Synfacts, Год журнала: 2021, Номер 18(01), С. 0034 - 0034
Опубликована: Дек. 17, 2021
Key words azahelicenes - optoelectronics luminescence arylpyridines
Язык: Английский
Synfacts, Год журнала: 2021, Номер 18(01), С. 0034 - 0034
Опубликована: Дек. 17, 2021
Key words azahelicenes - optoelectronics luminescence arylpyridines
Язык: Английский
Chem Catalysis, Год журнала: 2022, Номер 2(11), С. 3077 - 3111
Опубликована: Ноя. 1, 2022
Язык: Английский
Процитировано
42Nature Communications, Год журнала: 2023, Номер 14(1)
Опубликована: Июнь 8, 2023
Heterohelicenes are of increasing importance in the fields materials science, molecular recognition, and asymmetric catalysis. However, enantioselective construction these molecules, especially by organocatalytic methods, is challenging, few methods available. In this study, we synthesize enantioenriched 1-(3-indol)-quino[n]helicenes through chiral phosphoric acid-catalyzed Povarov reaction followed oxidative aromatization. The method has a broad substrate scope offers rapid access to an array quinohelicenes with enantioselectivities up 99%. Additionally, photochemical electrochemical properties selected explored.
Язык: Английский
Процитировано
33Angewandte Chemie International Edition, Год журнала: 2024, Номер 63(9)
Опубликована: Янв. 10, 2024
We report the helicoselective and convergent construction of indolohelicenoids with excellent efficiency stereocontrol. This reaction proceeds through a chiral-phosphoric-acid-catalyzed enantioselective cycloaddition eliminative aromatization sequence, which can be finely controlled by adjusting temperature. Mechanistic studies reveal that chiral phosphoric acid cooperatively serves as both bifunctional Brønsted catalyst, enabling one-pot central-to-helical chirality conversion. Additionally, optical properties synthesized were characterized to explore their potential applications in organic photoelectric materials.
Язык: Английский
Процитировано
9Cell Reports Physical Science, Год журнала: 2024, Номер 5(6), С. 101993 - 101993
Опубликована: Май 27, 2024
Incorporating main-group elements into the backbone of chiral carbohelicenes can significantly alter their electronic and optical properties, which renders asymmetric synthesis heterohelicenes an appealing research field. Herein, we present divergent two distinct types from same starting material by employing key Povarov reaction with phosphoric acid catalysts. Specifically, one-pot reaction/oxidative aromatization yielded C1-ortho-phenol-substituted [5]/[6]pyridohelicenes, while subsequent Pd(II)/base-mediated furan formation resulted in longer [7]/[8]heterohelicenes bearing both pyridine moieties. Fruitful derivatizations helicenes, along promising photophysical chiroptical have underscored value this method.
Язык: Английский
Процитировано
7ACS Catalysis, Год журнала: 2022, Номер 12(20), С. 13034 - 13041
Опубликована: Окт. 12, 2022
Enantioenriched pyrido[6]helicenes and furan-containing pyrido[7]helicenes have been synthesized through palladium-catalyzed double imidoylative cyclization by applying axially achiral multiaryl bisisocyanides aryl iodides as coupling components. Two pyridyl rings were constructed sequentially forming four C–C bonds in one pot with low catalyst loading. A control study using precyclized biaryl monoisocyanides revealed the second pyridine-forming enantiomer-generating step, which also enabled introduction of different substituents, including trifluoromethyl, on helical skeleton. This general convergent approach to structurally diversified optically pure pyridohelicenes paves way for optical studies potential applications this important class azahelicenes.
Язык: Английский
Процитировано
29The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(15), С. 11067 - 11071
Опубликована: Июль 23, 2024
An unprecedented divergent aromatization reaction of α-halobenzyl γ-butenolides has been described for the selective and concise synthesis highly substituted benzo higher π-extended fluorenones, 1,3-disubstituted naphthalenes depending on migration ability quaternary α-substituent. This switch from Ag
Язык: Английский
Процитировано
3Chemical Communications, Год журнала: 2025, Номер unknown
Опубликована: Янв. 1, 2025
This feature article summarizes the recent developments of azahelicenes showing circularly polarized luminescence.
Язык: Английский
Процитировано
0Journal of Luminescence, Год журнала: 2025, Номер unknown, С. 121328 - 121328
Опубликована: Май 1, 2025
Язык: Английский
Процитировано
0Angewandte Chemie International Edition, Год журнала: 2023, Номер 62(50)
Опубликована: Окт. 26, 2023
Oxidative fusion reaction of cyclic heteroaromatic pentads consisting pyrrole and thiophene gave closed-heterohelicene monomers dimers depending on the oxidation conditions. Specifically, with [bis(trifluoroacetoxy)iodo]benzene (PIFA) closed-[7]helicene connected at β-position one units remarkably elongated C-C bonds about 1.60 Å. Although this bond was intact against thermal physical activations, homolytic dissociation took place in DMSO upon irradiation UV light to give corresponding monomers. Thus, interconversion between closed-helicene monomer dimer achieved. The optically pure photo-dissociated into associated a turn-on circularly polarized luminescence (CPL).
Язык: Английский
Процитировано
8The Journal of Organic Chemistry, Год журнала: 2022, Номер 87(11), С. 7150 - 7166
Опубликована: Май 12, 2022
A series of aza[n]helicenes (n = 4-7) was synthesized using a photocyclodehydrochlorination 1-chloro-N-aryl-2-naphthamides as general synthetic procedure introducing the nitrogen atom to third ring helicene framework. The effect presence in skeleton on physicochemical properties prepared studied and compared those parent carbo-analogues. insertion into outer edge molecule has severe impact certain such optical rotation, electrostatic potentials, intermolecular interactions. On other hand, some UV/vis, fluorescence, phosphorescence spectra remained almost unaffected when carbohelicenes. can be also used for further derivatization, which lead modification properties, manifested here fluorescence changes induced by protonation.
Язык: Английский
Процитировано
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