Heteroatom-boron-heteroatom-doped π-conjugated systems: structures, synthesis and photofunctional properties

Ma, Tinghao; Dong, Jiaqi; Yang, Deng-Tao

doi:10.1039/d3cc04302a

Chem. Commun.

2023

DOI: 10.1039/d3cc04302a

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Heteroatom-boron-heteroatom-doped π-conjugated systems: structures, synthesis and photofunctional properties

Tinghao Ma,

Jiaqi Dong,

Deng-Tao Yang

Abstract: The potency of heteroatom-doping in reshaping optoelectronic properties arises from the distinct electronegativity variations between heteroatoms and carbon atoms. By incorporating two heteroatoms with differing electronegativities (e.g., B=N), not only...

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2024

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Cited by 7 publications

References 42 publications

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Near‐Infrared‐Emitting Helically Twisted Conjugated Frameworks Consisting of Alternant Donor‐π‐Acceptor Units and Multiple Boron Atoms

Dong,

Chen,

Feng

et al. 2024

Angewandte Chemie

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A novel design strategy to construct bright and narrow near‐infrared (NIR) emission materials with suppressed shoulder peaks can significantly enhance their performance in various applications. Herein, we have successfully synthesized a series of helically twisted D‐π‐A conjugated systems bridged by boron atoms, achieving bright red to near‐infrared (NIR) emissions with notably narrow full‐width at half‐maximum (FWHM) values of 35 nm (0.08 eV) and photoluminescence quantum yield (PLQY) up to 80%. These compounds display redshifted emissions up to 753 nm in higher concentrations. Cis/trans configurational isomers of multi‐boron‐bridged molecule BN3 exhibit similar photophysical properties. The unique combination of boron‐induced coordination‐enhanced charge transfer (CE‐CT) and the helically twisted conjugated framework is pivotal in achieving the redshifted, narrowband emission. X‐ray crystallographic analysis of BN2 and BN3‐a reveals that the extension of boron‐bridged D‐π‐A skeletons significantly increases the distortion of the skeleton. Systematic theoretical calculations show how the boron CE‐CT mechanism, in conjunction with the helical twist, leads to the narrowing of emission bands while simultaneously red‐shifting them into the NIR region. This work could open new avenues for the development of advanced materials with tailored optical properties, particularly in the challenging and highly sought‐after NIR spectrum.

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Near‐Infrared‐Emitting Helically Twisted Conjugated Frameworks Consisting of Alternant Donor‐π‐Acceptor Units and Multiple Boron Atoms

Dong,

Chen,

Feng

et al. 2024

Angewandte Chemie

View full text Add to dashboard Cite

show abstract

Near‐Infrared‐Emitting Helically Twisted Conjugated Frameworks Consisting of Alternant Donor‐π‐Acceptor Units and Multiple Boron Atoms

Dong,

Chen,

Feng

et al. 2024

Angew Chem Int Ed

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

Chen,

Dong,

Tan

et al. 2024

Chin. J. Chem.

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

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Heteroatom-boron-heteroatom-doped π-conjugated systems: structures, synthesis and photofunctional properties

Abstract: The potency of heteroatom-doping in reshaping optoelectronic properties arises from the distinct electronegativity variations between heteroatoms and carbon atoms. By incorporating two heteroatoms with differing electronegativities (e.g., B=N), not only...

Cited by 7 publications

References 42 publications

Near‐Infrared‐Emitting Helically Twisted Conjugated Frameworks Consisting of Alternant Donor‐π‐Acceptor Units and Multiple Boron Atoms

Near‐Infrared‐Emitting Helically Twisted Conjugated Frameworks Consisting of Alternant Donor‐π‐Acceptor Units and Multiple Boron Atoms

Near‐Infrared‐Emitting Helically Twisted Conjugated Frameworks Consisting of Alternant Donor‐π‐Acceptor Units and Multiple Boron Atoms

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

Contact Info

Product

Resources

About

Heteroatom-boron-heteroatom-doped π-conjugated systems: structures, synthesis and photofunctional properties

Abstract: The potency of heteroatom-doping in reshaping optoelectronic properties arises from the distinct electronegativity variations between heteroatoms and carbon atoms. By incorporating two heteroatoms with differing electronegativities (e.g., B=N), not only...

Cited by 7 publications

References 42 publications

Near‐Infrared‐Emitting Helically Twisted Conjugated Frameworks Consisting of Alternant Donor‐π‐Acceptor Units and Multiple Boron Atoms

Near‐Infrared‐Emitting Helically Twisted Conjugated Frameworks Consisting of Alternant Donor‐π‐Acceptor Units and Multiple Boron Atoms

Near‐Infrared‐Emitting Helically Twisted Conjugated Frameworks Consisting of Alternant Donor‐π‐Acceptor Units and Multiple Boron Atoms

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

Contact Info

Product

Resources

About

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