Abstract The first rational synthesis of a BN‐doped coronene derivative in which the central benzene ring has been replaced by borazine core is described. This includes six C−C ring‐closure steps that, through intramolecular Friedel–Crafts‐type reactions, allow stepwise planarization hexaarylborazine precursor. UV/Vis absorption, emission, and electrochemical investigations show that introduction BN induces dramatic widening HOMO–LUMO gap an enhancement blue‐shifted emissive properties with...

The synthesis and isolation of one the few examples a π-extended diamagnetic phenazine dication have been achieved by oxidizing phenanthrene-based dihydrophenazine precursor. resulting was isolated fully characterized, highlighting an aromatic distorted structure, generated conformational change upon oxidation precursor, which is also correlated with marked electrochromic in UV–vis spectrum. aromaticity has investigated theoretically, proving that species based on all major criteria...

Abstract White‐light‐emitting electrochemical cells (WLECs) still represent a significant milestone, since only few examples with moderate performances have been reported. Particularly, multiemissive white emitters are highly desired, as paradigm to circumvent phase separation and voltage‐dependent emission color issues that encountered following host:guest multilayered approaches. Herein, the origin of exclusive ternary electroluminescent behavior BN‐doped nanographenes B 3 N doping pattern...

In this work, a comprehensive account of the authors' synthetic efforts to prepare borazino-doped hexabenzocoronenes by using Friedel-Crafts-type electrophilic aromatic substitution is reported. Hexafluoro-functionalized aryl borazines, bearing an ortho fluoride leaving group on each N- and B-aryl rings, was shown lead cascade-type events in stepwise C-C bond formation, giving higher yields borazinocoronenes than those obtained with borazine precursors groups at positions substituents. By...

Self-heating in light-emitting electrochemical cells (LECs) has been long overlooked, while it a significant impact on (i) device chromaticity by changing the electroluminescent band shape, (ii) efficiency because of thermal quenching and exciton dissociation reducing external quantum (EQE), (iii) stability degradation excitons eliminate doped species, phase separation, collapse intrinsic emitting zone. Herein, we reveal, for first time, direct relationship between self-heating early changes...

The replacement of carbon atoms at the zigzag periphery a benzo[fg]tetracenyl derivative with an NBN atomic triad allows formation heteroatom-doped polycyclic aromatic hydrocarbon (PAH) isosteres, which expose BN mimics amidic NH functions. Their ability to form H-bonded complexes has never been touched so far. Herein, we report first solution recognition studies peripherally NBN-doped PAHs DD·AA- and ADDA·DAAD-type suitable complementary H-bonding acceptor partners. determination Ka in...

In this work, the synthesis of an N-monoarylated dihydrophenazine is reported together with its interconversion to oxidized mono-cationic form. While reduced state was employed for dechlorination aromatic substrates, one exploited formation C-N bonds between aryl rings and azoles, which achieved high yields very low catalyst loadings (down 0.5 mol%).

Redox-switchable Polymers of Intrinsic Microporosity (PIMs) are a promising yet underexplored class materials. Here, we introduce π-extended dihydrophenazine-based PIMs for gas separation. The tert-butyl substituted Phen-PIM-1 stands out as...

Abstract In recent years, organic chemists have devoted a great deal of effort towards the implementation novel green photocatalytic synthetic protocols. To this end, development new effective, non‐toxic, inexpensive photocatalysts, which are capable driving value‐added chemical transformations, is highly desirable. Interestingly, phenols fulfill all these requirements due to their outstanding physicochemical features, therefore emerging as promising metal‐free platforms for synthesis. This...

Abstract The first rational synthesis of a BN‐doped coronene derivative in which the central benzene ring has been replaced by borazine core is described. This includes six C−C ring‐closure steps that, through intramolecular Friedel–Crafts‐type reactions, allow stepwise planarization hexaarylborazine precursor. UV/Vis absorption, emission, and electrochemical investigations show that introduction BN induces dramatic widening HOMO–LUMO gap an enhancement blue‐shifted emissive properties with...

A light-driven protocol for the synthesis of 2,3-dihydrobenzofurans under mild conditions is reported. Specifically, cascade process initiated by photochemical activity allyl-functionalized phenolate anions, generated in situ upon deprotonation corresponding phenols. The reaction proceeds rapidly with times as low 35 min, delivering a wide range densely functionalized products (20 examples, yields up to 69%). Mechanistic studies have also been performed providing convincing evidence...

Herein, we describe the synthesis of first boron nitride-doped polyphenylenic material obtained through a [4 + 2] cycloaddition reaction between triethynyl borazine unit and biscyclopentadienone derivative, which undergoes organogel formation in chlorinated solvents (the critical jellification concentration is 4% w/w CHCl3). The polymer has been characterized extensively by Fourier-transform infrared spectroscopy, solid-state 13C NMR, 11B comparison with isolated monomeric unit. Furthermore,...

A light-driven metal-free protocol for the synthesis of sulfone-containing indoles under mild conditions is reported. Specifically, process driven by photochemical activity halogen-bonded complexes formed upon complexation a sacrificial donor, namely 1,4-diazabicyclo[2.2.2]octane (DABCO), with α-iodosulfones. The reaction provides variety densely functionalized products in good yields (up to 96% yield). Mechanistic investigations are These studies provide convincing evidences formation...

Abstract Dihydrophenazines are receiving increasing attention due to applications in numerous fields of chemistry, from light emission organo‐photocatalysis. Despite this growing interest and works involving the preparation radical cations based on scaffold, isolation study aromatic dications obtained by 2 electron oxidation dihydrophenazines is still mostly unexplored. From point view, along with substitution at N atoms generally used tune dihydrophenazine properties, π‐extension phenazine...

Building on the MOF approach to prepare porous materials, herein we report engineering of BN-doped materials using tricarboxylic hexaarylborazine ligands, which are laterally decorated with functional groups at full-carbon 'inner shell'. Whilst an open 3D entangled structure could be obtained from double interpenetration two identical metal frameworks derived methyl substituted borazine, chlorine-functionalised linker undergoes formation a layered 2D honeycomb structure, as shown by...

Here we describe the synthesis and spectroscopic structural characterization of various borazine-doped polyphenylenes displaying high doping dosages (16-18%). Capitalizing on condensation reaction approach, desired products were formed using a mixture p-phenylendiamine aniline with BCl3, followed by addition an aryl lithium derivative. The use mesityl (MesLi) yields strained multiborazine derivatives, which proved to be unstable in presence moisture. However, when xylyl (XylLi) was used,...

In this paper, the synthesis of a novel tetra-phenol π-extended dihydrophenazine is reported. The obtained derivative presents marked reducing properties in excited state and was exploited as an organo-photocatalyst dehalogenation C-C bond formation reactions. These results underline great potential functionalized dihydrophenazines organo-photocatalysts.

This paper discusses hyperconjugative stereoelectronic effects in borazines. A series of alkyl-substituted borazines were synthesized and analysed by NMR spectroscopy X-ray diffraction. Supported NBO analyses, the significant decreases

We present a combined approach integrating chemical synthesis, computational methods and advanced ultrafast spectroscopy to explore the properties of triphenodioxazine diimides (TPDODI). The TPDODI derivative shows significant redshifted absorption (λmax...

In article number 1906830, Rubén D. Costa and co-workers report the exclusive emission behaviour of BN-doped nanographenes with B3N3 doping pattern, leading to one most efficient stable white light-emitting electrochemical cells. This pattern provides electroluminescence spanning whole visible range. temperature-dependent multiemissive mechanism is operative for both photo- processes holds over device lifespan, regardless architecture, active layer composition, operating conditions.