Non‐Covalent Self‐Assembly Behaviors Based on Racemic Binaphthol Scaffolds DOI
Zhi‐Qiang Feng, Tingting Sun,

Xincai Luo

et al.

Chemistry - An Asian Journal, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 10, 2024

Understanding the fundamental mechanisms involved in construction and organization of multi-scale structures is crucial for design manufacture complex functional systems with long-range molecular arrangements. In this paper, a series compounds have been synthesized using racemic binaphthols as skeleton Suzuki coupling reaction derivatization at 6,6' positions, which resulted various bearing different groups. Control over self-assembly these binaphthol derivatives was successfully achieved by adjusting types positions substituents parent compound, revealed key factors influencing non-covalent interactions process. For example, single-crystal resulting indicated that assembly such single helix double based on non-traditional hydrogen bond motifs could be obtained, fascinating ladders catenane discovered.

Language: Английский

Dithio-Fused Boron Dipyrromethenes: Synthesis and Impact of S-Heteroaromatic Annulation Mode DOI
Jie Li, Ning Xue,

Shulin Gao

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(26), P. 5472 - 5477

Published: June 24, 2024

Three dithio-fused boron dipyrromethenes (BODIPYs), DTFB-1, DTFB-2, and DTFB-3, in which symmetrically S-heteroaromatic ring units fused at [a], zigzag, [b] bonds of the parent BODIPY core, respectively, were prepared from facile efficient post-functionalization tetra-halogenated BODIPYs through Pd-catalyzed cyclization. Dithio-fusion various positions effectively tunes their photophysical properties single-crystal structural packing arrangements. The single-crystalline microribbons DTFB-2 exhibit commendable hole mobilities air, reaching up to 0.03 cm2 V–1 s–1.

Language: Английский

Citations

11
Synthesis and characterizations of highly luminescent 5-isopropoxybenzo[rst]pentaphene DOI Creative Commons
Islam S. Marae, Jingyun Tan, Rengo Yoshioka

et al.

Beilstein Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: 21, P. 270 - 276

Published: Feb. 4, 2025

A benzo[ rst ]pentaphene (BPP) substituted by an isopropoxy group (BPP-OiPr) was synthesized in a facile manner. Its photophysical properties were investigated UV–vis absorption and fluorescence spectroscopy compassion to pristine BPP its oxidation product, ]pentaphene-5,8-dione (BPP-dione). BPP-OiPr exhibited significantly enhanced photoluminescence quantum yield (PLQY), reaching 73% comparison (13%). BPP-dione, when compared the parent BPP, also displayed improved emission from first excited singlet (S 1 ) state with PLQY of 62% intramolecular charge-transfer character. The rod-like nano- microcrystals as well longer wires these BPPs revealed scanning electron microscopy. intriguing optical derivatives may lead their application fluorophores.

Language: Английский

Citations

0
Intramolecular and intermolecular benzannulation of arylethanone derivatives enabled by visible light-induced catalytic generation of tether-tunable distonic radical anions DOI

Zhiyou Yu,

Ziye Zhan,

Kang Fu

et al.

Organic Chemistry Frontiers, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

A novel method enables inter-/intramolecular benzannulation to synthesize PAHs have been disclosed. Experimental and DFT data confirm the TDRA's role in HAA step of enolized 1,3-dicarbonyls via asynchronous PCET.

Language: Английский

Citations

0
Pyrene‐Based Blue Aggregation‐Induced Emission Luminogens: The Synergistic Effect of Through‐Space Conjugation for High Exciton Utilization Efficiency and Narrow‐Band and Blue OLEDs DOI
Wei Liu, Siwei Zhang, Tao Jiang

et al.

Advanced Optical Materials, Journal Year: 2025, Volume and Issue: unknown

Published: April 26, 2025

Abstract Achieving outstanding narrow‐band emission and improving the triplet exciton utilization efficiency is crucial for high organic light‐emitting diodes (OLEDs) electroluminescence (EL) efficiency. Herein, novel 1,3‐asymmetrical substituted pyrene‐based blue “hot exciton” materials with aggregation‐induced (AIE) characteristics are synthesized, utilizing pyrene ring's staggered energy levels high‐performance OLEDs. The triphenylamine‐decorated emitters exhibited narrow full width at half maxima (FWHM) < 60 nm, while tetraphenylethylene‐decorated compounds displayed a higher fluorescence quantum yield but broader FWHM in film state. These AIE luminogens (AIEgens) show good EL (>35.6%) nondoped OLED devices. Meanwhile, both pyrenes further utilized as an emitter layer thermally activated delayed (TADF)‐sensitized OLEDs great performance. Moreover, TPE‐decorated TPE‐ m 2Ph demonstrated maximum brightness, current efficiency, power external of 35230 cd −2 , 42 A −1 48 lm W 14.9%, respectively.

Language: Английский

Citations

0
Oxa-phenalene [b]-fused BODIPY Dyes: Synthesis, Structures, and Photophysical Properties DOI
Hao Guan, Ruihan Yang,

Limin He

et al.

Tetrahedron, Journal Year: 2025, Volume and Issue: unknown, P. 134728 - 134728

Published: May 1, 2025

Language: Английский

Citations

0
Palladium-Catalyzed Annulation Reaction of Bay-Diiodinated Arenes with o-Chloroaromatic Carboxylic Acids to Access Polycyclic Aromatic Compounds DOI
Li Song, C Cui, Na Huang

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(21), P. 15665 - 15677

Published: Oct. 13, 2024

A palladium-catalyzed annulation reaction of bay-diiodinated arenes with o-chloroaromatic carboxylic acids was established. This approach enables the synthesis a variety polycyclic aromatic compounds, especially polyalkoxy-substituted frequently found in discotic liquid-crystalline materials. The investigations indicate that product 2,3,8,9,12,13-hexakis(hexyloxy)-5-azadibenzo[fg,op]tetracene demonstrates favorable room-temperature properties.

Language: Английский

Citations

1
Facile Access to Phosphorus Ylide‐fused Heteroarenes Possessing Tunable Optoelectronic Properties and High Nonlinear Optical Performances DOI
Kaihua Zhang, Xiaofeng Wang, Zhiruo Zhou

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 18, 2024

We report here a novel family of ylidic P-heteroarenes (P1-P6), structurally featuring unique phosphonium cyclopentadienylide (P-Cp)-fused π-skeletons and synthetically prepared via an unexpected one-pot [2+3]/[3+3] phospha-annulation reaction. While the facile modular synthesis allows fine-tuning their optical absorptions redox properties, single-crystallographic theoretical analysis these further reveal that fusion P-Cp moiety leads to substantial intramolecular charge-separated features with high character values up 84 %. Benefitted from such dipolar structures, not only stepwise electrophilic substitution reaction for structural π-expansions, but also exhibit excellent nonlinear (NLO) responses limiting (OL) performances comparable or exceed those C

Language: Английский

Citations

1
Direct Synthesis of K-Region Functionalized Polycyclic Aromatic Hydrocarbons via Twofold Intramolecular C–H/C–H Arylation DOI
Hao Li,

Dandan Lu,

Bo Qian

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 11, 2024

Functionalized polycyclic aromatic hydrocarbons (PAHs) are essential building blocks for the bottom-up fabrication of structurally uniform nanocarbons. Herein we report a simple and efficient synthetic method toward K-region hydroxy-functionalized PAHs via TEMPO-mediated twofold intramolecular C-H/C-H arylations 1-biphenyl-2-yl-2-aryl-ethanone derivatives. This achieves high yields selectivity, synthesizing variety PAH frameworks, including pyrenes, chrysenes, benzo[

Language: Английский

Citations

1
Facile Access to Phosphorus Ylide‐fused Heteroarenes Possessing Tunable Optoelectronic Properties and High Nonlinear Optical Performances DOI Open Access
Kaihua Zhang, Xiaofeng Wang, Zhiruo Zhou

et al.

Angewandte Chemie, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 18, 2024

Abstract We report here a novel family of ylidic P‐heteroarenes ( P1 – P6 ), structurally featuring unique phosphonium cyclopentadienylide (P−Cp)‐fused π‐skeletons and synthetically prepared via an unexpected one‐pot [2+3]/[3+3] phospha‐annulation reaction. While the facile modular synthesis allows fine‐tuning their optical absorptions redox properties, single‐crystallographic theoretical analysis these further reveal that fusion P−Cp moiety leads to substantial intramolecular charge‐separated features with high character values up 84 %. Benefitted from such dipolar structures, not only stepwise electrophilic substitution reaction for structural π‐expansions, but also exhibit excellent nonlinear (NLO) responses limiting (OL) performances comparable or exceed those C 60 . As model compound, persistent radical‐anion salt P5a was through chemical reduction, thus offering valuable insights into electronic structures reduced P‐ylidic species. Our work established highly efficient synthetic method toward new P‐heteroarenes, provide fundamental understanding fused‐ring P‐heterocycles promising NLO/OL applications.

Language: Английский

Citations

0
Umpolung of 4,4-disubstituted 2-hydroxycyclohexa-2,5-dienones for the regiodivergent synthesis of disubstituted catechols DOI

Ryunosuke Akazawa,

Ahmed A. B. Mohamed, Kenzo Yahata

et al.

Bulletin of the Chemical Society of Japan, Journal Year: 2024, Volume and Issue: 97(11)

Published: Oct. 24, 2024

Abstract The umpolung of 4,4-disubstituted 2-hydroxycyclohexa-2,5-dienones 1 with PhI(OCOCF3)2 achieved the migration into more electron-rich C3 position, providing exclusively 3,4-disubstituted catechols 3. Acid-induced rearrangement produced 4,5-disubstituted 2. These two reactions enabled highly selective production regioisomers disubstituted catechols, especially biaryls containing catechol moieties, from common intermediates 1.

Language: Английский

Citations

0