fluorescence-switching behaviour of twisted tetrakis(benzo[b]furyl)ethene made by hafnium-mediated McMurry coupling

A new type of molecule tetrakis(benzo[b]furyl)ethene (TBFE) undergoes two-wavelength ON–OFF–ON three-stage fluorescence switching triggered by aggregation.

Graphical abstract: Aggregation-responsive ON–OFF–ON fluorescence-switching behaviour of twisted tetrakis(benzo[b]furyl)ethene made by hafnium-mediated McMurry coupling
Research Article

FRET-mediated near infrared whispering gallery modes: studies on the relevance of intracavity energy transfer with Q-factors

NIR WGM resonators are fabricated from energy-donating and accepting conjugated polymers.

Graphical abstract: FRET-mediated near infrared whispering gallery modes: studies on the relevance of intracavity energy transfer with Q-factors
Research Article

Hole-transporting materials based on thiophene-fused arenes from sulfur-mediated thienannulations

Thiophene-fused arenes were synthesized by sulfur-mediated simple thienannulation reactions and applied to hole-transporting materials in perovskite solar cells.

Graphical abstract: Hole-transporting materials based on thiophene-fused arenes from sulfur-mediated thienannulations
Research Article

Water-induced self-assembly of an amphiphilic perylene bisimide dyad into vesicles, fibers, coils, and rings

Bestowing amphiphilicity to specifically designed perylene bisimide dyads enables diverse self-assembly pathways in aqueous media.

Graphical abstract: Water-induced self-assembly of an amphiphilic perylene bisimide dyad into vesicles, fibers, coils, and rings
Research Article

Blackening of aza-BODIPY analogues by simple dimerization: panchromatic absorption of a pyrrolopyrrole aza-BODIPY dimer

Dimerization of the so-called pyrrolopyrrole aza-BODIPY via a bithienyl linkage led to the creation of a novel black dye with dual emission and panchromatic absorption properties in the Vis/NIR region.

Graphical abstract: Blackening of aza-BODIPY analogues by simple dimerization: panchromatic absorption of a pyrrolopyrrole aza-BODIPY dimer
Research Article

Control of the electrochemical and photophysical properties of N-substituted benzo[ghi]perylene derivatives

Orientation of the lone-pair of electron-dependent electrochemical and photophysical properties were successfully observed by using a series of N-substituted benzo[ghi]perylene derivatives.

Graphical abstract: Control of the electrochemical and photophysical properties of N-substituted benzo[ghi]perylene derivatives
Research Article

Direct amination of the antiaromatic NiII norcorrole

The introduction of amino-substituents to an antiaromatic NiII norcorrole complex was accomplished regioselectively upon simple treatment with various amines without any catalysts. The optical and electrochemical properties of the amino norcorroles were substantially modulated by electron-donating amino groups.

Graphical abstract: Direct amination of the antiaromatic NiII norcorrole
Chemistry Frontiers

Dynamic molecular assemblies toward a new frontier in materials chemistry

Dynamic molecular assemblies with protonic, ionic, and molecular motions can be coupled with intrinsic π-electronic functions, offering a new direction in the future of materials chemistry.

Graphical abstract: Dynamic molecular assemblies toward a new frontier in materials chemistry
Chemistry Frontiers

Synthesis and properties of open-cage fullerene C60 derivatives: impact of the extended π-conjugation

Novel open-cage fullerene C60 derivatives with extended π-conjugation bearing thiophene rings exhibit long wavelength absorption due to characteristic intramolecular charge transfer transitions.

Graphical abstract: Synthesis and properties of open-cage fullerene C60 derivatives: impact of the extended π-conjugation
Chemistry Frontiers

Single-molecule junctions of π molecules

An investigation on a single-molecule junction reveals the intrinsic properties of a π molecule without the effect of intermolecular interaction and also uncovers its unique properties.

Graphical abstract: Single-molecule junctions of π molecules
39 items

About this collection

Materials Chemistry Frontiers is delighted to publish the collection of articles on “Pi conjugated system bricolage (figuration) toward functional organic molecular systems”, guest edited by Takanori Fukushima (Tokyo Institute of Techonolgy) and Tomoyuki Akutagawa (Tohoku University).

π-Electronic molecules, displaying electronic, optical, and magnetic functions, have played critical roles not only in fundamental chemistry but also in diverse research areas from materials to life sciences. Aim of this themed collection is to showcase the very recent efforts in creating superb π-electronic materials and functions as well as exploring new phenomena based on the design concept of “π-figuration”. Topics include but are not limited to:

·         Development of novel molecular frameworks that provide the basis for the π-figuration concept by utilizing state-of-the-art organic synthesis

·         Development of functional π-electronic molecular assemblies at many length scales by utilizing state-of-the-art supramolecular and polymer chemistry

·         Prediction, design, and revelation of functions of the new π-electronic materials by utilizing state-of-the-art theory, computational, and measurement techniques

More articles will be added into the collection as soon as published.

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