Multicomponent Diversity-Oriented Access to Boronic-Acid-Derived Pyrrolide Salicyl-Hydrazone Fluorophores with Strong Solid-State Emission DOI
Changjiang Yu,

Guangyuan Di,

Qian Li

et al.

Inorganic Chemistry, Journal Year: 2024, Volume and Issue: 63(45), P. 21397 - 21409

Published: Oct. 31, 2024

Fluorescent molecular platforms are highly sought after for their applications in biology and optoelectronics but face challenges with solid-state emission quenching. To address this, bulky substituents or aggregation-induced luminogens to restrict intramolecular motion used enhance the brightness. Here, we have successfully engineered a novel class of boron complexed pyrrolide salicyl-hydrazone fluorophores named BPSHY. These dyes were synthesized through diversity-oriented condensation pyrrole salicylaldehyde derivatives combined various aromatic boronic acids. The resulting 3D structures, owing axially substituted aryl groups, impart excellent solubility variety solvents. Significantly, BPSHY exhibit strong absorption visible region remarkably large Stokes shifts. Crucially, they demonstrate intense aqueous solutions due effects. In solid-states, these achieve high quantum yields, reaching up 58%. Further expanding utility, developed two new probes: one incorporating morpholine another containing triphenylphosphine salt. Both them found specifically label subcellular organelles such as lysosomes mitochondria within live cells. Notably, probes exceptional staining efficacy two-photon fluorescence feature. This highlights considerable promise monitoring visualizing dynamic transformations organelles.

Language: Английский

Organocatalyzed Enantioselective C–N Bond-Forming SNAr Reactions for Synthesizing Stereogenic-at-Boron BODIPYs DOI Creative Commons
Yonggang Meng, Fang Wei, Z. Y. Pei

et al.

JACS Au, Journal Year: 2025, Volume and Issue: 5(4), P. 1965 - 1973

Published: April 2, 2025

The precise construction of boron stereogenic centers represents a significant, yet challenging frontier in asymmetric catalysis, garnering growing attention recent years. However, feasible catalysis has primarily been limited to transition-metal-catalyzed desymmetrization pro-chiral BODIPY molecules, while enantioselective synthesis via organocatalysis remains unexplored. Herein, we achieve an organocatalyzed C-N bond-forming SNAr reaction 3,5-dihalogen BODIPYs phase-transfer enabling the efficient broad range boron-stereogenic with excellent enantioselectivities (>40 examples, up 99% ee). significance and potential this catalytic approach are further underscored by versatile applications enantioenriched 3-amide synthesis, optical activity regulation, bioimaging, sensing, promoting development fluorophores.

Language: Английский

Citations

0
Phase-transfer-catalyst enabled enantioselective C–N coupling to access chiral boron-stereogenic BODIPYs DOI Creative Commons

Xueqing Zhang,

Xiaojuan Lv,

Luying Guo

et al.

Nature Communications, Journal Year: 2025, Volume and Issue: 16(1)

Published: March 19, 2025

Tetracoordinate boron-based fluorescent materials have shown extensively applications in chemistry, biology and science owing to their unique optoelectronic properties. However, constructing chiral boron-stereogenic fluorophores through practical universal strategies remains rare challenging. Herein, as a proof of concept, we report an enantioselective postfunctionalization boron dipyrromethene dyes (BODIPYs), acess BODIPYs moderate good yields with commendable enantioselectivity. Chiral attracted increasing attention not only distinctively photophysical properties circularly polarized luminescence (CPL) materials, but also diversely structural modification. In this·work, present phase-transfer-catalyst enabled C–N coupling reaction diverse nucleophiles. This method serves SNAr (nucleophilic aromatic substitution reaction) route achieve series amido/amino well demonstrates promising CD and·CPL·activities, excellent biocompatibility, high specificities, showing potential imaging agents. Constructing Here, the authors

Language: Английский

Citations

0
Asymmetric and Symmetric S-zig-zag-Fused BODIPYs: Synthesis and Photophysical and Oxidative Properties DOI
Ruihan Yang, Li Lu,

Shulin Gao

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: April 18, 2025

We present a new, straightforward, and versatile approach that utilizes regioselective brominated precursors to synthesize both asymmetric symmetric S-zig-zag-fused BODIPYs (s-TFB bis-TFB) in moderate yields (45% 40%, respectively). X-ray structure analyses reveal the planar rigidity of BODIPY skeleton is progressively enhanced with an increasing number thiopyran rings. The annulation S-heteroaromatic rings at zig-zag edge core results blue-shifted absorption emission spectra, bis-TFB exhibiting maxima 530 539 nm elevated LUMO energy levels. In contrast, oxidation s-TFB m-CPBA demonstrates significant site selectivity, affording four products, namely s-s-SFB, s-bis-SFB, bis-s-SFB, bis-bis-SFB, ranging from 22% 36%. These oxidated derivatives display large red-shifted spectra (e.g., 648 735 for s-bis-SFB), along more stable HOMO levels reduced HOMO-LUMO gaps. This cyclization/oxidation strategy enables precise tuning optoelectronic properties, opening new avenues dye design application.

Language: Английский

Citations

0
BODIPY: synthesis, modification, and applications in sensing and biomedicine DOI

Daniil Spector,

Daniil Abramchuk,

Vladislav Bykusov

et al.

Russian Chemical Reviews, Journal Year: 2024, Volume and Issue: 93(10), P. RCR5136 - RCR5136

Published: Oct. 1, 2024

BODIPY chromophores (4,4-difluoro-4-bora-3a,4a-diaza-s-indacene) are one of the most versatile fluorophores which commonly used in a variety scientific fields. The combination excellent photophysical properties with possibility easy chemical modification structure, and photostability determines application biomedicine, photocatalysis, analytical chemistry materials science. This review summarizes approaches to synthesis BODIPY, discussing both classical recently-published synthetic postfunctionalization approaches. An influence structure various methods on their potential applications science biosensorics also discussed.<br> bibliography includes 344 references.

Language: Английский

Citations

2
Recent Advances of Boron‐Containing Chiral Luminescent Materials† DOI Open Access

Jiaqi Di,

Shuran Han,

Pangkuan Chen

et al.

Chinese Journal of Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 25, 2024

Comprehensive Summary As a class of organic dyes, boron‐containing compounds play an important role in luminescent materials. They have attracted considerable attention due to their unique photophysical properties. Chiral systems wide range practical applications biological imaging, optoelectronic devices, information storage and 3D display. Boron‐containing chiral materials can not only effectively improve the properties CPL materials, but also bring system, which enables them be used as favorable emitting for expanded applications. Here, we review research progress by detailed discuss according different skeletons, such point chirality, 1,1’‐binaphthyl, [ n ]helicenes, [2,2]paracyclophane pillar[5]arenes. We believe that this is significance development Key Scientists The studies circularly polarized luminescence (CPL) based on small molecules advanced significantly. However, gained recent years. In 2019, Zhao's group prepared binaphthalene derivative modified with triarylborane, representing molecule material exhibit characteristics responsive both solvent fluoride ions. 2020, Chen's steric effects triarylborane triphenylamine prepare planar 2021, Wang's developed new B,N‐embedded double hetero[7]helicenes strong chiroptical responses UV‐visible region. same year, He's asymmetric reactions synthesize boron‐based point‐chirality high efficiency enantioselectivity. 2023, Ravat synthesized 1,4‐B,N‐embedded helicenes exhibiting narrow‐band fluorescence CPL. During period, Matthias Wagner et al obtained (BO) 2 ‐doped tetrathia[7]helicene via efficient four‐step synthesis, Zheng reported nearly pure green electroluminescent device (CP‐OLED). 2024, hetero‐[9]helicenes offering pathway towards significantly enhanced helicene‐based CPEL.

Language: Английский

Citations

2
Synthesis of BODIPY Oligomers Via Post‐Functionalization DOI
Mengna Zhao,

Hangqi Shen,

Y. L. Zhou

et al.

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(41)

Published: July 24, 2024

Abstract Synthesis of BODIPY oligomers has attracted increasing attention due to their intriguing properties and promising applications. Significant progress been made synthesize via post‐functionalization, either single‐bond linked or fully conjugated. This concept article highlights the recent developments oligomers, including synthetic routes, photophysical applications in areas NIR light absorbing dye, photodynamic therapy, bioimaging etc.

Language: Английский

Citations

1
Multicomponent Diversity-Oriented Access to Boronic-Acid-Derived Pyrrolide Salicyl-Hydrazone Fluorophores with Strong Solid-State Emission DOI
Changjiang Yu,

Guangyuan Di,

Qian Li

et al.

Inorganic Chemistry, Journal Year: 2024, Volume and Issue: 63(45), P. 21397 - 21409

Published: Oct. 31, 2024

Fluorescent molecular platforms are highly sought after for their applications in biology and optoelectronics but face challenges with solid-state emission quenching. To address this, bulky substituents or aggregation-induced luminogens to restrict intramolecular motion used enhance the brightness. Here, we have successfully engineered a novel class of boron complexed pyrrolide salicyl-hydrazone fluorophores named BPSHY. These dyes were synthesized through diversity-oriented condensation pyrrole salicylaldehyde derivatives combined various aromatic boronic acids. The resulting 3D structures, owing axially substituted aryl groups, impart excellent solubility variety solvents. Significantly, BPSHY exhibit strong absorption visible region remarkably large Stokes shifts. Crucially, they demonstrate intense aqueous solutions due effects. In solid-states, these achieve high quantum yields, reaching up 58%. Further expanding utility, developed two new probes: one incorporating morpholine another containing triphenylphosphine salt. Both them found specifically label subcellular organelles such as lysosomes mitochondria within live cells. Notably, probes exceptional staining efficacy two-photon fluorescence feature. This highlights considerable promise monitoring visualizing dynamic transformations organelles.

Language: Английский

Citations

1