Constantin G. Daniliuc
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View article: Boron-Enabled Stereoselective Synthesis of Polysubstituted Housanes
Boron-Enabled Stereoselective Synthesis of Polysubstituted Housanes Open
The efficient design of (C)sp3-rich molecular scaffolds with defined exit vectors is central to expanding drug-like chemical space. Here, we report a boron-enabled strategy for the synthesis of polysubstituted housanes from nonsymmetrical …
View article: TADF Emission in Supramolecular Assemblies through Cooperativity and Polymorphism
TADF Emission in Supramolecular Assemblies through Cooperativity and Polymorphism Open
Supramolecular assemblies exhibiting thermally activated delayed fluorescence (TADF) represent a still poorly explored field of research. Here, the photophysical properties of a novel anthraquinone‐based dye 1 emitting in a wide range betw…
View article: Reaktion von Blatter‐ und Verdazyl‐Radikalen mit Arinen: Synthese und Untersuchung N‐chiraler, antiaromatischer Triazine und Tetrazinone
Reaktion von Blatter‐ und Verdazyl‐Radikalen mit Arinen: Synthese und Untersuchung N‐chiraler, antiaromatischer Triazine und Tetrazinone Open
Zusammenfassung Arine sind vielseitige Bausteine in der organischen Chemie. Im Gegensatz zu ihrer umfassend untersuchten ionischen Reaktivität sind radikalische Reaktionen mit Arinen noch kaum erforscht. Wir stellen hier eine neue radikali…
View article: Reaction of Blatter and Verdazyl Radicals with Arynes: Synthesis and Investigation of N‐Chiral, Antiaromatic Triazines, and Tetrazinones
Reaction of Blatter and Verdazyl Radicals with Arynes: Synthesis and Investigation of N‐Chiral, Antiaromatic Triazines, and Tetrazinones Open
Arynes are versatile building blocks in organic chemistry. In contrast to their extensively examined ionic reactivity, radical reactions with arynes remain scarcely explored. In this study, we present a novel radical annulation reaction of…
View article: Formal pyridine meta-azidation and its application for the synthesis of diazepines, ring-fused δ-carbolines and 1,2,3-triazolylpyridines
Formal pyridine meta-azidation and its application for the synthesis of diazepines, ring-fused δ-carbolines and 1,2,3-triazolylpyridines Open
The nitrogen atom serves as an important structural element in pharmacologic studies, highlighting the critical role of nitrogen-containing heterocycles in drug discovery. Late-stage peripheral functionalization and structural editing of n…
View article: Modular Amphiphilic Design Enables Control of Oblique vs J‐Type Exciton Coupling in Aqueous Self‐Assembly
Modular Amphiphilic Design Enables Control of Oblique vs J‐Type Exciton Coupling in Aqueous Self‐Assembly Open
Molecular design strategies are essential for rationalizing the aqueous self‐assembly behavior of π ‐conjugated amphiphilic molecules and for clarifying the relationship between their photophysical properties and nanostructure morphology. …
View article: Difluorinative Cyclopropene Rearrangement by I(I)/I(III) Catalysis: Regio‐ and Stereoselective Synthesis of Allyl Difluorides
Difluorinative Cyclopropene Rearrangement by I(I)/I(III) Catalysis: Regio‐ and Stereoselective Synthesis of Allyl Difluorides Open
Allyl difluorides are pervasive in the pharmaceutical arena, but synthetic challenges in the construction of highly substituted derivatives impede chemical space exploration. Consequently, efforts to develop general approaches that display…
View article: Difluorinative Cyclopropene Rearrangement by I(I)/I(III) Catalysis: Regio‐ and Stereoselective Synthesis of Allyl Difluorides
Difluorinative Cyclopropene Rearrangement by I(I)/I(III) Catalysis: Regio‐ and Stereoselective Synthesis of Allyl Difluorides Open
Allyl difluorides are pervasive in the pharmaceutical arena, but synthetic challenges in the construction of highly substituted derivatives impede chemical space exploration. Consequently, efforts to develop general approaches that display…
View article: Chiral pool synthesis of enantiomerically pure morphan derivatives with κ receptor affinity from (S)-perillaldehyde
Chiral pool synthesis of enantiomerically pure morphan derivatives with κ receptor affinity from (S)-perillaldehyde Open
Ethylenediamines represent a promising class of κ receptor agonists. Recently, the first ethylenediamine - morphan hybrid 4 with high κ receptor affinity, but poor selectivity over the σ1 receptor was reported. Herein, the chiral pool synt…
View article: <i>closo</i>‐Carboranyl Analogs of β‐Arylethylamines: Direct Synthesis from Alkenes via EnT‐Catalysis
<i>closo</i>‐Carboranyl Analogs of β‐Arylethylamines: Direct Synthesis from Alkenes via EnT‐Catalysis Open
closo ‐Carboranes are icosahedral carbon–boron clusters with unique properties and broad applicability. They particularly stand out in the context of drug development as privileged structural motifs for boron neutron capture therapy (BNCT)…
View article: Iron-catalysed radical Markovnikov hydroamidation of complex alkenes
Iron-catalysed radical Markovnikov hydroamidation of complex alkenes Open
Nitrogen atoms are integral components of various chemical functional groups, including amines, amides and N-heterocycles, among others. Consequently, they play an important role in pharmaceuticals, agrochemicals, natural products, materia…
View article: Cyclic Bifunctional Reagents Enabling a Strain-Release-Driven Formal [3 + 2] Cycloaddition of 2<i>H</i>-Azirines by Cascade Energy Transfer
Cyclic Bifunctional Reagents Enabling a Strain-Release-Driven Formal [3 + 2] Cycloaddition of 2<i>H</i>-Azirines by Cascade Energy Transfer Open
The energy transfer (EnT)-catalyzed ring opening and further decarboxylation of isoxazole-5(4H)-ones enables the in situ generation of strained 2H-azirines. Subsequent selective C(sp2)-C(sp3) bond cleavage of the azirine intermediate allow…
View article: Phenothiazine Sulfoxides as Active Photocatalysts for the Synthesis of γ-Lactones
Phenothiazine Sulfoxides as Active Photocatalysts for the Synthesis of γ-Lactones Open
N-substituted phenothiazines are prominent and highly effective organic photoredox catalysts, particularly known for their strong reducing capabilities. Despite their wide utility, the closely related phenothiazine sulfoxides, which easily…
View article: Size‐Controlled Self‐Assembly for Bimodal In Vivo Imaging
Size‐Controlled Self‐Assembly for Bimodal In Vivo Imaging Open
Contrast agents (CAs) are essential in biomedical imaging to aid in the diagnosis and therapy monitoring of disease. However, they are typically restricted to one imaging modality and have fixed properties such as size, shape, toxicity pro…
View article: Size‐Controlled Self‐Assembly for Bimodal In Vivo Imaging
Size‐Controlled Self‐Assembly for Bimodal In Vivo Imaging Open
Contrast agents (CAs) are essential in biomedical imaging to aid in the diagnosis and therapy monitoring of disease. However, they are typically restricted to one imaging modality and have fixed properties such as size, shape, toxicity pro…
View article: The Effect of Regioisomerism on the TADF Properties of Organic Dyes
The Effect of Regioisomerism on the TADF Properties of Organic Dyes Open
The properties of thermally activated delayed fluorescence (TADF) chromophores are highly dependent on the molecular design. The choice of the donor (D) and acceptor (A) group are as important as the choice of the π ‐linker and the substit…
View article: Deconjugative Photoisomerization of Cyclic Enones
Deconjugative Photoisomerization of Cyclic Enones Open
The deconjugative isomerization of α,β-unsaturated carbonyl compounds enables regioisomeric products to be forged with simultaneous Umpolung of alkene reactivity. Although highly enabling, the endergonic nature of the net process coupled w…
View article: Stereoselective Synthesis and Biological Evaluation of Perhydroquinoxaline-Based κ Receptor Agonists
Stereoselective Synthesis and Biological Evaluation of Perhydroquinoxaline-Based κ Receptor Agonists Open
The hydroxylated perhydroquinoxaline 14 was designed by conformational restriction of the prototypical κ receptor agonist U-50,488 and the introduction of an additional polar group. The synthesis of 14 comprised ten reaction steps starting…
View article: Diastereoselective 1,3-nitrooxygenation of bicyclo[1.1.0]butanes
Diastereoselective 1,3-nitrooxygenation of bicyclo[1.1.0]butanes Open
Diastereoselective 1,3-nitrooxygenation of bicyclo[1.1.0]butanes with tert -butylnitrite and TEMPO to access 1,1,3-trisubstituted cyclobutanes is reported.
View article: Mechanistic insights into the regiodivergent insertion of bicyclo[1.1.0]butanes towards carbocycle-tethered N-heteroarenes
Mechanistic insights into the regiodivergent insertion of bicyclo[1.1.0]butanes towards carbocycle-tethered N-heteroarenes Open
Cyclobutane-tethered N-heteroarenes are obtained via regio- and diastereoselective insertion of BCBs into C–S bonds of C2-thioether aza-arenes. Mechanistic and DFT studies reveal the activation mode and regiodivergence.
View article: Functionalization and solubilization of polycyclic aromatic compounds by sulfoniumization
Functionalization and solubilization of polycyclic aromatic compounds by sulfoniumization Open
A regioselective sulfoniumization of polycyclic aromatic hydrocarbons is described. The obtained sulfonium-salts, soluble in organic and water media, are employed in post-functionalizations, π-extension, and mitochondria-selective bio-imag…
View article: Lewis acid-catalyzed [2π+2σ] cycloaddition of dihydropyridines with bicyclobutanes
Lewis acid-catalyzed [2π+2σ] cycloaddition of dihydropyridines with bicyclobutanes Open
Herein we report a simple BF 3 -catalyzed cycloaddition of dihydropyridines with bicyclobutanes for the expedient synthesis of novel three-dimensional azacycle-fused bicyclo[2.1.1]hexane scaffolds.
View article: Steric pressure in heteropentacenes modulates the photophysical properties – a molecular design strategy for functional materials
Steric pressure in heteropentacenes modulates the photophysical properties – a molecular design strategy for functional materials Open
Steric pressure induced by methyl groups modulates the emissive states (solution to solid) and colors (red to green) of heteropentacyclic luminophores for sensing applications.
View article: Boron-Enabled Stereoselective Synthesis of Polysubstituted Housanes
Boron-Enabled Stereoselective Synthesis of Polysubstituted Housanes Open
The efficient design of (C)sp 3 -rich molecular scaffolds with defined exit vectors is central to expanding drug-like chemical space. Here, we report a boron-enabled strategy for the synthesis of polysubstituted housanes from nonsymmetric…