A Deep‐Red Emissive Sulfur‐Doped Double [7]Helicene Photosensitizer: Synthesis, Structure and Chiral Optical Properties DOI
Wenwen Yang, Ziwu Ren, Feng Jiao

et al.

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

Published: Aug. 8, 2024

Abstract Doping of polycyclic conjugated hydrocarbons (PCHs) with sulfur atoms is becoming more and important as a means creating unique functional materials. Recently, thiophene‐containing multiple helicenes have garnered enormous attention due to their intriguing electronic (chir)optical properties compared carbohelicenes. However, the efficient synthesis thiopyran‐containing underlying doping mechanisms are rather unexplored. Herein, structural analysis double [7]helicene 3 reported. X‐ray crystallographic reveals its dication C 2 ‐symmetric propeller‐shape structures compact interactions in solid state. exhibits deep‐red near‐infrared (NIR) fluorescence emission. Tunable aromaticity central benzene ring thiopyran rings found by chemical oxidation, which further confirmed nucleus‐independent shift (NICS), anisotropy induced current density (ACID) harmonic oscillator model (HOMA) analysis. Furthermore, chiral photosensitizing characters investigated. The excellent NIR fluorescence, circularly polarized luminescence (CPL) activities suggest that can be used an outstanding photosensitizer photodynamic therapy (PDT) bioimaging, especially paving way for future CPL‐PDT CPL‐bio‐probe applications.

Language: Английский

Boron-containing helicenes as new generation of chiral materials: opportunities and challenges of leaving the flatland DOI Creative Commons
Agnieszka Nowak‐Król,

Patrick T. Geppert,

Kenkera Rayappa Naveen

et al.

Chemical Science, Journal Year: 2024, Volume and Issue: 15(20), P. 7408 - 7440

Published: Jan. 1, 2024

Recent advances in synthesis have opened the way to a variety of boron helicenes. We highlight main achievements these chiral compounds and discuss their photophysical properties potential as functional materials.

Language: Английский

Citations

18
A highly fluorescent bora[6]helicene exhibiting circularly polarized light emission DOI Creative Commons

Matthias Schnitzlein,

Kazutaka Shoyama, Frank Würthner

et al.

Chemical Science, Journal Year: 2024, Volume and Issue: 15(8), P. 2984 - 2989

Published: Jan. 1, 2024

Heteroatom-doped helicenes have attracted great research interest due to their inherent chirality enabling fascinating new applications. Herein we present our successful synthesis of 19c-boratribenzo[

Language: Английский

Citations

13
Boron‐ and Oxygen‐Doped π‐Extended Helical Nanographene with Circularly Polarised Thermally Activated Delayed Fluorescence DOI
Geethu Venugopal, V. Ravi Kumar,

Ashok Badrinarayan Jadhav

et al.

Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: 30(19)

Published: Jan. 25, 2024

Abstract Helical nanographenes have garnered substantial attention owing to their finely adjustable optical and semiconducting properties. The strategic integration of both helicity heteroatoms into the nanographene structure, facilitated by a boron‐oxygen‐based multiple resonance (MR) thermally activated delayed fluorescence (TADF), elevates its photophysical chiroptical features. This signifies introduction an elegant category helical that combines (TADF) (CPL) In this direction, we report synthesis, optical, properties boron, oxygen‐doped Π‐extended nanographene. π‐extension induces distortion in DOBNA‐incorporated nanographene, endowing pair helicenes, ( P)‐ B2NG , M)‐ exhibiting circularly polarized luminescence with g lum −2.3×10 −3 +2.5×10 respectively. exhibited MR‐TADF lifetime below 5 μs, reasonably high quantum yield (50 %). Our molecular design enriches opens up new opportunities multidisciplinary fields.

Language: Английский

Citations

10
Benzo-Extended Heli(aminoborane)s: Inner Rim BN-Doped Helical Molecular Carbons with Remarkable Chiroptical Properties DOI Creative Commons
Yang Yu, Chang Wang,

Faan-Fung Hung

et al.

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: 146(32), P. 22600 - 22611

Published: Aug. 5, 2024

Atomically precise synthesis of three-dimensional boron-nitrogen (BN)-based helical structures constitutes an undeveloped field with challenges in synthetic chemistry. Herein, we synthesized and comprehensively characterized a new class molecular carbons, named benzo-extended [n]heli(aminoborane)s (

Language: Английский

Citations

8
Helically Chiral π‐Expanded Azocines Through Regioselective Beckmann Rearrangement and Their Charged States DOI Creative Commons

Jan Borstelmann,

Lars Schneider,

Frank Röminger

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(29)

Published: May 8, 2024

Abstract We report a synthetic approach to π‐expanded [6]helicenes incorporating tropone and azocine units in combination with 5‐membered ring, which exhibit intriguing structural, electronic, chiroptical properties. The regioselective Beckmann rearrangement allows the isolation of helical scaffolds containing 8‐membered lactam, azocine, amine units. As shown by X‐ray crystallographic analysis, incorporation or leads highly distorted [6]helicene moieties, distinct packing motifs solid state. compounds promising optoelectronic properties considerable photoluminescence quantum yields tunable emission wavelengths depending on relative position nitrogen center within polycyclic framework. Separation enantiomers chiral high‐performance liquid chromatography (HPLC) allowed characterization their circular dichroism (CD) circularly polarized luminescence (CPL) spectroscopy. feature manifold redox chemistry, allowing for corresponding radical anions cations as well dications dianions, near‐infrared (NIR) absorption bands extending beyond 3000 nm. Detailed theoretical studies provided insights into aromaticity evolution upon reduction oxidation, suggesting that steric strain prevents unit from undergoing aromatization, while indene moiety dominates observed chemistry.

Language: Английский

Citations

7
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

6
A Deep‐Red Emissive Sulfur‐Doped Double [7]Helicene Photosensitizer: Synthesis, Structure and Chiral Optical Properties DOI
Wenwen Yang, Ziwu Ren, Feng Jiao

et al.

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

Published: Aug. 8, 2024

Doping of polycyclic conjugated hydrocarbons (PCHs) with sulfur atoms is becoming more and important as a means creating unique functional materials. Recently, thiophene-containing multiple helicenes have garnered enormous attention due to their intriguing electronic (chir)optical properties compared carbohelicenes. However, the efficient synthesis thiopyran-containing underlying doping mechanisms are rather unexplored. Herein, structural analysis double [7]helicene 3 reported. X-ray crystallographic reveals its dication C

Language: Английский

Citations

5
Brightening Up Circularly Polarized Luminescence of [6]Helicenes by Fusion with BN-Heterocycles DOI
Min Wang, Mengyuan Zhang, Cui‐Hua Zhao

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 20, 2025

We here disclose synthesis and properties of a series BN-heterocycle-fused [6]helicenes. The fusion the BN-heterocycle is helpful to extend π-conjugation increase absorptivity fluorescence efficiency first excited state. Especially, double [6]helicene BiBN-BiHC shows outstanding circularly polarized luminescence performance with BCPL up 49.0 M–1 cm–1, owing its very high ΦF (0.87), large ε (5.47 × 104 cm–1), fairly good |glum| (2.06 10–3).

Language: Английский

Citations

0
Recent development of azahelicenes showing circularly polarized luminescence DOI Creative Commons
Chihiro Maeda, Tadashi Ema

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

Published: Jan. 1, 2025

This feature article summarizes the recent developments of azahelicenes showing circularly polarized luminescence.

Language: Английский

Citations

0
Double helicene possessing B-N dative bonds built on 1,4-dihydropyrrolo[3,2-b]pyrrole core DOI Creative Commons
Wojciech Petrykowski, Nicolas Vanthuyne, Carmelo Naim

et al.

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

Published: Jan. 1, 2025

Just four steps are required to transform 2-nitrobenzaldehyde into centrosymmetric, quadrupolar N,B-doped nanographenes possessing two nitrogen-boron dative bonds. A convergent fragment coupling strategy allowed rapid access key intermediates bearing...

Language: Английский

Citations

0