Article
Chemistry, Multidisciplinary
Yukui Tian, Bin Chen, Sixun Jiang, Ming Yuan, Jie Ren, Feng Wang
Summary: A bimetallic alkynylplatinum(ii) terpyridyl complex bridged by [2.2]paracyclophane shows severe emission quenching due to intramolecular pi-pi interactions. However, it undergoes an adaptive conformational change upon binding Ag+, which weakens the intramolecular stacking strength and results in turn-on emission.
CHEMICAL COMMUNICATIONS
(2021)
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, Organic
Shun Irii, Takuya Ogaki, Hana Miyashita, Kazutaka Nobori, Yoshiki Ozawa, Masaaki Abe, Hiroyasu Sato, Eisuke Ohta, Yasunori Matsui, Hiroshi Ikeda
Summary: This study investigates the piezofluorochromism (PFC) of crystals of a tert-butyl and [2.2]paracyclophane-containing diaroyl-methanatoboron difluoride (pCP-tBu) and finds that the crystals exhibit remarkable PFC associated with a redshift of fluorescence wavelength under increasing isotropic pressure. X-ray crystallographic analysis reveals the presence of intermolecular pi-stacking dimers in the crystal. High-pressure data shows a reduction in both the intermolecular pi-stacking distance of the dimer and the intramolecular pi-stacking distance. Density functional theory calculations suggest that the reduction of the LUMO energy of the pi-stacking dimer is the origin of PFC in pCP-tBu crystals.
TETRAHEDRON LETTERS
(2022)
Article
Chemistry, Multidisciplinary
Tao Chen, Guangjun Xiao, Zhuo Wang, Jian Zou, Jian Wang, Weibo Hu, Yahu A. Liu, Hui Yang, Ke Wen
Summary: Integrating fluorescent chromophores into aromatic frameworks can prevent aggregation-induced quenching and impart new fluorescence properties. In this study, s-tetrazine-bridged aromatic frameworks (TzAF) were fabricated by incorporating the smallest aromatic fluorophore, s-tetrazine (Tz), into the lattice of aromatic frameworks. The TzAF thin films exhibited reversible photoswitching fluorescence characteristics with excellent stability and high on/off contrast due to light-induced reversible transformation between TzAF's neutral and radical states.
Article
Materials Science, Multidisciplinary
Meng-Yuan Zhang, Qian Peng, Cui-Hua Zhao
Summary: The paper presents reversible and high-contrast mechanochromic luminescence properties of a triarylborane-based [2.2]paracyclophane, demonstrating remarkable fluorescence changes with high fluorescence quantum yields. The compound's rigid and congested structure helps to suppress intermolecular interactions, allowing intense fluorescence in both morphological phases. Theoretical calculations suggest two-color fluorescence switching due to different degrees of structural relaxation in the excited state.
JOURNAL OF MATERIALS CHEMISTRY C
(2021)
Article
Materials Science, Multidisciplinary
Ana-Maria Manea-Saghin, Carla-Cezarina Paduretu, Francois Kajzar, Cosmina Andreea Marin
Summary: This study discusses the linear and nonlinear optical properties of two organic molecules, including optical absorption, fluorescence, and third-order nonlinear optical (NLO) susceptibilities. The results show that these molecules have a wide transparency range in the visible spectrum and an enhancement of third-order NLO susceptibility at a specific wavelength.
MATERIALS CHEMISTRY AND PHYSICS
(2021)
Article
Chemistry, Applied
Ying-Chen Duan, Ying Gao, Xiao-Xia You, Yong Wu, Yun Geng, Yue-Gang Fu, Zhong-Min Su
Summary: The TADF nature of [2.2]paracyclophane derivatives with spatially conjugated structures was studied, revealing the influence of the conjugated structure on their optical properties. The design of new molecules resulted in potential efficient red-light TADF materials with enhanced radiation rate and decreased internal conversion rate.
Article
Chemistry, Multidisciplinary
Sundaravel Vivek Kumar, Patrick J. Guiry
Summary: We have developed a facile synthetic route for a novel series of imidazolinyl-[2.2]paracyclophanol (UCD-Imphanol) ligands with central and planar chirality. These ligands showed excellent activities and selectivities in asymmetric reactions, leading to enantioenriched pyrrolidines with high yields.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
David Weinzierl, Mario Waser
Summary: This protocol utilizes an ammonium ylide-mediated approach to achieve high yields and diastereoselectivity without the use of chiral ammonium salts, while switching to chiral salts enables high enantioselectivity and diastereoselectivity, accompanied by kinetic resolution of the racemic aldehyde starting material.
HELVETICA CHIMICA ACTA
(2021)
Article
Agricultural Engineering
Heyu Zhang, Ji Fan, Wei Wang, Dan Yu
Summary: This study develops smart cotton fabrics with synchronous positive and negative photochromic and fluorescent color-changing properties, which can respond to both visible and ultraviolet light. Photochromic cotton fabrics have potential applications in various fields, such as UV protection, pattern switching, and information encryption.
INDUSTRIAL CROPS AND PRODUCTS
(2023)
Article
Chemistry, Organic
Shou-Chih Huo, Ranadheer Reddy Indurmuddam, Bor-Cherng Hong, Chuan-Fu Lu, Su-Ying Chien
Summary: A new thioxanthone-based photocatalyst with a [2.2]paracyclophane skeleton and planar chirality has been developed and successfully applied in visible light-mediated enantioselective reactions to produce azetidines. The structures of the catalyst derivatives were unequivocally determined by single crystal X-ray crystallography analysis.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Physical
Johannes Maier, Tina Weller, Mukundan Thelakkat, Jurgen Koehler
Summary: Light-induced conversion of photochromic molecules has been intensively studied for various applications, showing high fatigue resistance and potential for super-resolution optical microscopy on frozen biological samples.
JOURNAL OF CHEMICAL PHYSICS
(2021)
Article
Chemistry, Inorganic & Nuclear
Kangting Zheng, Yajing Ye, Yanan Shi, Yaxuan Xu, Ziyu Yang, Pengtao Ma, Jingping Wang, Jingyang Niu
Summary: The translation discusses the preparation and properties of three isostructural DL-serine covalently function-alized and multinuclear lanthanide-embedded arsenotungstates. The compounds exhibit photochromic transformation from colorless to blue, and luminescent properties with energy migration to Sm3+ and Eu3+ ions.
INORGANIC CHEMISTRY
(2022)
Article
Chemistry, Inorganic & Nuclear
Kangting Zheng, Yajing Ye, Yanan Shi, Yaxuan Xu, Ziyu Yang, Pengtao Ma, Jingping Wang, Jingyang Niu
Summary: The synthesis and characterization of three isostructural arsenotungstates with photochromic properties are reported, and the luminescent behavior and energy migration of one of the compounds are investigated.
INORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Nanami Miki, Ryo Inoue, Yasuhiro Morisaki
Summary: In this study, both enantiomers of a one-handed helical molecule with an o-arylene-ethynylene skeleton were prepared using a planar chiral [2.2]paracyclophane, and the helicity of the molecule was controlled by its planar chirality. Excellent chiroptical properties, especially intense circularly polarized luminescence with a high g(lum) value on the order of 10(-2), were observed.
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN
(2022)
Article
Chemistry, Multidisciplinary
Xiaolei Zhu, Cheriehan Hessin, Aude Salame, Lydia Sosa-Vargas, David Kreher, Chihaya Adachi, Anna Proust, Pierre Mialane, Jerome Marrot, Aude Bouchet, Michel Sliwa, Stephane Mery, Benoit Heinrich, Fabrice Mathevet, Guillaume Izzet
Summary: The synthesis and characterization of the first mesogenic donor-acceptor polyoxometalate (POM)-based hybrid were described. In the solid state, the compound exhibited birefringent behavior with lamellar organization, and the fluorescence of the organic donor unit was significantly quenched, attributed to the occurrence of an intramolecular charge-separated state.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(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
Biochemistry & Molecular Biology
Adjele Wilson, Elena A. Andreeva, Stanislaw Nizinski, Lea Talbot, Elisabeth Hartmann, Ilme Schlichting, Gotard Burdzinski, Michel Sliwa, Diana Kirilovsky, Jacques-Philippe Colletier
Summary: This study reports on the characteristics of Plankto-OCP, a variant of the orange carotenoid protein (OCP) involved in cyanobacterial photoprotection. Plankto-OCP shows higher photoactivation and recovery rates, stronger energy-quenching activity, and is affected by the presence of a his-tag and the functionalizing carotenoid. The structures of Plankto-OCP reveal its molecular breathing motions and potential structural changes that explain its unique properties.
BIOCHIMICA ET BIOPHYSICA ACTA-BIOENERGETICS
(2022)
Article
Chemistry, Multidisciplinary
Moe Nishijima, Katsuya Mutoh, Rintaro Shimada, Akira Sakamoto, Jiro Abe
Summary: We propose a rational method for evaluating the diradical character of the photochromic phenoxyl-imidazolyl radical complex (PIC) derivatives based on their radical-radical coupling reaction rates. By changing the aromaticity and substitution position of the bridging unit, it is possible to control the contribution of open-shell diradical and closed-shell quinoidal structures to the open-ring isomer. The radical recombination reaction rate of the open-ring isomer is an excellent parameter of the diradical character.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Multidisciplinary
Hiroki Ito, Katsuya Mutoh, Jiro Abe
Summary: This article introduces a negative photochromic molecule NPy-ImD with three different isomers, which can generate different colored isomers under blue and red light irradiation by BR. Its absorption bands can be selectively excited with different light sources, providing more versatility and control. It has the combined potential for both kinetic and thermodynamic reactions, making it highly applicable in photoresponsive systems.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Biochemistry & Molecular Biology
Nicolas Fabre, Tuyoshi Fukaminato, Arnaud Brosseau, Michel Sliwa, Remi Metivier
Summary: A diarylethene-perylenebisimide (DAE-PBI) dyad with bright red emission and large ON-OFF contrast was studied, and its excited state dynamics were characterized in solution and nanoparticle suspension. Efficient energy transfer between the fluorophore and photochromic unit was demonstrated, occurring in a few hundreds of femtoseconds.
PHOTOCHEMICAL & PHOTOBIOLOGICAL SCIENCES
(2023)
Article
Chemistry, Multidisciplinary
Katsuya Mutoh, Natsuho Moriyama, Jiro Abe
Summary: The development of visible or near-infrared (NIR) light-responsive fast photoswitchable molecules has attracted attention due to their non-invasive features for controlling physical and chemical properties of materials and biological tissues. A new molecular design was proposed to enhance the thermal back-reaction of a negative photochromic molecule, BN-ImD. Additionally, a novel photoreaction product with a unique eight-membered ring structure was generated by irradiating a BN-ImD derivative with visible light, providing intriguing insights for the future development of fast negative photochromic molecules.
CHEMICAL COMMUNICATIONS
(2023)
Article
Biophysics
Stanislaw Nizinski, Ilme Schlichting, Jacques-Philippe Colletier, Diana Kirilovsky, Gotard Burdzinski, Michel Sliwa
Summary: This study investigates the photoactivation mechanism of orange carotenoid protein (OCP) and observes the formation of OCPR under continuous light irradiation and nanosecond laser pulse excitation. The results suggest that the formation quantum yield of OCPR increases with photon flux density, indicating the consecutive absorption of two photons.
BIOPHYSICAL REPORTS
(2022)
Article
Chemistry, Multidisciplinary
Stanislaw Nizinski, Adjele Wilson, Lucas M. Uriarte, Cyril Ruckebusch, Elena A. Andreeva, Ilme Schlichting, Jacques-Philippe Colletier, Diana Kirilovsky, Gotard Burdzinski, Michel Sliwa
Summary: This study explores the photophysical properties of Orange Carotenoid Protein (OCP) and highlights the formation of excited states and the impact of different tags on its function. The research suggests that careful consideration of excitation power and tag position is necessary when comparing the photoactivation of various OCP variants.
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)