A logical construction of monomeric subunits armed with the carbonyl functionality allowing post-synthetic reactivity leads to the convergent formation of π-extended defected units activated with BBr. The kinetic or thermodynamic control entraps either the pyrido[2,3-]quinoline or the 4,7-phenanthroline motifs doped with boron(III), which deeply modulates the optical properties.
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http://dx.doi.org/10.1039/d2cc01801b | DOI Listing |
Org Lett
December 2024
Ningbo Key Laboratory of Biomedical Imaging Probe Materials and Technology, Laboratory of Advanced Theranostic Materials and Technology, Ningbo Institute of Materials Technology and Engineering, Chinese Academy of Sciences, Ningbo, Zhejiang 315201, China.
-directed 2-fold bromoboration reactions of diynes with BBr have been developed, allowing the access to novel internally BN-doped polycyclic aromatic hydrocarbons from readily available precursors under mild conditions. Computational investigations identified three potential reaction mechanisms, each involving either BBr or [BBr], with low activation barriers ( < 16 kcal/mol) for all pathways. The resulting brominated products can be further functionalized through various cross-coupling protocols, enabling the synthesis of highly luminescent emitters with quantum yield exceeding 90.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
January 2025
Shenzhen Key Laboratory of Nanozymes and Translational Cancer Research, Department of Otolaryngology, Shenzhen Institute of Translational Medicine, The First Affiliated Hospital of Shenzhen University, Shenzhen Second People's Hospital, Shenzhen, 518035, China.
Multiple resonance (MR) boron-nitrogen doped polycyclic aromatic hydrocarbons (BN-PAHs) have shown compelling thermally activated delayed fluorescence (TADF), surpassing those of their hydrocarbon analogues. However, the structural variety of π-extended BN-PAHs remains narrow. In this study, we synthesized three double helical BN-doped nanographenes (BN-NGs), 2 a-2 c, and three heptagon-embedded BN-NGs, 1 a-1 c, by π-extension of the MR core.
View Article and Find Full Text PDFChem Sci
February 2024
State Key Laboratory of Advanced Technology for Materials Synthesis and Processing, Center of Smart Materials and Devices, Wuhan University of Technology Wuhan 430070 China
Replacing the C[double bond, length as m-dash]C bond with an isoelectronic BN unit is an effective strategy to tune the optoelectronic properties of polycyclic aromatic hydrocarbons (PAHs). However, precise control of the BN orientations in large PAH systems is still a synthetic challenge. Herein, we demonstrate a facile approach for the synthesis of BN embedded perylene diimide (PDI) nanoribbons, and the polarization orientations of the BN unit were precisely regulated in the two PDI trimers.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
April 2024
Shenzhen Key Laboratory of New Information Display and Storage Materials, College of Materials Science and Engineering, Shenzhen University, Shenzhen, 518060, P. R. China.
1,4-BN-doped polycyclic aromatic hydrocarbons (PAHs) have emerged as very promising emitters in organic light-emitting diodes (OLEDs) due to their narrowband emission spectra that may find application in high-definition displays. While considerable research has focused on investigating the properties of these materials, less attention has been placed on their synthetic methodology. Here we developed an efficient synthetic method for 1,4-BN-doped PAHs, which enables sustainable production of narrowband organic emitting materials.
View Article and Find Full Text PDFOrg Lett
February 2024
Julius-Maximilians-Universität Würzburg, Institute of Inorganic Chemistry, Am Hubland, 97074 Würzburg, Germany.
Two unprecedented fluorescent nucleosides that feature BN-doped polycyclic aromatic hydrocarbons are presented. One of them, having a BN-modified phenanthrene moiety incorporated, shows blue fluorescence but suffers from poor stability under aqueous conditions. The other nucleoside comprises an internally BN-doped pyrene as the chromophore.
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