Isolation of a 1,4-diketone intermediate in oxidative dimerization of 2-hydroxyanthracene and its conversion to oxahelicene

Matsuno, Takashi; Koyama, Yutaro; Hiroto, Satoru; Kumar, Jatish; Kawai, Tsuyoshi; Shinokubo, Hiroshi

doi:10.1039/c5cc00764j

Cited by 49 publications

(21 citation statements)

References 32 publications

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“…Given both the large number of reported CPL‐active [ n ]helicenes and also their quite diverse structural motifs (Scheme 4), we shall distinguish and base the discussion of the surveyed compounds on five main classes: 1) purely monomeric organic [ n ]helicenes (in turn divided into 6 subclasses according to n, with n being the number of aromatic units forming the helicene scaffold); [38–65] 2) dimeric systems; [48, 50, 66–68] 3) S‐shaped systems; [69, 70] 4) systems with semimetals (B and Si) in the [ n ]helicenes core or directly linked to it; [71–76] and 5) cationic systems [77–80] (Scheme 4 and Table 4).…”

Section: Cpl Emittersmentioning

confidence: 99%

Quantifying the Overall Efficiency of Circularly Polarized Emitters

Arrico

Bari

Zinna

2020

Chemistry A European J

396

409

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An increasing number of circularly polarized luminescence (CPL) molecular emitters has been developed in recent years and many of them are intended for applications in which high overall CPL efficiencies are required. In order to have a complete picture of the efficiency of a CPL emitter, dissymmetry factor (glum) is not enough. In the following we propose a new quantity, named CPL brightness (BCPL), which takes into account absorption extinction coefficient and quantum yield along with the glum factor. We calculated BCPL value for more than 180 compounds reported in the literature and we analyse data distribution for the main classes of CPL molecular emitters. This tool can be employed to put into context new CPL active compounds and to direct the choice of molecular systems for specific CPL applications.

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Section: Cpl Emittersmentioning

confidence: 99%

Quantifying the Overall Efficiency of Circularly Polarized Emitters

Arrico

Bari

Zinna

2020

Chemistry A European J

396

409

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“…Single azahelicenes, such as 3-(2-pyridyl)-4-aza[6]helicene ( H9 ) [82] and 3-(2-pyridyl)-4-aza[6]-helicene ( H10 ) [83], had the similar ϕ F values to those of H7 and H8 , but had the lower |g lum | values than those of H7 and H8 . According to the results of Hiroto and Shinokubo et al [84], the 1,4-diketones were converted to oxahelicenes ( H11 ), which exhibited strong fluorescence (66.0%) both in solution and solid state as well as chiroptical properties (1.2 × 10 −3 ). Tanaka et al [85] achieved the first enantioselective synthesis of a sila[7]helicene ( H12 ) through the double [2 + 2 + 2] cycloaddition of a biaryl-linked tetrayne with a silicon-linked bis (propargylic alcohol) as a key step.…”

Section: Progress On Experimental Researchesmentioning

confidence: 99%

Recent Theoretical and Experimental Progress in Circularly Polarized Luminescence of Small Organic Molecules

2018

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Small organic molecules (SOMs) with fascinating chiroptical properties have received much attention for their potential applications in photoelectric and biological devices. As an important research tool, circularly polarized luminescence (CPL) provides information about the chiral structures of these molecules in their excited state, and has been an active area of research. With the development of the commercially available CPL instrumentation, currently, more and more research groups have attempted to enhance the CPL parameters (i.e., quantum yield and dissymmetry factor) of the chiral SOMs from all aspects. This review summarizes the latest five years progresses in research on the experimental techniques and theoretical calculations of CPL emitted from SOMs, as well as forecasting its trend of development.

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“…The CPL spectra of 3c are shown in Figureà. The dissymmetric factor g (normalized difference in emission of right‐handed and left‐handed CPL) was determined to be 1.4 × 10 –3 at 543 nm, which is comparable to that of π‐extended [7]helicene‐like molecule VII (Figureà) (| g | 1.2 × 10 –3 at 550 nm) …”

Section: Resultsmentioning

confidence: 81%

Helicenes Fused with Hexafluorocyclopentene (HFCP): Synthesis, Structure, and Properties

et al. 2020

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Helicenes fused with hexafluorocyclopentene (HFCP) were synthesized by oxidative photocyclization of stilbene derivatives (the Mallory reaction). Of the newly‐obtained fluorinated helicenes, the [7]helicenes bearing one‐ or three‐HFCP units were structurally characterized by X‐ray crystallographic analysis. The attempted synthesis of [9]helicene fused with three HFCP units resulted in the unexpected formation of a novel double helicene consisting of [4]‐ and [6]‐helicenes sharing peripheral benzene rings. Optical properties and chiral resolutions of the newly obtained HFCP‐substituted helicenes are also described.

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Isolation of a 1,4-diketone intermediate in oxidative dimerization of 2-hydroxyanthracene and its conversion to oxahelicene

Cited by 49 publications

References 32 publications

Quantifying the Overall Efficiency of Circularly Polarized Emitters

Quantifying the Overall Efficiency of Circularly Polarized Emitters

Recent Theoretical and Experimental Progress in Circularly Polarized Luminescence of Small Organic Molecules

Helicenes Fused with Hexafluorocyclopentene (HFCP): Synthesis, Structure, and Properties

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