Nonplanar Nanographene: A Hydrocarbon Hole‐Transporting Material That Competes with Triarylamines DOI Open Access

Yuta Morinaka,

Hideto Ito, Kazuhiro J. Fujimoto

et al.

Angewandte Chemie, Journal Year: 2024, Volume and Issue: 136(44)

Published: Aug. 13, 2024

Abstract Hole‐transporting materials (HTMs) are essential for optoelectronic devices, such as organic light‐emitting diodes (OLEDs), dye‐sensitized solar cells, and perovskite cells. Triarylamines have been employed HTMs since they were introduced in 1987. However, heteroatoms or side chains embedded the core skeleton of triarylamines can cause thermal chemical stability problems. Herein, we report that hexabenzo[ a , c fg j l op ]tetracene (HBT), small nonplanar nanographene, functions hydrocarbon HTM with hole transport properties match those triarylamine‐based HTMs. X‐ray structural analysis theoretical calculations revealed effective multidirectional orbital interactions transfer integrals HBT. In‐depth experimental analyses nonplanarity‐inducing annulative π‐extension achieve not only stable amorphous state bulk films, but also higher increase highest occupied molecular level than conventional linear cyclic π‐extension. Furthermore, an in‐house manufactured HBT‐based OLED exhibited excellent performance, featuring superior curves current density–voltage, external quantum efficiency–luminance, lifetime compared to representative OLEDs. A notable improvement device was observed OLED, highlighting advantages HTM. This study demonstrates immense potential nanographenes applications.

Language: Английский

Mechanochemistry enabling highly efficient Birch reduction using sodium lumps and d-(+)-glucose DOI Creative Commons

Keisuke Kondo,

Koji Kubota, Hajime Ito

et al.

Chemical Science, Journal Year: 2024, Volume and Issue: 15(12), P. 4452 - 4457

Published: Jan. 1, 2024

In this study, a mechanochemical protocol for highly efficient and ammonia-free sodium-based Birch reduction was developed, leveraging the use of cheap easy-to-handle sodium lumps d -(+)-glucose as proton source.

Language: Английский

Citations

14

Synthesis of naphthalene derivatives via nitrogen-to-carbon transmutation of isoquinolines DOI Creative Commons

Tongtong Zhu,

Xiang Cui, Wenjun Ma

et al.

Science Advances, Journal Year: 2025, Volume and Issue: 11(5)

Published: Jan. 29, 2025

Heteroarene skeletal editing is gaining popularity in synthetic chemistry. Transmuting single atoms generates molecules that have distinctly varied properties, thereby fostering potent molecular exchanges can be extensively used to synthesize functional molecules. Herein, we present a convenient protocol for nitrogen-carbon single-atom transmutations isoquinolines, which inspired by the Wittig reaction and enables easy access substituted naphthalene derivatives. The uses an inexpensive commercially available phosphonium ylide as carbon source furnish wide range of naphthalenes. key success this transformation formation triene intermediate through ring opening, undergoes 6π-electrocyclization elimination processes afford product. Furthermore, strategy facile synthesis 13 C-labeled naphthalenes using CH 3 PPh I commercial C facilitates modifying directing group C─H functionalization.

Language: Английский

Citations

1

Intramolecular direct arylation through mechanochemistry: efficient synthesis of corannulene-based peri-annulated curved nanographenes DOI
Zhongbo Zhang, Mihaiela C. Stuparu

Science China Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 6, 2025

Language: Английский

Citations

1

Synthesis without solvent: consequences for mechanochemical reactivity DOI Creative Commons
Lauren E. Wenger, Timothy P. Hanusa

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(96), P. 14210 - 14222

Published: Jan. 1, 2023

Solution-based reactions are a staple of synthetic chemistry—but what happens mechanochemically, when there is no solvent?

Language: Английский

Citations

21

Mechanochemical Birch Reduction with Low Reactive Alkaline Earth Metals DOI
Jagadeesh Varma Nallaparaju,

Riin Satsi,

Danylo Merzhyievskyi

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(20)

Published: March 4, 2024

Abstract Birch reduction and similar dissolved metal‐type transformations hold significant importance in the organic synthesis toolbox. Historically, field has been dominated by alkali metal reductants. In this study, we report that largely neglected, low‐reactive alkaline earth metals can become powerful affordable reductants when used a ball mill under essentially solvent‐free conditions, presence of ethylenediamine THF as liquid additives. Calcium reduce both electron‐deficient electron‐rich arenes, with yields products to those obtained lithium metal. Magnesium reveals enhanced reducing power, enabling benzoic acids while keeping aromatic moieties intact allows for chemoselective transformations. The developed mechanochemical approach uses readily available safer‐to‐handle metals, operates air ambient temperature be gram‐scale preparations. Finally, demonstrate conditions other reductive transformations, including amination, deoxygenation, dehalogenation, alkene alkyne reductions.

Language: Английский

Citations

8

Mechanochemical activation of metallic lithium for the generation and application of organolithium compounds in air DOI Creative Commons

Keisuke Kondo,

Koji Kubota, Hajime Ito

et al.

Nature Synthesis, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 21, 2025

Language: Английский

Citations

0

Applications DOI
Davor Margetić

Elsevier eBooks, Journal Year: 2025, Volume and Issue: unknown, P. 83 - 177

Published: Jan. 1, 2025

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

Solution is not the only solution: nanographenes by mechanochemistry DOI
Mihaiela C. Stuparu

Trends in Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: April 1, 2025

Language: Английский

Citations

0

Rh-catalyzed mechanochemical transfer hydrogenation for the synthesis of periphery-hydrogenated polycyclic aromatic compounds DOI Creative Commons
Yoshifumi Toyama,

Takumu Nakamura,

Yoshimine Horikawa

et al.

Chemical Science, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

Hydrogenated nanographene has attracted attention as a new class of nanocarbon material owing to its potential applications in various research fields.

Language: Английский

Citations

0