Nucleophilic substitution of 9,10-dichlorooctafluoroanthracene with 3,4-diethylpyrrole and subsequent Scholl reaction give the annularly fused decapyrrollyl anthracene. Single crystal X-ray analysis revealed a highly contorted geometry induced by combination adjacent heptagons, forming unique 7-7-6-7-7 topology. The end-to-end twist angle along acene moiety is 90°. Cyclic voltammetry studies reveal 6-electron oxidation waves. Density functional theory calculations provided further insights...

The connection between magnetic field induced optical activity and chirality has a rich complicated history. Although the broken inversion symmetry of chiral molecules generates ‘natural’ activity, is generated by breaking time reversal symmetry. As result, molecular not expected to influence phenomena, such as Faraday rotation. Here we show that supramolecular assembly polymers can result in large effect. This strong rotation, which amongst highest value known for organic materials,...

Abstract Vinyl triazenes were obtained by enantioselective [2+2] cycloaddition reactions of bicyclic alkenes with 1‐alkynyl in the presence a Ru II catalyst chiral cyclopentadienyl ligand. These serve as unique vinyl cation surrogates. Under acidic conditions, triazene functionality can be replaced variety groups, including halides, alkoxides, sulfoxides, amides, arenes, and heteroarenes, thus providing efficient access to pool polycyclic compounds.

In this paper, we report redox-active azacoronene helicenes obtained through nucleophilic substitution of fluorinated with 3,4-diethylpyrrole, followed by Scholl reactions. Cyclic voltammetry these compounds displays reversible oxidation events at low potentials. The oxidized species display distinct optical properties. Additionally, incorporated the azacoronene/helicene unit into conjugated polymers.

A simple and versatile method for the preparation of linear, trisubstituted triazenes is reported. The procedure based on reaction Grignard reagents with 1-azido-4-iodobutane or 4-azidobutyl-4-methylbenzenesulfonate. These organic azides enable regioselective formation via an intramolecular cyclization step. new can be used aryl, heteroaryl, vinyl, alkyl triazenes. synthetic utility vinyl demonstrated by acid-induced C–N, C–O, C–F, C–P, C–S bond-forming reactions.

Tetraarylethenes are obtained by acid-induced coupling of vinyl triazenes with aromatic compounds. This new C-H activation route for the synthesis aggregation-induced emission luminogens is simple, fast, and versatile. It allows direct grafting triarylethenyl groups onto a variety compounds, including heterocycles, supramolecular hosts, biologically relevant molecules, commercial polymers.

Donor–acceptor cyclopropanes substituted with 3,3-dialkyltriazenyl groups are described herein. The strong electron-donating character of the triazene renders highly reactive, allowing for catalyst-free ring-opening reactions methanol and tetracyanoethylene under mild conditions. triazene-substituted could also be used as substrates in Lewis acid catalyzed (3 + 2) annulations silyl enol ethers.

Abstract Vinyl triazenes were obtained by enantioselective [2+2] cycloaddition reactions of bicyclic alkenes with 1‐alkynyl in the presence a Ru II catalyst chiral cyclopentadienyl ligand. These serve as unique vinyl cation surrogates. Under acidic conditions, triazene functionality can be replaced variety groups, including halides, alkoxides, sulfoxides, amides, arenes, and heteroarenes, thus providing efficient access to pool polycyclic compounds.

Abstract Vinyl triazenes are potentially interesting compounds for synthetic organic and medicinal chemistry, but routes to make olefins with triazene groups still scarce. In this work, we show that vinyl accessible by Pd‐catalyzed addition reactions alkynyl triazenes. Hydrogenation, hydroarylation, haloallylation allow preparing mono‐, di‐ trisubstituted in high yields, good regio‐ stereoselectivities. magnified image

The synthetic utility of triazenes rests on the fact that triazene function can be cleaved by Brønsted or Lewis acids, liberating diazonium compounds. However, preferred coordination site acid is still a matter debate. We have analyzed triflic acid, B(C6F5)3, and PdCl2 adducts NMR spectroscopy single crystal X-ray crystallography. In all cases, we observe to N1 atom triazene. This finding not only relevance for acid-induced cleavage reactions, but also metal-catalyzed reactions with...

Abstract Tetraarylethenes are obtained by acid‐induced coupling of vinyl triazenes with aromatic compounds. This new C−H activation route for the synthesis aggregation‐induced emission luminogens is simple, fast, and versatile. It allows direct grafting triarylethenyl groups onto a variety compounds, including heterocycles, supramolecular hosts, biologically relevant molecules, commercial polymers.

Highly substituted Δ3 -1,2,3-triazolines can be prepared by reaction of triarylvinyl Grignard reagents with functionalized organic azides. The heterocycles are fluorescent in the solid state, and-depending on substituents-they display aggregation-induced emission. Upon oxidation, triazolines form stable radical cations altered photophysical properties. Therefore, they represent rare examples solid-state emitters intrinsic electrofluorochromic behavior.

Abstract The aggregation‐induced emission properties of tetraarylethenes (TAEs) have led to numerous applications in chemistry, biology, and materials science. Herein, we describe two fluorinated tetraarylethenes, which can be employed as universal tags for the synthesis solid state luminogens. are accessible one or steps from commercially available starting materials. Facile coupling reactions with ubiquitous substrates such thiols, alcohols, amines, phosphines, aldehydes, enamines allow...

1,11-Dien-6-ynes undergo cycloisomerization in the presence of cobalt catalytic system CoBr 2 /phosphine ligand/Zn/ZnI giving cyclohexene, diene or cyclopropane structures depending on type phosphine ligand. This unpredictable behaviour suggests that, although availability is appealing, development well-defined catalysts desirable for further progress.

Borylated triazenes were synthesized by the dehydrocoupling of with 9-borabicyclo(3.3.1)nonane, condensation BEt3, or reaction sodium triazenides dialkyl- diarylboron halides. The structures products found to depend on size substituents. Sterically demanding mesityl groups at boron nitrogen gave rise open-chain structures, whereas smaller substituents led formation novel BN3 heterocycles.

Abstract Dichalcogenolenes are archetypal redox non‐innocent ligands with numerous applications. Herein, a diselenolene ligand fundamentally different electronic properties is described. A mesoionic was prepared by selenation of C2‐protected imidazolium salt. This diamagnetic, which in contrast to the paramagnetic nature standard dichalcogenolene monoanions. The new also redox‐active, as demonstrated isolation stable radical dianion. unique give rise unusual coordination chemistry. Thus,...

Abstract The aggregation‐induced emission properties of tetraarylethenes (TAEs) have led to numerous applications in chemistry, biology, and materials science. Herein, we describe two fluorinated tetraarylethenes, which can be employed as universal tags for the synthesis solid state luminogens. are accessible one or steps from commercially available starting materials. Facile coupling reactions with ubiquitous substrates such thiols, alcohols, amines, phosphines, aldehydes, enamines allow...

Abstract Aromatic compounds containing triazenyl groups (N 3 RR′) have a profound impact on synthetic organic and medicinal chemistry. In contrast, the chemistry of vinyl alkynyl triazenes was largely uncharted territory until recently. The situation has changed over last five years, it become apparent that are highly interesting with unique reactivity. electron‐donating properties group provide an ynamide‐like reactivity, which can be exploited in reactions triple bond. Vinyl triazenes,...