Direct C–H electrophilic borylation with (C6F5)2B–NTf2 to generate B–N dibenzo[a,h]pyrenes

Nguyen, Tony; Dutton, Jason L.; Chang, Chia Yun; Zhou, Wen; Piers, Warren E.

doi:10.1039/d4dt00469h

Dalton Trans.

2024

DOI: 10.1039/d4dt00469h

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Direct C–H electrophilic borylation with (C₆F₅)₂B–NTf₂ to generate B–N dibenzo[a,h]pyrenes

Tony Nguyen,

Jason L. Dutton,

Chia Yun Chang

et al.

Abstract: The borylation of aryl substituted pyridines is an effective way of preparing B-N doped conjugated organic frameworks. Trihaloborane Lewis acids are often employed for this protocol, and may require further...

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Organic Room Temperature Phosphorescence from BN‐Substituted Xanthene Derivatives

Watson,

Tao,

Siemiarczuk

et al. 2024

Angewandte Chemie

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Emissive organic materials are predominantly fluorescent and there is significant interest in realizing and understanding examples that defy this paradigm and exhibit phosphorescence under ambient conditions. Organic room temperature phosphorescence (ORTP) offers the long‐lived excited states and bathochromically‐shifted emission maxima of phosphorescence without the use of potentially toxic and expensive transition metals. Most ORTP materials rely on well‐studied structural motifs that include aryl carbonyls, sulfones, and heavy main group elements. We report the unexpected ORTP of a series of heavy atom‐free BN‐substituted xanthene derivatives. The creation of heteroatom‐rich scaffolds, combined with stabilizing C–H···F interactions in the solid‐state, resulted in oxygen‐tolerant heavy atom‐free organic phosphorescence without relying on the use of cryogenic temperatures, polymer matrices, or host‐guest interactions. The observation of ORTP in these simple systems sets a blueprint for the further development of heavy atom‐free organic phosphors.

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Organic Room Temperature Phosphorescence from BN‐Substituted Xanthene Derivatives

Watson,

Tao,

Siemiarczuk

et al. 2024

Angewandte Chemie

View full text Add to dashboard Cite

show abstract

Organic Room Temperature Phosphorescence from BN‐Substituted Xanthene Derivatives

Watson,

Tao,

Siemiarczuk

et al. 2024

Angew Chem Int Ed

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Direct C–H electrophilic borylation with (C₆F₅)₂B–NTf₂ to generate B–N dibenzo[a,h]pyrenes

Abstract: The borylation of aryl substituted pyridines is an effective way of preparing B-N doped conjugated organic frameworks. Trihaloborane Lewis acids are often employed for this protocol, and may require further...

Cited by 2 publications

References 51 publications

Organic Room Temperature Phosphorescence from BN‐Substituted Xanthene Derivatives

Organic Room Temperature Phosphorescence from BN‐Substituted Xanthene Derivatives

Organic Room Temperature Phosphorescence from BN‐Substituted Xanthene Derivatives

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