Stabilization of radical ions and highly electron-deficient systems under ambient conditions is great significance. A new design concept presented that applies the multifaceted features phosphonium group to achieve isolation (a) first naphthalenediimide (NDI) ion [(1a•+)BPh4–] as single crystals (b) an ultra-electron-deficient NDI [(1a2+)2BF4–] having lowest LUMO level recorded for NDI, overwhelming formative tetracyanoquinodimethane (TCNQ) molecule. Both 1a•+ 1a2+ exhibit unprecedented...

This review article highlights the emergence of eclectic molecular design principles to realize remarkably strong electron deficient arylenediimide molecules, aspects their stability and associated applications.

The review presents an overview of the organic radicals that have been designed and synthesized recently, their magnetic properties are discussed. π-conjugated such as phenalenyl systems, functionalized nitronylnitroxides, benzotriazinyl, bisthiazolyl, aminyl-based polyradicals, Tetrathiafulvalene (TTF)-based H-bonded considered. examples show weak supramolecular interactions play a major role in modulating ferromagnetic antiferromagnetic properties. new emerging direction zethrenes,...

Abstract Reported herein is the first isolation of tetracyano‐naphthalenediimide [NDI(CN) 4 ] and its radical anion, structural elucidation through spectroscopic X‐ray diffraction studies. The anion shows remarkable stability was purified by chromatography, which unique for planar anions. results from multiple hydrogen bonds to counter ion an array intramolecular noncovalent interactions. revealed one strongest NDI π–π interactions (3.268 Å). Electrochemical studies confirm extraordinarily...

The synthesis and isolation of an ambient stable perylenediimide radical anion is reported, its precursor established as one the strongest electron acceptors. shows absorption up to 1400 nm in mixed aqueous solution. Interestingly, can organize two electron-deficient molecules over surface form a π-stacked array. Calculations revealed weak spin polarization via noncovalent interactions. Such interactions are significance for magnetic exchange catalysis.

Green synthetic routes to a library of twenty four diphosphonium substituted naphthalenediimide (NDI) radical ions [NDI(PR₃)₂]˙⁺ Br⁻ (R = alkyl/aryl) with excellent yields and stability are reported.

A facile synthesis of octabromoperylene-3,4,9,10-tetracarboxylic dianhydride (Br8-PDA) (1), its diimides (Br8-PDIs) (2a–e), and bis-, tris-, tetra-amino substituted (5a–c) with six, five, four remaining substitutable Br atoms, respectively, is reported. Octabromination results in chemical/electrochemical reduction, radical anion formation, red-shifted optical properties. For the first time, diverse halogen-bonding interactions were identified PDA/PDI, which along attractive electronic...

An unprecedented visible light-assisted and zinc triflate-catalyzed construction of a diaryl-substituted quaternary stereocenter is reported. 2-(4-Hydroxyphenyl)-substituted aldehydes ketones have been prepared in moderate to high yields via multicomponent reaction acetylene, benzoquinone (BQ), indole/aniline/thiol. The believed proceed situ generation p-quinone methide through [2+2] cycloaddition–retroelectrocyclization BQ acetylene blue light followed by vinylogous Michael addition with...

The synthesis and isolation of two-electron reduced naphthalenediimides is reported. A doubly zwitterionic structure observed for the first time in a naphthalene moiety, which aids its stabilization.

A tandem cleavage of carbon-carbon and carbon-nitrogen bonds in imidazo[1,2-a]pyridines imidazo[1,2-a]quinolines is reported the presence eosin Y visible light. The ring opening occurs under ambient conditions through singlet oxygen insertion, bond CO2 elimination, produces N-(pyridin-2-yl) amides N-(quinolin-2-yl) high yields. reaction shows good versatility, does not require strong external oxidants additives.

Abstract Reported herein is the first isolation of tetracyano‐naphthalenediimide [NDI(CN) 4 ] and its radical anion, structural elucidation through spectroscopic X‐ray diffraction studies. The anion shows remarkable stability was purified by chromatography, which unique for planar anions. results from multiple hydrogen bonds to counter ion an array intramolecular noncovalent interactions. revealed one strongest NDI π–π interactions (3.268 Å). Electrochemical studies confirm extraordinarily...

A C‐3 thiocyanation of 2‐aryl‐quinolin‐4‐ones in the presence eosin‐Y and visible light has been developed. The methodology allows easy access to a variety 2‐aryl‐3‐thiocyano‐quinolin‐4‐ones moderate high yields. Regioselective para ‐thiocyanation anilines also achieved under these conditions. reaction is operationally simple, metal‐free, requires air as oxidant, proceeds smoothly at room temperature.

Antimalarial drug resistance is a serious obstacle in the persistent quest to eradicate malaria. There need for potent chemical agents that are able act on drug-resistant Plasmodium falciparum populations at reasonable concentrations without any related toxicity host. By rational design, we envisaged address this issue by generating novel hybrid possessing two pharmacophores can unique and independent targets within cell. We synthesized new class of ciprofloxacin-based molecules, which have...

An unprecedented visible light mediated regioselective C-3 halogenation of quinolones was achieved using halo-fluorescein dyes as a halogen source and air an oxidant. This reaction has broad substrate scope gives 3-halo quinolone derivatives.

Synthesis to enhance the electron donor ability of organic radicals has not been attempted due reactivity challenges. Herein, naphthalenediimide-based (NDI•±) zwitterionic are synthesized and isolated bestowing SOMO levels up -4.04 eV. As a result, reduction NDI is realized with NDI•± in their ground states. Notably, unit applying π-electron unprecedented limited inorganic/organometallic reagents or by light-driven excited

π-acidic boxes exhibiting electron reservoir and proton conduction are unprecedented because of their instability in water. We present the synthesis one strongest electron-deficient ionic showing e- uptake as well conductivity. Two large anions fit box to form anion-π interactions infinite anion-solvent wires. The with NO3-···water wires confers high conductivity presents first example that manifests redox functionality an organic macrocycle.

Abstract Electron‐rich π‐conjugated dianions are known to be ambient unstable and their stabilization in water is yet realized. We report the first example of an exceptionally stable naphthalenediimide‐based dianion hot water, forming one most redox‐active dianion. The half‐life ( t 1/2 ) 1 a 2− more than four months water. dianionic state was confirmed by X‐ray crystallography various spectroscopic methods. noncovalent electronic conduits introduced for time dianions, embrace n O → π * C≡N...

An ambient stable pyreno[4,5- b ]pyrrole monoanion and :9,10- ′]dipyrrole dianion have been isolated characterized, showing a low energy intense absorption band with the coefficient reaching 7.1 × 10 4 dm 3 mol −1 cm .

Abstract The preparation of a new class electron deficient organic compounds is great interest for the development high‐performance n‐type semiconductors. Herein, facile synthetic protocol isolation first examples truxenone triimide (TTI) reported. electrochemical analysis resulting TTIs confirms that multi‐imidization helps in lowering LUMO energy level, tailoring prerequisite optoelectronic and/or semiconducting properties. Their microscopic charge carrier transport properties and dynamics...

Abstract Organic spin‐based molecular materials are considered to be attractive for the generation of functional with emergent optoelectronic, magnetic, or magneto‐conductive properties. However, major limitations utilization organic systems their high reactivity, instability, and propensity dimerization. Herein, we report synthesis, characterization, magnetic electronic studies three ambient stable radical ions ( 1 a .+ , b c ). The BPh 4 − BF counter anions, respectively, were synthesized...