Synthesis and resolution of multi-chiral carbonyl-N embedded hetero[7]helicenes for efficient circularly polarized luminescence DOI
Yuxiang Wang, Qi Liao,

Yabin Feng

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(63), P. 8292 - 8295

Published: Jan. 1, 2024

Novel carbonyl-N embedded hetero[7]helicene diastereomers incorporating axially chiral binaphthyl were facilely synthesized and separated. The separated homochiral hetero[7]helicenes exhibit intense green photoluminescence circularly polarized luminescence (CPL) with dissymmetry factors (

Language: Английский

Axially Chiral Nonbenzenoid Nanographene with Second Harmonic Generation Property DOI

Liyuan Qin,

Jin Xie,

Botao Wu

et al.

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: 146(17), P. 12206 - 12214

Published: April 18, 2024

Chiral nanographenes (NGs) have garnered significant interest as optoelectronic materials in recent years. While helically chiral NGs been extensively studied, axially only witnessed limited examples, with no prior reports of nonbenzenoid NGs. Herein we report an nanographene featuring six pentagons and four heptagons. This compound, denoted 2, was efficiently synthesized via efficient Pd-catalyzed aryl silane homocoupling reaction. The presence two bulky 3,5-di-tert-butylphenyl groups around the axis connecting PAH (AHR) segments endows 2 atropisomeric chirality high racemization energy barrier, effectively preventing both R- S-enantiomers at room temperature. Optically pure R-2 S-2 were obtained by HPLC separation, they exhibit circular dichroism (CD) activity wavelengths up to 660 nm, one longest CD responses reported for Interestingly, racemic forms a homoconfiguration π-dimer crystal lattice, belonging I222 space group. Consequently, this unique structure renders crystals second harmonic generation (SHG) response, distinguishing it from all benzenoid Moreover, also SHG-CD properties.

Language: Английский

Citations

9
Ultra-Narrowband Circularly Polarized Luminescence from Multiple 1,4-Azaborine-Embedded Helical Nanographenes DOI
Fangyuan Zhang,

Vincenzo Brancaccio,

Fridolin Saal

et al.

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: 146(43), P. 29782 - 29791

Published: Oct. 22, 2024

In this manuscript we present a strategy to achieve ultranarrowband circularly polarized luminescence (CPL) from multiple 1,4-azaborine-embedded helical nanographenes. The impact of number and position boron nitrogen atoms in the rigid core molecule on optical properties─including absorption emission maxima, photoluminescence quantum yield, Stokes shift, excited singlet–triplet energy gap full width at half-maximum (fwhm) for CPL fluorescence─was investigated. molecules reported here exhibits fluorescence (fwhm 16–17.5 nm toluene) 18–19 toluene). To best our knowledge, is among narrowest any organic date. Quantum chemical calculations, including computed spectra involving vibronic contributions, provide valuable insights future molecular design aimed achieving narrowband CPL.

Language: Английский

Citations

5
Chiral helical scaffolds: Unlocking their potential in biomolecular interactions and biomedical applications DOI
Ghada Bouz, Jaroslav Žádný, Jan Storch

et al.

Biotechnology Advances, Journal Year: 2025, Volume and Issue: 79, P. 108513 - 108513

Published: Jan. 5, 2025

Language: Английский

Citations

0
Chiral nanographenes exhibiting circularly polarized luminescence DOI Creative Commons
V. Ravi Kumar,

J. Páez,

Sandra Míguez‐Lago

et al.

Chemical Society Reviews, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

Chiral nanographenes: molecular architecture, key constituents, and their circularly polarized luminescence.

Language: Английский

Citations

0
Enantiomer-enriched π-Extended Helicenes with a Perylene Core from Binaphthol: Axial-to-Helical Chirality Transfer with Stepwise Scholl Reaction Mechanism DOI Creative Commons

Zhi‐Ao Li,

Kelin Zhu, Nai‐Te Yao

et al.

Chemical Science, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

Axially chiral substrates were transformed into enantiomer-enriched π-extended helicenes via a chiral-transfer-based Scholl reaction, and enantiomers efficiently separated without labor-intensive high-performance liquid chromatography (HPLC).

Language: Английский

Citations

0
Double [5]carbohelicene: facile synthesis, chiroptical properties, isomerization study, and lasing application DOI
Peipei Liu,

Yantong Li,

Meng‐Xiang Wu

et al.

Science China Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 10, 2024

Language: Английский

Citations

2
Enantiomerically Pure Helical Bilayer Nanographenes: A Straightforward Chemical Approach DOI
Patricia Izquierdo‐García, Jesús M. Fernández‐García, Josefina Perles

et al.

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 6, 2024

The semiconductor properties of nanosized graphene fragments, known as molecular nanographenes, position them exceptional candidates for next-generation optoelectronics. In addition to their remarkable optical and electronic features, chiral nanographenes exhibit high dissymmetry factors in circular dichroism circularly polarized luminescence measurements. However, the synthesis enantiomerically pure remains a significant challenge. Typically, these materials are synthesized racemic form, followed by separation enantiomers using high-performance liquid chromatography (HPLC). While effective, this method often requires expensive instrumentation, extensive optimization conditions, typically yields analytical quantities desired samples. An alternative approach is enantioselective nanographenes; however, date, only two examples have been documented literature. work, we present straightforward chemical resolution helical bilayer nanographenes. This enables effective scalable preparation while avoiding need HPLC. incorporation BINOL core into polyarene precursor facilitates diastereomers through esterification with camphorsulfonyl chloride. Following standard chromatographic column, hydrolysis group nanographene precursors. subsequent graphitization, achieved Scholl reaction, occurs an enantiospecific manner concomitant formation furan ring heterohelicene moiety. absolute configurations final enantiomers, P-oxa[9]HBNG M-oxa[9]HBNG, determined X-ray diffraction. Additionally, electrochemical, photophysical, chiroptical thoroughly evaluated.

Language: Английский

Citations

2
W-Shaped π-Extended Double Undecabenzo[7]helicene DOI
Yun‐Jia Shen,

Li‐Jun Peng,

Li-Na Diao

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(35), P. 7279 - 7284

Published: July 18, 2024

A chiral W-shaped fully π-extended double [7]helicene (

Language: Английский

Citations

1
Topology-Directed Synthesis of Helical Phosphoniums with High Diradical Character and Polar-Dependent Electron Transfer DOI

Bo Yang,

Suqiong Yan,

Shirong Ban

et al.

Chemistry of Materials, Journal Year: 2024, Volume and Issue: unknown

Published: Aug. 14, 2024

Molecular topology synthesis of polycyclic aromatic hydrocarbons (PAHs) with diradical character takes root in intramolecular coupling breakthrough. Herein, we report selective Mn(III)/Cu(II)-mediated C–P and C–H bond cleavage to obtain robust donor-fused phosphoniums helical or planar geometries distinct cationic charges. The former structures incorporate a common phospha[5]helication acceptor different arylamine donors, the latter structure contains phospha[6]dication same donors. These unprecedented ionic salts hold distinguishing donor–acceptor (D–A) constructions, showing unique topology-dependent optoelectronic properties. folded radical ammoniums possess an extreme electron-deficient state through-space isolation high (y0 = 0.989). Moreover, tunable charge transfer (CT) locally excited (LE) transition components facilitate diverse hybridized local (HLCT) solvents, endowing highest emission band gap variation 0.78 eV (∼217 nm). fluorescence radiation could also be adjusted from blue near-infrared regions via tailoring polar-dependent states, which output additional circularly polarized luminescence compatible chiral menthol matrix elevated quantum efficiency undisturbed deep-red glow. It is worth mentioning that atomically precise Mn(III) halide has been unprecedentedly captured determined for activation.

Language: Английский

Citations

1
Double [7]Helicenes with Chiroptical Amplification DOI
Dahui Zhao,

Qiyuan Wan

Synfacts, Journal Year: 2024, Volume and Issue: 20(06), P. 0586 - 0586

Published: May 14, 2024

Key words helical nanographenes - circularly polarized luminescence chiropitical amplification double helicenes

Language: Английский

Citations

0