1,1′-Binaphthol annulated perylene diimides: Aggregation-induced emission enhancement and chirality inversion

Zhang, Yang; Wang, Juejun; Chen, Hongming; Lin, Mei‐Jin

doi:10.1016/j.cclet.2021.11.069

Cited by 11 publications

(3 citation statements)

References 33 publications

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“…And thus, the signal attenuation and signal inversion in CD spectra were probably related to the aggregate structure, namely the intermolecular packing between chiral AIEgens during aggregates formation. [53][54] For SBTPE-Br andRBTPE-Br , the highly twisted structure had diminished the π-π stacking between luminogens, which was also supported by the reported crystal structure of SBTPE and RBTPE . By contrary, the extended conjugation (such as the phenyl rings, or cyano-stilbene units) within other three pairs of chiral AIEgens had provided planar conjugated surface for intermolecular π-π stacking.…”

Section: Full-color-tunable Cpl Via Donor-acceptor Engineeringsupporting

confidence: 67%

Full-color-tunable Chiral Aggregation-induced Emission Fluorophores with Tailored Propeller Chirality and their Circularly Polarized Luminescence

Li,

Liang,

et al. 2024

Preprint

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The regulation of emission color, emission efficiency and asymmetry factor is of great significance for the real applications of circularly polarized luminescent (CPL) materials. Herein, we develop a modular synthetic strategy toward full-color-tunable CPL materials based on chiral macrocyclic aggregation-induced emission (AIE) luminogens via delicate molecular engineering. Modular synthesis of chiral AIEgens with different acceptor moieties has afforded series of bright solid emitters with tunable emission colors. These chiral cyclic AIEgens have retained high solid state emission quantum yield and displayed CPL emission from blue to red as nano-aggregates, in liquid crystal matrix and polymer film. The strong acceptor units in the red-emitting chiral AIEgens RBTPE-2CN and SBTPE-2CN have rendered them twisted intramolecular charge transfer property and solvatochromic luminescence. And polymer matrix with different polarity further facilitates the tuning of CPL emission color from green to red emission. These results have paved a reliable approach toward constructing full-spectra solid-state CPL material.

show abstract

Section: Full-color-tunable Cpl Via Donor-acceptor Engineeringsupporting

confidence: 67%

Full-color-tunable Chiral Aggregation-induced Emission Fluorophores with Tailored Propeller Chirality and their Circularly Polarized Luminescence

Li,

Liang,

et al. 2024

Preprint

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“…(+)–Isokotanin A, isolated from the sclerotia of Aspergillus alliaceus, also includes the unit of axially chiral 2,2′-dihydroxy-1,1′-biaryl . Standing as the most representative structure with axial chirality, 2,2′-binaphthol (BINOL) and its derivatives, as well as NOBINs and BINAMs, have attracted particular interest due to their wide applications in asymmetric catalysis . From these basic axially chiral skeletons, diversified chiral organocatalysts and metal ligands could be easily accessible .…”

Section: Introductionmentioning

confidence: 99%

“… 10 Standing as the most representative structure with axial chirality, 2,2′-binaphthol (BINOL) and its derivatives, 11 as well as NOBINs and BINAMs, have attracted particular interest due to their wide applications in asymmetric catalysis. 12 From these basic axially chiral skeletons, diversified chiral organocatalysts and metal ligands could be easily accessible. 13 Up to today, many protocols have been developed to access the enantiopure form of axially chiral biaryls including chiral resolution, 14 asymmetric coupling reactions, 15 enzymatic hydrolysis/esterification, 16 and central-to-axial chirality transformations.…”

Section: Introductionmentioning

confidence: 99%

Deracemization of Atropisomeric Biaryls Enabled by Copper Catalysis

Zhang,

Wang,

Zhu

2024

JACS Au

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Atropisomeric biaryls have found crucial applications in versatile chiral catalysts as well as in ligands for transition metals. Herein, we have developed an efficient crystallizationinduced deracemization (CID) method to access chiral biaryls from their racemates with a chiral ammonium salt under copper catalysis including BINOL, NOBIN, and BINAM derivatives. After being significantly accelerated by its bidentate diamine ligand, the copper catalyst exhibits high efficiency and selectivity in racemizing biaryl skeletons, and the cocrystal complex would be enantioselectively formed together with chiral ammonium salt, which on acid-quenching would directly deliver chiral biaryl without further chromatographic purification. This CID process is easily scalable, and the chiral ammonium salt was nicely recoverable. Ligand effect studies showed that bulky alkyl substitution was an indispensable element to ensure efficient racemization, which probably proceeds via a radical-cation intermediate and further allows axial rotation by forming a delocalized radical.

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Full‐color‐tunable chiral aggregation‐induced emission fluorophores with tailored propeller chirality and their circularly polarized luminescence

Li,

Liang,

et al. 2024

Aggregate

View full text Add to dashboard Cite

The regulation of emission color, emission efficiency, and asymmetry factor is of great significance for the real applications of circularly polarized luminescent (CPL) materials. Herein, we develop a modular synthetic strategy toward full‐color‐tunable CPL materials based on chiral macrocyclic aggregation‐induced emission (AIE) luminogens via delicate molecular engineering. Modular synthesis of chiral AIEgens with different acceptor moieties has afforded a series of bright solid emitters with tunable emission colors. These chiral cyclic AIEgens have retained high solid‐state emission quantum yield and displayed CPL emission from blue to red as nano‐aggregates, in liquid crystal matrix and polymer film. The strong acceptor units in the red‐emitting chiral AIEgens RBTPE‐2CN and SBTPE‐2CN have rendered them twisted intramolecular charge transfer properties and solvatochromic luminescence. And polymer matrix with different polarity further facilitates the tuning of CPL emission color from green to red emission. These results have paved a reliable approach toward constructing full‐spectra solid‐state CPL material.

show abstract

1,1′-Binaphthol annulated perylene diimides: Aggregation-induced emission enhancement and chirality inversion

Cited by 11 publications

References 33 publications

Full-color-tunable Chiral Aggregation-induced Emission Fluorophores with Tailored Propeller Chirality and their Circularly Polarized Luminescence

Full-color-tunable Chiral Aggregation-induced Emission Fluorophores with Tailored Propeller Chirality and their Circularly Polarized Luminescence

Deracemization of Atropisomeric Biaryls Enabled by Copper Catalysis

Full‐color‐tunable chiral aggregation‐induced emission fluorophores with tailored propeller chirality and their circularly polarized luminescence

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