4.7 Article

Benzo[f]benzo[5,6]indolo[3,2-b] indole: a stable unsubstituted 4nπ-electron acene with an antiaromatic 1,4-diazapentalene core

Journal

CHEMICAL COMMUNICATIONS
Volume 50, Issue 25, Pages 3324-3327

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/c3cc49418g

Keywords

-

Funding

  1. Chinese Academy of Sciences
  2. National Science Foundation of China [21174157, 21103213, 91233106]

Ask authors/readers for more resources

A stable unsubstituted 4n pi-electron acene with an antiaromatic 1,4-diazapentalene core was prepared via an unprecedented mild oxidation. Further investigation showed that the stability of such acenes was dependent on the fusion patterns of the peripheryl benzene rings to the centre core.

Authors

I am an author on this paper
Click your name to claim this paper and add it to your profile.

Reviews

Primary Rating

4.7
Not enough ratings

Secondary Ratings

Novelty
-
Significance
-
Scientific rigor
-
Rate this paper

Recommended

Article Chemistry, Multidisciplinary

Monolithic polyimine vitrimer/graphene aerogel composites

Jinye Zhang, Shichang Luo, Yunlong Ma, Ruiyang Li, Yinghua Jin, Li Qiu, Wei Zhang

Summary: This study presents the fabrication method of cylindrical monolithic polyimine vitrimer/graphene composites with excellent mechanical, compressive, rehealable and recyclable, and piezoresistive properties. The composites exhibit outstanding durable compressibility, rapid recovery to the original size, high compressive strength, and high conductivity. The rehealing process achieves nearly 100% recovery of the compressive strength and electric conductivity under mild conditions, which is a desirable feature for electronic materials.

CHINESE CHEMICAL LETTERS (2023)

Article Chemistry, Physical

Cage-Confinement Induced Emission Enhancement

Rao Tao, Xin Zhao, Tianshu Zhao, Miaomiao Zhao, Ruiyang Li, Tianfu Yang, Lizhi Tang, Yinghua Jin, Wei Zhang, Li Qiu

Summary: In this proof-of-concept study, Imi-cage and Phos-cage organic molecular cages were designed to enhance emission through confinement effect. The cages exhibited higher fluorescence than free molecules in solid states, showcasing the potential for developing solid-state highly fluorescent materials. Additionally, Imi-cage showed promise for ultra-sensitive detection of explosives.

JOURNAL OF PHYSICAL CHEMISTRY LETTERS (2022)

Review Chemistry, Multidisciplinary

Design strategies of covalent organic framework-based electrodes for supercapacitor application

Rao Tao, Tianfu Yang, Yan Wang, Jingmin Zhang, Zhengyi Wu, Li Qiu

Summary: Supercapacitors (SCs) are considered a promising electrochemical energy storage (EES) device due to their high-power density, longer lifespan, faster charge and discharge capabilities, and environmental friendliness. Covalent organic frameworks (COFs), a newly emerging class of crystalline porous polymeric materials, have been found to have significant potential for application in EES devices due to their unique properties such as atomically adjustable structures, robust and tunable skeletons, well-defined and open channels, and high surface areas. This feature article aims to summarize the design strategies of COF-based electrode materials for SCs based on representative advances, as well as highlighting the current challenges and future perspectives of COFs for SC application.

CHEMICAL COMMUNICATIONS (2023)

Article Materials Science, Multidisciplinary

Alternating copolymers of thiophene-flanked thiazoloisoindigo and thiophene-flanked benzothiadiazole for high-performance ambipolar organic field-effect transistors

Bowen Li, Xiangyu Zou, Qiyi Li, Hongqian Sang, Youbing Mu, Jieyu Wang, Jian Pei, Chunming Yang, Liang Li, Xiaobo Wan

Summary: Research on conjugated polymers with planar backbone has led to the development of high charge carrier mobility in organic filed-effect transistors (OFETs). Two new ambipolar polymers with the same backbone but with/without hexyl sidechains were synthesized and their charge transport properties were compared. The results showed that the polymer with a moderately twisted backbone due to the sidechain exhibited higher crystallinity, smoother surface morphology, and better charge transport, suggesting the importance of considering the backbone geometry in the design of high-performance OFETs.

ORGANIC ELECTRONICS (2023)

Article Materials Science, Multidisciplinary

The Effects of Methoxylated Isoindigo on the Optical and Charge Transport Properties of the Corresponding Polymers

Zihan Xiong, Wei Wen, Yifei Zhu, Youbing Mu, Zhiyuan Zhao, Zhenggang Lan, Xiaobo Wan, Yunqi Liu

Summary: This study reports the synthesis of two methoxylated isoindigo molecules and investigates the charge transport behaviors of their copolymers with bisthiophene (2T) and bisthiazole (2Tz). The position of substitution has a drastic influence on the UV-vis absorption and electrochemical properties of both monomers and polymers. The presence of O center dot center dot center dot S conformation lock is confirmed by theoretical calculations and single crystal structure analysis, but the methoxy substitutions also change the aggregation behaviors of the corresponding polymers, which has a negative effect on charge transport. Among the four polymers, the one consisting of 5,5'-methoxylated isoindigo and 2T shows the best hole mobility of 1.9 x 10(-1) cm(2) V-1 s(-1).

MACROMOLECULAR MATERIALS AND ENGINEERING (2023)

Article Polymer Science

Preparation of robust diphenyl silicone elastomers with enhanced mechanical properties and thermal-aging resistances by using phosphazene as catalyst

Shiwei Duan, Zhedong Li, Yuetao Liu, Na Zhao, Zhibo Li

Summary: This study reports a facile method to prepare diphenyl silicone elastomer precursors with controlled structure by cyclic trimeric phosphazene base (CTPB) catalyzed ring -opening copolymerization. The resulting silicone elastomers exhibit excellent elasticity and thermal aging resistance, making them versatile for various applications.

POLYMER (2023)

Article Polymer Science

Stereoselective ring-opening polymerization of rac-lactide catalyzed by phenyl diphosphazene/urea binary catalytic system

Zhedong Li, Shiwei Duan, Na Zhao, Zhibo Li

Summary: In this study, two bulky phenyl diphosphazene bases, p-PDPB and m-PDPB, were synthesized and used in combination with ureas and squaramides as hydrogen-bond donors to mediate stereocontrolled ring opening polymerization (ROP) of lactide. The phenyl diphosphazene based/urea binary catalytic system successfully synthesized semicrystalline PLAs with narrow dispersity and high tacticity (P-m up to 0.84) in a well-controlled manner. Structural analysis confirmed the linear structure and high end-group fidelity of the resulting polymers, and MALDI-TOF MS analysis indicated the good controllability of the binary catalytic system with minimal transesterification.

JOURNAL OF POLYMER SCIENCE (2023)

Article Chemistry, Physical

Influence of Mode-Specific Excitation on the Nonadiabatic Dynamics of Methyl Nitrate (CH3ONO2)

Juanjuan Zhang, Jiawei Peng, Yifei Zhu, Deping Hu, Zhenggang Lan

Summary: The impact of mode-specific vibrational excitations on initial-preparation conditions in nonadiabatic dynamics of methyl nitrate was investigated. Exciting specific modes with a single quantum of energy resulted in slower population decay rates. This study provides insights into the key mechanisms of nonadiabatic dynamics control and demonstrates the potential for controlling nonadiabatic dynamics through mode-specific vibrational excitations.

JOURNAL OF PHYSICAL CHEMISTRY LETTERS (2023)

Article Materials Science, Multidisciplinary

Rehealable and Recyclable Aggregation-Induced Emission (AIE)-Active Luminescent Vitrimers

Ruiyang Li, Yunlong Ma, Tianfu Yang, Xiaoran Yang, Rao Tao, Yinghua Jin, Wei Zhang, Li Qiu

Summary: Incorporating an aggregation-induced emission (AIE) effect into polymers can create AIE-active polymers that have great potential in optoelectronics and sensing applications. This study successfully prepared a series of AIE-active polyimine vitrimers (TPE-PIs) by integrating AIE-active monomers into the polymer network. The TPE-PIs not only inherit the merits of PI vitrimers but also provide enhanced mechanical and luminescent properties compared to other AIE-active and AIE-inactive polymers. The possibility of significantly enhancing their photoluminescence intensity in an underwater environment makes them useful for underwater sensing and light-emitting applications.

ACS MATERIALS LETTERS (2023)

Article Chemistry, Physical

Simultaneously improving the efficiencies of photo- and thermal isomerization of an oxindole-based light-driven molecular rotary motor by a structural redesign

Jianzheng Ma, Di Zhao, Le Yu, Chenwei Jiang, Zhenggang Lan, Fuli Li

Summary: We theoretically designed a highly efficient light-driven molecular rotary motor using electronic structure calculations and nonadiabatic dynamics simulations, which showed excellent performance in both photo- and thermal isomerization processes. By modifying the structure of a synthesized compound, we proposed an oxindole-based light-driven molecular rotary motor with significant electronic push-pull character and weak steric hindrance. The newly designed motor displayed improved quantum yield and different motion behavior compared to the original motor, suggesting the feasibility of enhancing the efficiencies of photo- and thermal isomerization in molecular motors.

PHYSICAL CHEMISTRY CHEMICAL PHYSICS (2023)

Article Chemistry, Physical

Automated Exploration of Reaction Networks and Mechanisms Based on Metadynamics Nanoreactor Simulations

Yutai Zhang, Chao Xu, Zhenggang Lan

Summary: We developed an automated approach to construct complex reaction networks and explore reaction mechanisms by integrating various theoretical methods. This method combines nanoreactor-type molecular dynamics, metadynamics, semiempirical GFN2-xTB method, and hidden Markov model. It provides an efficient and accurate tool for the automated exploration of reaction networks.

JOURNAL OF CHEMICAL THEORY AND COMPUTATION (2023)

Article Chemistry, Physical

SbPh3-based organic molecular cage for size-controlled preparation and stabilization of palladium nanoparticles

Rao Tao, Tianfu Yang, Xian Li, Haofeng Gao, Shuangbin Liu, Yan Wang, Mingquan Yuan, Li Qiu

Summary: In this study, an organic molecular cage based on SbPh3 was synthesized and used to mediate the growth of palladium nanoparticles. The resulting ultrafine PdNPs showed good catalytic activity and stability in the reaction.

APPLIED SURFACE SCIENCE (2023)

Article Chemistry, Applied

Highly dispersed Pd nanoclusters supported on covalent triazine-based frameworks for highly efficient aryl nitro reduction and Ullmann coupling

Rao Tao, Yaqian Zheng, Yan Wang, Tianfu Yang, Li Qiu

Summary: A series of covalent triazine-based frameworks (CTFs) were prepared by ionothermal synthesis and rearrangement, and CTF-immobilized nano-Pd(0) catalysts with different particle size distributions were successfully prepared using suspension impregnation-in-situ reduction. Among them, the smallest and highly dispersed Pd nanoclusters showed excellent activity and recyclability. This study provides new insights for the preparation of high-performance metal nano-catalysts.

MICROPOROUS AND MESOPOROUS MATERIALS (2023)

Article Chemistry, Physical

The principal component analysis of the ring deformation in the nonadiabatic surface hopping dynamics

Yifei Zhu, Jiawei Peng, Xu Kang, Chao Xu, Zhenggang Lan

Summary: The analysis protocol proposed in this paper provides a powerful way to clarify both the major and minor active molecular motions of the ring distortion in nonadiabatic dynamics, using dimensionality reduction and clustering approaches. The representative system keto isocytosine is used to illustrate the protocol.

PHYSICAL CHEMISTRY CHEMICAL PHYSICS (2022)

Article Materials Science, Biomaterials

Mussel-inspired polymeric coatings with the antifouling efficacy controlled by topologies

Chenxi Xiong, Wenjuan Xiong, Youbing Mu, Danfeng Pei, Xiaobo Wan

Summary: Block copolymers with different topologies were synthesized to form a robust antifouling nanolayer, among which the 4-armed copolymer exhibited the best antifouling efficiency and superhydrophilic surface, along with excellent cytocompatibility.

JOURNAL OF MATERIALS CHEMISTRY B (2022)

Review Chemistry, Multidisciplinary

Trap suppression in ordered organic photovoltaic heterojunctions

Dan He, Yawen Li, Fuwen Zhao, Yuze Lin

Summary: High trap density in organic solar cells leads to localized charge carriers and reduced carrier lifetime, limiting device efficiency. This feature article summarizes the recent advances of trap suppression by material design and device engineering.

CHEMICAL COMMUNICATIONS (2024)

Review Chemistry, Multidisciplinary

Controversial mechanism of simultaneous photocatalysis and Fenton-based processes: additional effect or synergy?

Olivier Monfort, Arshitha Madhusudhan, Martin Motola

Summary: This article presents the advantages of coupling photocatalysis and Fenton-based processes for environmental remediation and discusses their synergy. It critically examines the simultaneous triggering of these two processes and provides insights into research approaches. The study aims to enhance understanding of this complex process and highlight the potential integration of new catalysts in current wastewater treatment technology.

CHEMICAL COMMUNICATIONS (2024)

Article Chemistry, Multidisciplinary

Polymerization of monomer aggregates for tailoring and patterning water wettability

Manideepa Dhar, Chittaranjan Mishra, Avijit Das, Uttam Manna

Summary: An approach of 'polymerization of monomers in its aggregated form' has been introduced to tailor the water wettability of fibrous and porous substrates, achieving hydrophobicity to superhydrophobicity transition, as well as patterned wettability. This facile chemical method provides a durable coating with adjustable and patterned wettability for various potential applications.

CHEMICAL COMMUNICATIONS (2024)

Article Chemistry, Multidisciplinary

Pd/Brønsted acid catalysed intramolecular N-allylation of indoles and pyrroles with alkynes for the synthesis of N-fused heterocycles

Saswat Ranjan Bhoi, Chhanda Debnath, Shikha Gandhi

Summary: In this article, a novel catalytic reaction using Pd(0) and Bronsted acid is reported for the synthesis of biologically important imidazolidinone-fused N-heterocycles through redox-neutral intramolecular N-allylation of indoles and pyrroles with alkynes. This atom-economical method is applicable to a wide range of substrates and eliminates the need for leaving groups or oxidizing agents commonly used in traditional allylation reactions.

CHEMICAL COMMUNICATIONS (2024)

Article Chemistry, Multidisciplinary

Rh(III)-catalyzed selective mono- and dual-functionalization/cyclization of 1-aryl-5-aminopyrazoles with iodonium ylides

Longkun Chen, Mingshuai Zhang, Meichen Liu, Zhuoyuan Liu, Yuetong Qiu, Zhilai Zhang, Fuchao Yu, Jiuzhong Huang

Summary: In this study, an efficient Rh(III)-catalyzed selective mono- and dual-C-H bond functionalization/cyclization with iodonium ylide as the sole coupling partner was demonstrated. Fused benzodiazepine skeletons were obtained in excellent yields, providing an improved approach to dual C-H unsymmetrical functionalization.

CHEMICAL COMMUNICATIONS (2024)

Article Chemistry, Multidisciplinary

Modified minimal-size fragments of heparan sulfate as inhibitors of endosulfatase-2 (Sulf-2)

Alice Kennett, Sven Epple, Gabriella van der Valk, Irene Georgiou, Evelyne Gout, Romain R. Vives, Angela J. Russell

Summary: This study presents the design and synthesis of sulfated disaccharide inhibitors based on IdoA(2S)-GlcNS(6S), which showed potent inhibition of Sulf-2. The results suggest that IdoA(2S)-GlcNS(6S) is the shortest fragment size required for effective inhibition of Sulfs, and a trisulfated disaccharide is identified as the minimal fragment size of heparan sulfate for effective endosulfatase inhibition.

CHEMICAL COMMUNICATIONS (2024)

Article Chemistry, Multidisciplinary

Reductive cyclodimerization of chalcones: exploring the self-adaptability of galvanostatic electrosynthesis

Mauro Garbini, Andrea Brunetti, Riccardo Pedrazzani, Magda Monari, Massimo Marcaccio, Giulio Bertuzzi, Marco Bandini

Summary: The self-adaptability of galvanostatic electrolysis was found to be helpful in a multistage chemo- and diastereoselective electrochemically promoted cyclodimerization of chalcones. Through a series of reductive events, densely functionalized cyclopentanes with five contiguous stereocenters were obtained (25 examples, yields up to 95%, dr values up to >20:1). Further experimental and electrochemical investigations indicated the crucial role of dynamic kinetic resolution of the aldol intermediate in the reaction mechanism.

CHEMICAL COMMUNICATIONS (2024)

Article Chemistry, Multidisciplinary

Rh(III)-catalyzed oxidative [4+2] annulation of 2-arylquinoxalines and 2-aryl-2H-indazoles with allyl alcohols

Dhananjay S. Nipate, Neha Meena, Prakash N. Swami, Krishnan Rangan, Anil Kumar

Summary: In this study, the synthesis of functionalized benzo[a]phenazines and indazolo[2,3-a]quinolines was achieved through Rh(III)-catalyzed oxidative annulation of 2-arylquinoxalines and 2-aryl-2H-indazoles with allyl alcohols. The method showed a wide substrate scope, excellent functional group tolerance, good to high yields of annulated products, and the capability for scaled-up synthesis. A tentative mechanism of the annulation reaction was proposed based on a preliminary mechanistic investigation.

CHEMICAL COMMUNICATIONS (2024)

Article Chemistry, Multidisciplinary

PbTeB4O9: a lead tellurium borate with unprecedented fundamental building block [B4O10] and large birefringence

Ruonan Zhang, Abudukadi Tudi, Xia Yang, Xuping Wang, Zhihua Yang, Shujuan Han, Shilie Pan

Summary: A new lead tellurium borate material with a unique fundamental building block [B4O10] was synthesized and found to exhibit high birefringence. The structure-property relationship was discussed using first-principles calculations.

CHEMICAL COMMUNICATIONS (2024)

Article Chemistry, Multidisciplinary

Wafer-scale synthesis of two-dimensional ultrathin films

Amresh Kumar Singh, Baishali Thakurta, Anupam Giri, Monalisa Pal

Summary: This study introduces three key concepts for the quick synthesis of large-scale high-quality 2D materials films and their utilization in device fabrication.

CHEMICAL COMMUNICATIONS (2024)

Article Chemistry, Multidisciplinary

Precise design of copolymer-conjugated nanocatalysts for active electron transfer

Reina Hagiwara, Shun Nishimura, Kosuke Okeyoshi

Summary: A copolymer-conjugated nanocatalytic system has been developed to improve electron transfer and enhance photoinduced H2 generation.

CHEMICAL COMMUNICATIONS (2024)