Near‐IR Emissive B–N Lewis Pair‐Functionalized Anthracenes via Selective LUMO Extension in Conjugated Dimer and Polymer DOI Creative Commons

Jingyao Zuo,

Kanglei Liu,

Jaren Harrell

и другие.

Angewandte Chemie, Год журнала: 2024, Номер 136(45)

Опубликована: Июль 8, 2024

Abstract Acenes are attractive as building blocks for low gap organic materials with applications, example, in light emitting diodes, solar cells, bioimaging and diagnostics. Previously, we have shown that modification of dipyridylanthracene via B–N Lewis pair fusion (BDPA) strongly redshifts the emission, while facilitating self‐sensitized reactivity toward O 2 to reversibly generate corresponding endoperoxides. Herein, report on further expansion π‐system BDPA a vinyl‐substituted monomer, vinylene‐bridged dimer, polymer an average 20 chromophores. The extension π‐conjugation results largely reduced band gaps 1.8 eV dimer 1.7 polymer, latter giving rise NIR emission maximum at 731 nm appreciable quantum yield 7 %. Electrochemical computational studies reveal efficient delocalization lowest unoccupied molecular orbital (LUMO) along pyridyl‐anthracene‐pyridyl axis, which effective electronic communication between units, selectively lowers LUMO, ultimately narrows gap. Time‐resolved transient absorption (TA) measurements offer insights into pertinent photophysical processes. Extension also slows down formation endoperoxides, significantly accelerating thermal release singlet oxygen regenerate parent acenes.

Язык: Английский

Benzo-Extended Heli(aminoborane)s: Inner Rim BN-Doped Helical Molecular Carbons with Remarkable Chiroptical Properties DOI Creative Commons
Yang Yu, Chang Wang,

Faan-Fung Hung

и другие.

Journal of the American Chemical Society, Год журнала: 2024, Номер 146(32), С. 22600 - 22611

Опубликована: Авг. 5, 2024

Atomically precise synthesis of three-dimensional boron-nitrogen (BN)-based helical structures constitutes an undeveloped field with challenges in synthetic chemistry. Herein, we synthesized and comprehensively characterized a new class molecular carbons, named benzo-extended [n]heli(aminoborane)s (

Язык: Английский

Процитировано

9

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

и другие.

JACS Au, Год журнала: 2025, Номер 5(4), С. 1965 - 1973

Опубликована: Апрель 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.

Язык: Английский

Процитировано

1

Narrowband Blue Circularly Polarized Luminescence Emitter based on BN‐Doped Benzo[6]helicene with Stimuli‐Responsive Properties DOI

Meiyan Liu,

Chenglong Li, Guanming Liao

и другие.

Chemistry - A European Journal, Год журнала: 2024, Номер unknown

Опубликована: Авг. 19, 2024

Abstract Boron‐doped helicenes, known for their unique electronic and photophysical properties, are of great interest numerous applications. This research introduces two new azabora[6]helicenes, H[6]BN1 H[6]BN2 , synthesized through an efficient method. These molecules have boron nitrogen atoms in opposing positions, enhancing distinctive attributes. Both helicenes show excellent emission with exhibiting narrowband blue fluorescence circularly polarized luminescence (CPL), achieving g lum values 4~5×10 −4 which is beneficial chiroptical The addition a donor group, 3, 6‐di‐tert‐butyl‐9H‐carbazole, improves luminescence, likely due to enhanced molecular orbital overlap electron delocalization. ′s needle‐like single crystals exhibit mechanochromism, changing luminescent color from yellow green under mechanical stress, promising stimulus‐responsive materials. In conclusion, this study presents novel class BN[6]helicenes superior properties. Their combination features mechanochromism makes them ideal advanced materials, expanding the potential helicene‐based compounds offering directions synthesis specific characteristics.

Язык: Английский

Процитировано

3

Controllable 1,4-Palladium Aryl to Aryl Migration in Fused Systems─Application to the Synthesis of Azaborole Multihelicenes DOI

Felix Full,

Albert Artigas,

Kevin Wiegand

и другие.

Journal of the American Chemical Society, Год журнала: 2024, Номер 146(42), С. 29245 - 29254

Опубликована: Окт. 11, 2024

Herein, we report the first 1,4-Pd aryl to migration/Miyaura borylation tandem reaction in fused systems. The Pd shift occurred bay region of dibenzo[

Язык: Английский

Процитировано

3

Post-functionalization of end-capped twistacenes with pyrene units DOI
Sujuan Wang,

Tongtong Ye,

Jinchong Xiao

и другие.

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(19), С. 5638 - 5669

Опубликована: Янв. 1, 2024

This review covers recent advances in post-functionalization of twistacenes to realize polyacenes, chiral nanographenes and their semiconductor properties, emphasizing a promising future for constructing nanotubes.

Язык: Английский

Процитировано

3

Recent Advances in the Development of Enantiopure BODIPYs and Some Related Enantiomeric Compounds DOI

Shaista Sultan,

Luis Crovetto, Ramón Rios

и другие.

Chemical Communications, Год журнала: 2024, Номер unknown

Опубликована: Дек. 18, 2024

During the process of developing smart chiroptical luminophores, BODIPYs have emerged as candidates utmost importance. Here in we will discuss their synthesis.

Язык: Английский

Процитировано

3

Harnessing Aggregation‐Induced Emission‐Based Detection Toolbox for Diagnostics of Urogenital Tumors DOI Creative Commons
Wenzhe Chen,

Hantian Guan,

Yongfeng Lu

и другие.

Aggregate, Год журнала: 2025, Номер unknown

Опубликована: Фев. 13, 2025

ABSTRACT Urogenital system tumors include prostate cancer, bladder ovarian and other very common solid tumor diseases with high morbidity mortality. The unique physiological anatomical features of the urogenital render it particularly amenable to application tissue imaging techniques for diagnostic purposes. advancement aggregation‐induced emission (AIE) materials has addressed limitations associated conventional fluorescent that are prone aggregation‐caused quenching. This facilitated development innovative AIE characterized by enhanced photostability, an increased signal‐to‐noise ratio, improved quality. article reviews research progress biosensors in diagnosis tumors. It mainly involves biomarker vitro fluorescence such as uterine which based on biosensors. In addition, a comprehensive description biosensors’ synthesis strategies is provided. includes detailed elucidation platforms intracellular mechanisms basic principles AIE, accompanied presentation quantitative analysis cell results. limitations, challenges suggestions field summarized, prospect prospected. tumors, also provides catalyst exploring characteristics its wide disease diagnosis.

Язык: Английский

Процитировано

0

Brightening Up Circularly Polarized Luminescence of [6]Helicenes by Fusion with BN-Heterocycles DOI
Min Wang, Mengyuan Zhang, Cui‐Hua Zhao

и другие.

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Фев. 20, 2025

We here disclose synthesis and properties of a series BN-heterocycle-fused [6]helicenes. The fusion the BN-heterocycle is helpful to extend π-conjugation increase absorptivity fluorescence efficiency first excited state. Especially, double [6]helicene BiBN-BiHC shows outstanding circularly polarized luminescence performance with BCPL up 49.0 M–1 cm–1, owing its very high ΦF (0.87), large ε (5.47 × 104 cm–1), fairly good |glum| (2.06 10–3).

Язык: Английский

Процитировано

0

Recent development of azahelicenes showing circularly polarized luminescence DOI Creative Commons
Chihiro Maeda, Tadashi Ema

Chemical Communications, Год журнала: 2025, Номер unknown

Опубликована: Янв. 1, 2025

This feature article summarizes the recent developments of azahelicenes showing circularly polarized luminescence.

Язык: Английский

Процитировано

0

Axial and Helical Chirality in Multinuclear Group 13 Complexes: Pathways to Functional Optical Materials DOI Creative Commons
Toshikazu Ono, Yousuke Ooyama

Dalton Transactions, Год журнала: 2025, Номер unknown

Опубликована: Янв. 1, 2025

Multinuclear group 13 complexes adopting axial and helical chirality exhibit unique structural chiroptical properties. This work highlights recent advances in their design, synthesis, photophysical behaviors.

Язык: Английский

Процитировано

0