A C2-symmetric triple [5]helicene based on N-annulated triperylene hexaimide for chiroptical electronics

Ma, Zetong; Winands, Thorsten; Liang, Ningning; Meng, Dong; Jiang, Wei; Doltsinis, Nikos L.; Wang, Zhaohui

doi:10.1007/s11426-019-9632-2

Cited by 45 publications

(35 citation statements)

References 34 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%

“…All the purely monomeric organic systems ( Hel‐1 – Hel‐46 ) present extinction coefficients in the range 10 4 –10 5 m −1 cm −1 and emission in the violet–green region (maxima between 406–560 nm) in most cases, while more rarely emission maxima fall in the red region (600–610 nm). Concerning [5]helicenes, [38, 40–43] the quantum yields are generally between 0.1 and 0.4. The g lum values are in the order of 10 −4 –10 −3 , thus translating into low B CPL values with a median value of 5 m −1 cm −1 and an average value of 4.9 m −1 cm −1 .…”

Section: Cpl Emittersmentioning

confidence: 99%

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Quantifying the Overall Efficiency of Circularly Polarized Emitters

Arrico

Bari

Zinna

2020

Chemistry A European J

390

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%

Section: Cpl Emittersmentioning

confidence: 99%

Quantifying the Overall Efficiency of Circularly Polarized Emitters

Arrico

Bari

Zinna

2020

Chemistry A European J

390

409

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“…Thec hemistry of making non-planar carbon-based aromatic systems [1] is attracting growing interest not only for their capability to modify and enhance the electronic and optical properties of their planar counterparts [2] but also to discover novel chiroptical properties of interest in avariety of applications. [3] Ap rerequisite for making them valuable as chiral materials in organic electronics [4] is to reach stereochemically rigid structures,t hus avoiding racemization processes.H owever,s trategies to reach rigid curved polycyclic aromatic hydrocarbons (PAHs) with enough stiffness and stability to study their chiroptical properties become exceptionally challenging. [5] To date,c reative synthetic methodologies have been used to isolate enantiopure helically twisted PA Hs.…”

Section: Introductionmentioning

confidence: 99%

Octagon‐Embedded Carbohelicene as a Chiral Motif for Circularly Polarized Luminescence Emission of Saddle‐Helix Nanographenes

et al. 2021

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We report a new family of hexa‐peri‐hexabenzocoronene (HBC)‐based helical nanographenes incorporating π‐extended carbo[5]helicenes bearing an octagonal carbocycle. This family represents a new kind of highly distorted saddle‐helix hybrid nanographenes. For the first time, the eight‐membered ring becomes a constituent of both a carbo[5]helicene and a HBC and thus, the negative curvature is responsible for twisting both units. This novel chiral motif, namely, oct‐[5]helicene results in the largest torsion angle recorded so far for a carbo[5]helicene (θ=79.5°), as it has been suggested by DFT‐calculations and confirmed by X‐ray crystallography. Consequently, the barriers of isomerization become exceptionally high for a [5]helicene unsubstituted in the fjord region since neither racemization nor decomposition were observed at 200 °C for 1 or 3 during 5 h. Therefore, racemic resolutions allowed subsequent chiroptical studies showing the ECD and CPL responses of this novel family of chiral nanographenes.

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“…Figure 13 summarizes the structural formula of single-molecule CPL-generating dyes [90,92,94,96,99,[103][104][105][106][107][108][109][110]. Most conventional organic materials that generate CPL are chiral fluorescent dyes that utilize the twisting and straining of molecules, [90] and therefore, require complicated chemical synthesis and purification processes.…”

Section: Circularly Polarized Luminescent Molecular Gelmentioning

confidence: 99%

Chiroptical Polymer Functionalized by Chiral Nanofibrillar Network

Ihara¹,

Takafuji²,

Kuwahara³

2021

Current Topics in Chirality - From Chemistry to Biology

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Chirality is one of the basic factors that influence a wide range of activities from chemical synthesis to tissue construction in life phenomena. Recently, researchers have attempted to use chirality as an optical signal. In animals, it is used to transmit information to insects and crustaceans, and it has also been confirmed that it promotes growth in plants. This chapter presents a new organic system that produces a chiral optical signal, that is, circularly polarized luminescence (CPL), which has been attracting attention in recent years. In particular, the chapter is focused on the generating CPL through chirality induction with the chiral self-assembling phenomenon and explaining its application as an optical film.

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A C2-symmetric triple [5]helicene based on N-annulated triperylene hexaimide for chiroptical electronics

Cited by 45 publications

References 34 publications

Quantifying the Overall Efficiency of Circularly Polarized Emitters

Quantifying the Overall Efficiency of Circularly Polarized Emitters

Octagon‐Embedded Carbohelicene as a Chiral Motif for Circularly Polarized Luminescence Emission of Saddle‐Helix Nanographenes

Chiroptical Polymer Functionalized by Chiral Nanofibrillar Network

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