Improved Methods for the Synthesis of B10H14 and N-Heterocycle-Coordinated B9H13 (N-Het·B9H13) DOI
Ximeng Chen, Yiwen Ge,

Xing-Chao Yu

et al.

Inorganic Chemistry, Journal Year: 2024, Volume and Issue: 64(1), P. 268 - 274

Published: Dec. 26, 2024

Improved methods for the synthesis of B10H14 and a series N-heterocycle-coordinated B9H13 complexes (N-Het·B9H13) have been developed with readily obtained KB11H14 as starting material. Oxidation could provide in over 90% yield. Then, N-Het·B9H13 were prepared from as-synthesized through situ multistep reactions by reacting NaH, N-heterocycles, dilute hydrochloric acid. Among these complexes, 4-(triphenylvinyl)pyridine-coordinated (1k) exhibits significant aggregation-induced emission (AIE) effect THF/H2O mixed solution, 8-aminoisoquinoline-coordinated (2p) positive solvatochromism phenomenon. These improved new approaches to synthesizing potential applications luminescent materials.

Language: Английский

Unraveling aromaticity: the dual worlds of pyrazole, pyrazoline, and 3D carborane DOI Creative Commons
Zahra Noori, Miquel Solà, Clara Viñas

et al.

Beilstein Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: 21, P. 412 - 420

Published: Feb. 21, 2025

A new series of o -carborane-fused pyrazoles has been recently successfully synthesized. This fusion was expected to create a hybrid 3D/2D aromatic system, combining the 3D aromaticity -carborane with 2D pyrazole. However, while boron cage retains its character, pyrazole’s is lost. As result, rather than forming pyrazoles, synthesis yielded pyrazolines, which are non-aromatic. The limited overlap between π molecular orbitals (MOs) planar heterocycle and n + 1 MOs carborane prevents significant electronic delocalization two fused components. contrasts pyrazole benzene form indazole, where both rings maintain their aromaticity. Our findings demonstrate that peripheral σ-aromaticity π-aromaticity orthogonal, making true system unachievable. highly aromatic, generating negative NICS values (−25 −30 ppm). We have observed these high extend rings, leading incorrect estimations Therefore, relying solely on can be misleading, other computational indicators, along experimental or structural data, should used accurately assess

Language: Английский

Citations

1
Carborane in Polymers—Existent Stipulations and Technological Trademarks DOI
Ayesha Kausar

Polymer-Plastics Technology and Materials, Journal Year: 2025, Volume and Issue: unknown, P. 1 - 27

Published: Feb. 10, 2025

Language: Английский

Citations

0
Taming Inert B–H Bond with Low Energy Light: A Near-Infrared Light-Induced Approach to Facile Carborane Cluster-Amino Acid Coupling DOI

Sheng‐Wen Xu,

Hongjian Zhang,

Jibo Zong

et al.

Journal of the American Chemical Society, Journal Year: 2025, Volume and Issue: unknown

Published: April 1, 2025

The selective functionalization of inert B–H bonds in carborane clusters has been a formidable challenge. Recent advances have witnessed such reactions through photoredox methods utilizing ultraviolet or visible light irradiation. However, high-energy sources often suffer from poor energy efficiency, limited substrate scope, undesired side reactions, and low scalability. Here, we present the first successful bond under low-energy near-infrared (NIR) using carborane-based electron donor–acceptor complex. Both photophysical investigations theoretical modeling reveal facile single-electron transfer cage to electron-deficient photocatalyst, generating radical NIR follow-up pathway enables direct coupling carboranes with amino acids oligopeptides, yielding diverse array carborane-functionalized oligopeptides. Beyond expanding known chemical space boron cluster derivatives, further demonstrate that imaging targeting capabilities could serve as promising multifunctional carriers for neutron capture therapy. Thus, via not only provides straightforward practical strategy synthetic chemistry but also lays foundation development next-generation boron-containing biomolecules advanced functional materials.

Language: Английский

Citations

0
Synthesis of Carboranyl Alkyl Sulfide via Radical Thiol–Ene “Click” Reaction DOI
Dinghai Wang, Zhiyong He, Chang Liu

et al.

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

Published: April 7, 2025

Synthetic methods that feature mild reaction conditions and broad functional group tolerance are highly desired for the development of third-generation boron delivery agents, which significant neutron capture therapy (BNCT), a selective cancer treatment technique. Molecules containing carborane promising candidates as compounds BNCT. Herein, we report an efficient radical thiol-ene "click" involving carboranyl thiols unactivated alkenes under photoredox conditions. This affords moderate to excellent isolated yields. The current methodology allows incorporation carborane, valuable moiety with high content, into molecules outstanding this method makes it suitable late-stage introduction bioactive molecules. addition reactivity thiol was investigated by DFT calculations uncover impact 3D aromaticity on stabilization sulfur centered radical.

Language: Английский

Citations

0
Polyoxometalate-Supported Pd(II)-Catalyzed B(9)–H Nitration of o/m-Carboranes DOI
Yan Wang, Ye Li, Miaomiao Wang

et al.

ACS Catalysis, Journal Year: 2025, Volume and Issue: unknown, P. 7646 - 7652

Published: April 23, 2025

Language: Английский

Citations

0
A comparative study on nido- and closo-carborane supported zinc-salen catalysts for the ROCOP of epoxides and anhydrides DOI

Jin-Bian Xue,

Jiani Wang,

K Y Chen

et al.

Dalton Transactions, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

Nido -C 2 B 9 carborane anion supported Zn–salen complexes are superior to closo -carborane ones in ROCOP of epoxides and anhydrides.

Language: Английский

Citations

0
Borane-Mediated Polyhedral Expansion to Access Metal-Free Neutral and Cationic Derivatives of closo-Heptaboranes DOI
Penglong Wang, Rei Kinjo

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

Published: Oct. 2, 2024

Boranes with closed polyhedral structures feature peculiar bonding and structural characteristics, rendering them widely applicable in diverse research areas ranging from basic functionalization reactions to applications such as medicine, nanomaterials, molecular electronics, neutron capture therapy. Among the borane family, neutral cationic heptaborane B

Language: Английский

Citations

0
Improved Methods for the Synthesis of B10H14 and N-Heterocycle-Coordinated B9H13 (N-Het·B9H13) DOI
Ximeng Chen, Yiwen Ge,

Xing-Chao Yu

et al.

Inorganic Chemistry, Journal Year: 2024, Volume and Issue: 64(1), P. 268 - 274

Published: Dec. 26, 2024

Improved methods for the synthesis of B10H14 and a series N-heterocycle-coordinated B9H13 complexes (N-Het·B9H13) have been developed with readily obtained KB11H14 as starting material. Oxidation could provide in over 90% yield. Then, N-Het·B9H13 were prepared from as-synthesized through situ multistep reactions by reacting NaH, N-heterocycles, dilute hydrochloric acid. Among these complexes, 4-(triphenylvinyl)pyridine-coordinated (1k) exhibits significant aggregation-induced emission (AIE) effect THF/H2O mixed solution, 8-aminoisoquinoline-coordinated (2p) positive solvatochromism phenomenon. These improved new approaches to synthesizing potential applications luminescent materials.

Language: Английский

Citations

0