A Double Helicene with Quadruple Indole‐Fused Skeleton and Double NBN‐Type Cove‐Edged Structure DOI

Lingjuan Chen,

Jiaqi Dong,

Dehui Tan

et al.

Chinese Journal of Chemistry, Journal Year: 2024, Volume and Issue: 42(23), P. 3069 - 3074

Published: Aug. 1, 2024

Comprehensive Summary Construction of helicenes by inducing heteroatoms has regarded as an effective strategy to enhance the chiroptical properties. We report a facile synthesis multiple helicene based on four indoles with two electron‐rich NBN‐coved edges. The structure was confirmed single‐crystal X‐ray diffraction analysis, revealing twisted double [5]helicene motif saddle‐shaped skeleton. This showed strong green fluorescence good photoluminescence quantum yield. Both theoretical calculations and experimental investigation have been exploited probe impact NBN units aromaticity photophysical properties helicene.

Language: Английский

Controllable 1,4-Palladium Aryl to Aryl Migration in Fused Systems─Application to the Synthesis of Azaborole Multihelicenes DOI

Felix Full,

Albert Artigas,

Kevin Wiegand

et al.

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: 146(42), P. 29245 - 29254

Published: Oct. 11, 2024

Herein, we report the first 1,4-Pd aryl to migration/Miyaura borylation tandem reaction in fused systems. The Pd shift occurred bay region of dibenzo[

Language: Английский

Citations

3

Post-functionalization of end-capped twistacenes with pyrene units DOI
Sujuan Wang,

Tongtong Ye,

Jinchong Xiao

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(19), P. 5638 - 5669

Published: Jan. 1, 2024

This review covers recent advances in post-functionalization of twistacenes to realize polyacenes, chiral nanographenes and their semiconductor properties, emphasizing a promising future for constructing nanotubes.

Language: Английский

Citations

3

Recent Advances in the Development of Enantiopure BODIPYs and Some Related Enantiomeric Compounds DOI

Shaista Sultan,

Luis Crovetto, Ramón Rios

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 18, 2024

During the process of developing smart chiroptical luminophores, BODIPYs have emerged as candidates utmost importance. Here in we will discuss their synthesis.

Language: Английский

Citations

2

Narrowband Blue Circularly Polarized Luminescence Emitter based on BN‐Doped Benzo[6]helicene with Stimuli‐Responsive Properties DOI

Meiyan Liu,

Chenglong Li, Guanming Liao

et al.

Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: unknown

Published: Aug. 19, 2024

Abstract Boron‐doped helicenes, known for their unique electronic and photophysical properties, are of great interest numerous applications. This research introduces two new azabora[6]helicenes, H[6]BN1 H[6]BN2 , synthesized through an efficient method. These molecules have boron nitrogen atoms in opposing positions, enhancing distinctive attributes. Both helicenes show excellent emission with exhibiting narrowband blue fluorescence circularly polarized luminescence (CPL), achieving g lum values 4~5×10 −4 which is beneficial chiroptical The addition a donor group, 3, 6‐di‐tert‐butyl‐9H‐carbazole, improves luminescence, likely due to enhanced molecular orbital overlap electron delocalization. ′s needle‐like single crystals exhibit mechanochromism, changing luminescent color from yellow green under mechanical stress, promising stimulus‐responsive materials. In conclusion, this study presents novel class BN[6]helicenes superior properties. Their combination features mechanochromism makes them ideal advanced materials, expanding the potential helicene‐based compounds offering directions synthesis specific characteristics.

Language: Английский

Citations

1

Near‐IR Emissive B–N Lewis Pair‐Functionalized Anthracenes via Selective LUMO Extension in Conjugated Dimer and Polymer DOI Creative Commons

Jingyao Zuo,

Kanglei Liu,

Jaren Harrell

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(45)

Published: July 8, 2024

Abstract Acenes are attractive as building blocks for low gap organic materials with applications, example, in light emitting diodes, solar cells, bioimaging and diagnostics. Previously, we have shown that modification of dipyridylanthracene via B–N Lewis pair fusion (BDPA) strongly redshifts the emission, while facilitating self‐sensitized reactivity toward O 2 to reversibly generate corresponding endoperoxides. Herein, report on further expansion π‐system BDPA a vinyl‐substituted monomer, vinylene‐bridged dimer, polymer an average 20 chromophores. The extension π‐conjugation results largely reduced band gaps 1.8 eV dimer 1.7 polymer, latter giving rise NIR emission maximum at 731 nm appreciable quantum yield 7 %. Electrochemical computational studies reveal efficient delocalization lowest unoccupied molecular orbital (LUMO) along pyridyl‐anthracene‐pyridyl axis, which effective electronic communication between units, selectively lowers LUMO, ultimately narrows gap. Time‐resolved transient absorption (TA) measurements offer insights into pertinent photophysical processes. Extension also slows down formation endoperoxides, significantly accelerating thermal release singlet oxygen regenerate parent acenes.

Language: Английский

Citations

1

Novel Chiral Self-Assembled Nano-Fluorescence Materials with AIE Characteristics for Specific Enantioselective Recognition of L-Lysine DOI Open Access
Peng Wang, Rong Wang, Yue Sun

et al.

International Journal of Molecular Sciences, Journal Year: 2024, Volume and Issue: 25(19), P. 10666 - 10666

Published: Oct. 3, 2024

In this paper, two aggregation-induced emission (AIE) chiral fluorescent materials, S-1 and S-2, were synthesized. The materials are based on BINOL H8-BINOL backbones, respectively, large electron-absorbing groups attached to the backbones through Knoevenagel reaction. At same time, CD signals of these gradually weakened (fw increases) as they continue aggregate. However, S-2 underwent a flip-flop from negative positive signal at fw ≥ 90. And both also showed significant enantioselective recognition lysine, demonstrating their potential novel probes. Among them, fluorescence enhancement ratios (ef) for lysine 10.0 10.3, while different degrees blue shifts produced by ICT mechanism during process. addition, self-assembled morphology nanomaterials is different; comprises hollow-core vesicles that more likely aggregate form larger vesicles, whereas solid block structure. When L/D-lysine was added alone, distinctly compared S-2. With addition L-lysine, dispersed regularly spherical, with D-lysine, itself remained in aggregated vesicles. This suggests important fields optics, recognition, nanoscale self-assembly.

Language: Английский

Citations

1

Near‐IR Emissive B–N Lewis Pair‐Functionalized Anthracenes via Selective LUMO Extension in Conjugated Dimer and Polymer DOI Creative Commons

Jingyao Zuo,

Kanglei Liu,

Jaren Harrell

et al.

Angewandte Chemie, Journal Year: 2024, Volume and Issue: 136(45)

Published: July 8, 2024

Abstract Acenes are attractive as building blocks for low gap organic materials with applications, example, in light emitting diodes, solar cells, bioimaging and diagnostics. Previously, we have shown that modification of dipyridylanthracene via B–N Lewis pair fusion (BDPA) strongly redshifts the emission, while facilitating self‐sensitized reactivity toward O 2 to reversibly generate corresponding endoperoxides. Herein, report on further expansion π‐system BDPA a vinyl‐substituted monomer, vinylene‐bridged dimer, polymer an average 20 chromophores. The extension π‐conjugation results largely reduced band gaps 1.8 eV dimer 1.7 polymer, latter giving rise NIR emission maximum at 731 nm appreciable quantum yield 7 %. Electrochemical computational studies reveal efficient delocalization lowest unoccupied molecular orbital (LUMO) along pyridyl‐anthracene‐pyridyl axis, which effective electronic communication between units, selectively lowers LUMO, ultimately narrows gap. Time‐resolved transient absorption (TA) measurements offer insights into pertinent photophysical processes. Extension also slows down formation endoperoxides, significantly accelerating thermal release singlet oxygen regenerate parent acenes.

Language: Английский

Citations

0

A Double Helicene with Quadruple Indole‐Fused Skeleton and Double NBN‐Type Cove‐Edged Structure DOI

Lingjuan Chen,

Jiaqi Dong,

Dehui Tan

et al.

Chinese Journal of Chemistry, Journal Year: 2024, Volume and Issue: 42(23), P. 3069 - 3074

Published: Aug. 1, 2024

Comprehensive Summary Construction of helicenes by inducing heteroatoms has regarded as an effective strategy to enhance the chiroptical properties. We report a facile synthesis multiple helicene based on four indoles with two electron‐rich NBN‐coved edges. The structure was confirmed single‐crystal X‐ray diffraction analysis, revealing twisted double [5]helicene motif saddle‐shaped skeleton. This showed strong green fluorescence good photoluminescence quantum yield. Both theoretical calculations and experimental investigation have been exploited probe impact NBN units aromaticity photophysical properties helicene.

Language: Английский

Citations

0