Review
Chemistry, Applied
Maedeh Bagheri, Mohammadsadra Mirzaee, Sayedarmin Hosseini, Parisa Gholamzadeh
Summary: This article summarizes the history, development, and future of imidazole dimers, as well as introduces some heterocyclic structures derived from these compounds. Imidazole dimers have significant application prospects in switchable photochromic dyes.
Article
Chemistry, Multidisciplinary
Yuanhao Li, Fan Gu, Bingbing Ding, Lei Zou, Xiang Ma
Summary: Two polymers containing hexaarylbiimidazole are designed with dual emission of both fluorescence and phosphorescence, showing sensitive photochromic responses from faint yellow to brown upon exposure to ultraviolet light. This study enriches pure organic luminescent systems and provides new ideas for functional RTP materials.
SCIENCE CHINA-CHEMISTRY
(2021)
Article
Chemistry, Applied
C. Zippel, Z. Hassan, A. Q. Parsa, J. Hohmann, S. Brase
Summary: The method of kinetic resolution of 4-acetyl[2.2] paracyclophane via ruthenium-catalyzed enantioselective hydrogenation has been successfully realized, providing enantiomerically pure derivatives with high yields, which are useful for the production of chiral compounds.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Physical
Yin-Sheng Lin, Hsin Li, Wen-Sheng Yu, Szu-Tan Wang, Yi-Min Chang, Tsung-Hsin Liu, Shao-Sian Li, Motonori Watanabe, Hsiao-Han Chiu, Di-Yan Wang, Yuan Jay Chang
Summary: This study demonstrates that using novel WS-HTMs instead of spiro-OMeTAD can enhance the performance of perovskite solar cells, with devices based on WS-1 and WS-2 HTMs showing better power conversion efficiency and stability. By improving hole mobility and charge transfer efficiency, WS-HTMs achieved good results.
JOURNAL OF POWER SOURCES
(2021)
Article
Polymer Science
Jiangbo Lv, Yun Luo, Hang Xiao, Bo Liang, Li Chen, Xian He, Ke Zeng, Gang Yang
Summary: The curing behavior of addition curing polymer CN-PcP, containing [2.2]paracyclophane and phthalonitrile, was studied. Results showed that the carbon radical from [2.2]paracyclophane at high temperature could effectively promote the curing reaction of phthalonitrile, resulting in a cured resin with high glass transition temperature and outstanding thermal properties. Thermogravimetric analysis (TGA) and dynamic mechanical analysis (DMA) were performed to evaluate the thermal properties of the cured resin.
Article
Chemistry, Multidisciplinary
Jun Pu, Lei Chen, Rui-Rui Wu, Peng Ye, Huan-Le Li, Shuang Wang, Zhen-Yuan Xu, Shao-Jie Lou, Dan-Qian Xu
Summary: This paper reports the palladium-catalysed mono-selective C-H arylation of [2.2]paracyclophane (PCP) with diverse aryl iodides in the absence of pendant directing groups, providing a straightforward and modular access to C4-arylated [2.2]paracyclophanes. Furthermore, a new PCP-containing biaryl monophosphine complex can be readily obtained through further derivation of the arylated product.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Multidisciplinary
Campbell F. R. Mackenzie, Lucie Delforce, D. Rota Martir, David B. Cordes, Alexandra M. Z. Slawin, Eli Zysman-Colman
Summary: A 1D coordination polymer consisting of silver(I) ions bound to a [2.2]paracyclophane scaffold functionalized with two 4-pyridyl units has been synthesized and characterized. The structure of the polymer reveals two different silver coordination motifs that alternate along the 1D coordination polymer, exhibiting strong blue and sky-blue fluorescence in solution and in the crystalline solid state.
FRONTIERS IN CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Motonori Watanabe, Yuka Ono, Tatsumi Ishihara, Yuan Jay Chang, Masahiko Shibahara
Summary: Novel donor-acceptor dyads were synthesized and used to fabricate dye-sensitized hydrogen production systems. The [2.2]PCP moiety exhibited stronger electron-donating properties compared to the [3.3]PCP moiety, resulting in effective charge transfer and hydrogen generation.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Review
Biochemistry & Molecular Biology
Wenjing Liu, Huabin Li, Yanmin Huo, Qingxia Yao, Wenzeng Duan
Summary: In recent years, the [2.2]paracyclophane (PCP) ring has attracted extensive attention due to its features of providing chirality and steric hindrance, which improves the fluorescence properties of dyes. This review summarizes and promotes the application of PCP in fluorescent dye design, fluorescence detection, and CPL modulation, with a hope to enhance the understanding and improvement of fluorescent dye design.
Article
Chemistry, Multidisciplinary
Ksenia Reznikova, Chunwei Hsu, Werner M. Schosser, Almudena Gallego, Katawoura Beltako, Fabian Pauly, Herre S. J. van der Zant, Marcel Mayor
Summary: The correlation between substitution pattern, conductance, and mechanosensitivity in [2.2]paracyclophane (PCP)-based molecular wires was investigated in a mechanically controlled break junction experiment. It was found that para-phenyl-coupled anchoring in the PCP core leads to large variations in conductance values with changes in electrode separation, while this mechanosensitivity is absent for the meta-PCP core. The experimental findings were interpreted in terms of quantum interference effects between molecular frontier orbitals.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Physical
Mihail Lucian Birsa, Henning Hopf, Peter G. Jones, Laura Gabriela Sarbu, Lucian Gabriel Bahrin
Summary: Several new di- and tetracarboxylic [2.2]paracyclophane derivatives were synthesized through Suzuki coupling reactions. One of the products, pp-bis(4-carboxyphenyl)[2.2]paracyclophane (12), reacted with zinc nitrate to form a 2D coordination polymer with zinc-carboxylate paddlewheel clusters linked by cyclophane cores. The zinc center exhibited a five-coordinate square-pyramidal geometry.
Article
Chemistry, Organic
Shiru Yuan, Chen Liao, Wen-Hua Zheng
Summary: In this study, planar chiral [2.2]paracyclophane-based isothiourea catalysts were synthesized in a few simple steps with high yields. These catalysts showed highly efficient catalytic enantioselective fluorination of carboxylic acids, providing a broad range of optically active alpha-fluoroesters in high yield and excellent enantioselectivity.
Article
Polymer Science
Jiangbo Lv, Hang Xiao, Xian He, Zhengzhu Zhu, Menghao Chen, Wenjie Yang, Jianghuai Hu, Ke Zeng, Gang Yang
Summary: A new functionalized cyclophane derivative, DCI-PcP, has been designed and prepared, showing excellent thermal properties and processability.
Article
Chemistry, Organic
Dan Xu, Wen-Hua Zheng
Summary: Three pairs of planar chiral heteroarenes were synthesized from optically pure 4-amino[2.2]paracyclophane using palladium-catalyzed Buchwald-Hartwig coupling and hypervalent iodine-mediated oxidative cyclization. Among them, one enantiomer of planar chiral azahelicene was found to exhibit significantly stronger circularly polarized luminescence activity compared to the other planar chiral heteroarenes.
Article
Chemistry, Multidisciplinary
Kentaro Tanaka, Ryo Inoue, Yasuhiro Morisaki
Summary: By utilizing enantiopure building blocks, optically active cyclic dimers, trimers, and tetramers were prepared, showing clear Cotton effects and corresponding CPL signs. While the cyclic dimer did not emit CPL, the cyclic trimer and tetramer exhibited intense CPL emissions with a relatively high dissymmetry factor. Their optical and chiroptical properties were reproduced by time-dependent density functional theory calculations.
CHEMISTRY-AN ASIAN JOURNAL
(2022)
Article
Chemistry, Physical
Hiroki Ito, Katsuya Mutoh, Jiro Abe
Article
Chemistry, Multidisciplinary
Aya Kometani, Yuki Inagaki, Katsuya Mutoh, Jiro Abe
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2020)
Article
Chemistry, Multidisciplinary
Ryosuke Usui, Katsuya Yamamoto, Hajime Okajima, Katsuya Mutoh, Akira Sakamoto, Jiro Abe, Yoichi Kobayashi
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2020)
Article
Chemistry, Organic
Hiroki Ito, Sho Tanaka, Katsuya Mutoh, Jiro Abe
Article
Biochemistry & Molecular Biology
Sabina Brazevic, Stanislaw Nizinski, Michel Sliwa, Jiro Abe, Michal F. Rode, Gotard Burdzinski
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2020)
Article
Chemistry, Organic
Yasuki Kawanishi, Katsuya Mutoh, Jiro Abe, Yoichi Kobayashi
Summary: Novel fast photochromic PTIC derivatives were developed, forming charge transfer states and neutral open-shell transient species upon light irradiation. Extending the lifetimes of CT states through substitution altered their optical properties and chemical reactivities. Developing fast T-type photochromic molecules generating long-lived CT forms is crucial for expanding applications of fast photoswitching materials.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Moe Nishijima, Katsuya Mutoh, Jiro Abe
Summary: This study proposes a relationship between the diradical character and radical-radical coupling reaction rate of the light-induced radical pair of photochromic biimidazoles, and suggests that the aromaticity of the bridging unit connecting two imidazole rings can alter the diradical character and accelerate the reaction rate.
Article
Chemistry, Multidisciplinary
Katsuya Mutoh, Shota Toshimitsu, Yoichi Kobayashi, Jiro Abe
Summary: The study investigates the stepwise photochromic properties of biphotochromic molecules involving multiple spin interactions using double-pulse laser flash photolysis. The photochromic reaction generates the o-biradical form which thermally isomerizes to the o-quinoidal form and reaches thermal equilibrium between them. Additional photon absorption by the open-closed form leads to the generation of unpaired spins at the p-position of the central aromatic bridge of the biradical or quinoidal form, resulting in dynamic spin-spin interactions and rearrangement of chemical bonds.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Applied
Sabina Brazevic, Marek Sikorski, Michel Sliwa, Jiro Abe, Michal F. Rode, Gotard Burdzinski
Summary: The photochromic reaction of 8H-pyranoquinazoline has unique characteristics compared to 3H-naphthopyrans. The stabilized excited singlet state of 8H-pyranoquinazoline has a longer lifetime and is highly sensitive to solvents. The polar solvent acetonitrile reduces the quantum yield of the colored isomer formation. The color fading related to the decay of the transoid-cis population in 8H-pyranoquinazoline is faster compared to the 3H-naphthopyran family.
Article
Chemistry, Organic
Katsuya Mutoh, Jiro Abe
Summary: We have developed a stepwise photochromic imidazole dimer bridged by a sulfur atom. One-photon absorption leads to the formation of a colored biradical species, which quickly recombines to the original imidazole dimer following first-order reaction kinetics. The biradical species undergoes further photochemical reactions to produce a long-lived colored species, which displays intermolecular dimerization.
Article
Chemistry, Multidisciplinary
Ryuichi Sugimoto, Souma Konishi, Hiroki Saitoh, Atsushi Kimoto
Summary: A new class of rigid and planar compounds, carbazole-fused thioindigo oligomers (Cz(n)TI(n)11, n = 2, 3), was synthesized via palladium-catalyzed carbon-sulfur bond formation and intramolecular Friedel-Crafts acylation. The study focused on the reaction conditions for thioindigo moiety formation and the photoelectrochemical properties of the oligomers, including their photochromic behavior.
Article
Biochemistry & Molecular Biology
Katsuya Mutoh, Katsuya Yamamoto, Jiro Abe
Summary: In recent years, photochromic molecules with wavelength-selective or light intensity-dependent photoresponses have gained increasing attention. This study presents the design of stepwise two-photon induced photochromic molecules (PABI-PIC and PABI-PIC2) consisting of two different photochromic units. The stepwise photochromic properties of these molecules can be easily controlled depending on the excitation light intensity and wavelength. These molecular designs are important for the development of advanced photoresponsive materials.
PHOTOCHEMICAL & PHOTOBIOLOGICAL SCIENCES
(2022)
Article
Chemistry, Multidisciplinary
Yasuki Kawanishi, Yasutomo Segawa, Katsuya Mutoh, Jiro Abe, Yoichi Kobayashi
Summary: A carbazole-incorporated photochromic radical complex is synthesized, and the long-wavelength photosensitivity of the molecule is enhanced up to around 580 nm by substituting a triphenylamine group at the 3-position of the carbazole moiety. The photochromic reactions are investigated using subpicosecond-to-microsecond transient absorption measurements.
CHEMICAL COMMUNICATIONS
(2022)
Review
Chemistry, Multidisciplinary
Yoichi Kobayashi, Jiro Abe
Summary: Incoherent nonlinear photophysical and photochemical processes based on stepwise two-photon absorption (2PA) have been widely used in materials science due to their unique photoresponses. Nonlinear photochromic materials, in particular, have attracted considerable attention for their unconventional photoresponses and low power thresholds. This tutorial review introduces the concepts and applications of low-power-threshold nonlinear photochromic materials using stepwise 2PA processes. It provides a comprehensive understanding of the scientific progress in this field and offers a unified picture of the incoherent nonlinear optical properties of various photofunctional materials.
CHEMICAL SOCIETY REVIEWS
(2022)
Article
Chemistry, Multidisciplinary
Ruiji Li, Hiroki Arai, Yoichi Kobayashi, Katsuya Mutoh, Jiro Abe
MATERIALS CHEMISTRY FRONTIERS
(2019)
Article
Chemistry, Applied
Leping Chen, Yanfen Wang, Tingyu Shi, Tiantian Ma, Yang Li, Huayu Qiu, Shouchun Yin, Meier Gu
Summary: This study successfully overcame the limitations of the heavy atom effect by introducing iodine atoms and innovatively enhancing the structure while weakening stacking behavior, achieving high efficiency and precision in photodynamic therapy and photothermal therapy.
Article
Chemistry, Applied
Bingpeng Guo, Honghan Sa, Peng Zhang, Guiwen Hao, Mengyu Li, Qingqing Jiang, Baoying Li, Wei Shu, Changxiang Shao
Summary: The design of ratiometric fluorescence probes with large Stokes shift is of great significance in detecting and imaging target substances in complex organisms. In this study, a novel fluorophore with a large Stokes shift was easily obtained, and a fluorescence probe based on it demonstrated rapid response, high selectivity, and sensitivity towards peroxynitrite. The probe also showed excellent biocompatibility and remarkable mitochondrial targeting ability, making it suitable for proportional imaging of peroxynitrite in living cells and zebrafish.
Review
Chemistry, Applied
Haidong Huang, Xiaohui Wang, Xinyang Li, Yichen Li, Guojin Liu, Lan Zhou, Jianzhong Shao
Summary: This article introduces the application of responsive photonic crystals in anti-counterfeiting technology, with a focus on the preparation principle, classification, and preparation methods.
Article
Chemistry, Applied
Yunpeng Wang, Tao Zhao, Xiaoye Bi, Chencheng Lv
Summary: In this study, three novel carbene dyes were designed to achieve environmentally friendly dyeing processes. The dyes formed covalent bonds with fibers and exhibited good dyeing performance and high color fastness. These findings highlight the potential of the novel carbene dyes in promoting green production in the textile industry.
Review
Chemistry, Applied
Yizhe Yan, Xiaopei Zhu, Jia-Xin Cao, Yuan He, Shaoqing Li, Jian-Yong Wang
Summary: In this paper, 1,3,5-triazine dyes were successfully synthesized and their photophysical properties were studied. Two probes were selected for further investigation, showing promising applications in various fields.
Article
Chemistry, Applied
Xin Hu, Tongsheng Huang, Lihua Chen, Weifeng Zhu, Fengjie Deng, Xiancai Li, Jianwen Tian, Meiying Liu, Xiaoyong Zhang, Yen Wei
Summary: This study presents the synthesis of fluorescent cyclomatrix polyphosphazene spheres with aggregation-induced emission (AIE) feature and biodegradable potential for controlled drug delivery. The resulting micelles exhibit high water dispersibility, desirable fluorescence performance, and high drug loading capacity. They can effectively release the encapsulated drug in physiological solution and show excellent biological imaging ability and cytotoxicity against cancer cells.
Article
Chemistry, Applied
Yanzhu Liu, Yanghui Lei, Dongyan Li, Guangkui Li, Dongping Li, Yongxiu Li
Summary: In this study, luminescent lanthanide nanoparticles were synthesized as a dual emission turn-off probe for detecting 2,6-pyridinedicarboxylic acid (DPA) in water. The nanoparticles showed good dispersion and water stability, and achieved low detection limits for DPA. They also exhibited high recoveries in various samples.
Article
Chemistry, Applied
Jung Jae Do, Jong Ryeol Kwon, Donghan Kim, Jae Woong Jung
Summary: This study presents a defect passivation approach using coumarin dye as a multi-functional passivating agent of perovskite films to boost power conversion efficiency and operating stability of PSCs. The incorporation of coumarin dye improves the film morphology, enhances carrier extraction/transport, and suppresses trap-assisted recombination in the perovskite films. The optimized device demonstrates impressive reliability and practical applicability, maintaining over 90% of its initial PCE after being exposed to continuous indoor lighting irradiation for 2000 hours.
Article
Chemistry, Applied
Gang Wang, Yu-Chang Wang, Jing Lu, Wen-Fu Yan, Juan Jin, Yuan-Peng Wang, Jia-Jia Zhang, Hui-Jie Zhang, Hao Dong, Xi-Guang Liu
Summary: A new Ni(II) compound with good solid-state fluorescence performance and stability was synthesized, and it showed outstanding detection properties for various substances in aqueous solutions. This compound has the potential to be a multifunctional sensor.
Article
Chemistry, Applied
Luyao Wei, Shenglong Shang, Yu Zheng, Jie Liu, Ping Zhu
Summary: This study developed a facile method to create high saturation and durable structural colors on cotton fabrics. The colors are regulated by adjusting the size of magnetic particles and can be conveniently printed on fabrics using photo masks on transparent films.
Article
Chemistry, Applied
Zhao Jiang, Qing Zhang, Zhaoyu Kong, Ruijie Qiao, Zichuan Liu, Linzhou Song, Senqiang Zhu, Rui Liu, Hongjun Zhu
Summary: Three heteroleptic Ir(III) complexes with different electron-donating aryl groups were synthesized and their optical properties were investigated. It was found that all three complexes exhibited aggregation-induced phosphorescence emission (AIPE) behaviors, and the relationship between the size of organic ligands and AIPE behaviors was characterized. Ir-PhCz showed the best imaging of latent fingerprints due to its green light emission and high quantum yield.
Article
Chemistry, Applied
Zhijun Ruan, Chunxia Fan, Xuanrong Wang, Dong Shao, Xiaodong Yang, Wentao He, Tao Xu, Junqi Lin, Zhengfang Tian
Summary: A novel thioketal-based probe has been designed for rapid and accurate detection of mercury (II) ions, showing different fluorescence characteristics in various states. The probe exhibits excellent selectivity and specificity, making it suitable for Hg2+ detection in water solutions.
Article
Chemistry, Applied
Jianjun Huang, Xuan Zhao, Daniel Escudero, Luc Van Meervelt, Dongbin Zheng, Yuyu Fang, Wim Dehaen
Summary: A series of BOAHY compounds were successfully synthesized and showed versatile applications as a platform for designing novel fluorescent probes, especially in selective recognition.
Article
Chemistry, Applied
Roman V. Larkovich, Victoria E. Shambalova, Savva A. Ponomarev, Alexander S. Aldoshin, Boris N. Tarasevich, Konstantin A. Lyssenko, Valentine G. Nenajdenko
Summary: An efficient synthetic protocol for the preparation of novel 1,7-difluorinated BODIPYs was elaborated. Their photophysical properties were studied and the effect of 2,6-substituents was evaluated using DFT calculations.
Article
Chemistry, Applied
Haneul Kim, Byungjin Koo
Summary: In this study, a lithium ion sensing methodology based on fluorinated naphthalene compounds using 19F NMR and UV-vis spectroscopy is reported. The binding of lithium ions to the compounds is confirmed by changes in chemical shifts and peak broadening. Additionally, the effect of different crown ether ring sizes on the binding ability is observed. This study provides a new method for lithium ion sensing using spectroscopy.
