- Gating charge recombination rates through dynamic bridges in tetrathiafulvalene-fullerene architectures
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An open and shut case: The competition between charge separation and recombination in artificial photosynthetic systems can be controlled by using photochromic dynamic bridge. The photoinduced opening and closing of the bridge mediates the electronic coupling between donor (D) and acceptor (A). Copyright
- Castellanos, Sonia,Vieira, Andre A.,Illescas, Beatriz M.,Sacchetti, Valentina,Schubert, Christina,Moreno, Javier,Guldi, Dirk M.,Hecht, Stefan,Martin, Nazario
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Read Online
- Absolute stereochemistry and CD spectra of resolved enantiomers of the colored form of a photochromic dithienylethene
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The colored form of photochromic 1,2-bis(5-hydroxymethyl-2-methyl-3-thienyl)hexafluorocyclopentene was resolved into enantiomers by HPLC. The absolute stereochemistry of an enantiomer was determined on its bis(4-chlorobenzoate). The CD spectra and optical rotation of the resolved colored form were measured.
- Yokoyama, Yasushi,Hosoda, Naoya,Osano, Yasuko T.,Sasaki, Chizuko
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Read Online
- NOVEL COMPOUNDS HAVING INHIBITORY ACTIVITY ON PROSTAGLANDIN E2 RECEPTOR AND USES THEREOF
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The present application relates to a novel compound having inhibitory activity on prostaglandin E2 receptor and uses thereof, and provides a compound represented by formula I, a solvate, stereoisomer or pharmaceutically acceptable salt thereof, a pharmaceutical composition comprising the same, and a method of using the same.
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Paragraph 382-385
(2022/03/07)
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- Stabilization of ultra-small gold nanoparticles in a photochromic organic cage: modulating photocatalytic CO2reduction by tuning light irradiation
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Synthesis and stabilization of ultra-small metal nanoparticles (MNPs) composed of a few atoms are of paramount importance in modulating their material properties based on quantum confinement effects. The highly reactive surface of small MNPs tends to aggregate, resulting in bigger particles and subsequent deterioration of the catalytic activity. In this work, we exploited a dithienylethene (DTE) based photochromic organic cage (TAE-DTE) for thein situstabilization of ultra-small Au NPs (Au@TAE-DTE) (2reduction to CO. Importantly, irradiating with light of the full range (λ= 250-750 nm) allowed for co-existence of both photoisomers which thereby showed wide spectrum absorption as compared to individual photoisomers, consequently displaying substantially enhanced performance for the photocatalytic CO2reduction. Further, the real-time progress of the CO2reduction reaction and corresponding reaction intermediates was detected by anin situDRIFT experiment.
- Singh, Ashish,Verma, Parul,Samanta, Debabrata,Dey, Anupam,Dey, Jyotirmoy,Maji, Tapas Kumar
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supporting information
p. 5780 - 5786
(2021/03/16)
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- Development of High-Performance Pyrimidine Nucleoside and Oligonucleotide Diarylethene Photoswitches
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Nucleosidic and oligonucleotidic diarylethenes (DAEs) are an emerging class of photochromes with high application potential. However, their further development is hampered by the poor understanding of how the chemical structure modulates the photochromic properties. Here we synthesized 26 systematically varied deoxyuridine- and deoxycytidine-derived DAEs and analyzed reaction quantum yields, composition of the photostationary states, thermal and photochemical stability, and reversibility. This analysis identified two high-performance photoswitches with near-quantitative, fully reversible back-and-forth switching and no detectable thermal or photochemical deterioration. When incorporated into an oligonucleotide with the sequence of a promotor, the nucleotides maintained their photochromism and allowed the modulation of the transcription activity of T7 RNA polymerase with an up to 2.4-fold turn-off factor, demonstrating the potential for optochemical control of biological processes.
- Kolmar, Theresa,Büllmann, Simon M.,Sarter, Christopher,H?fer, Katharina,J?schke, Andres
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supporting information
p. 8164 - 8173
(2021/03/08)
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- Preparation method of near-infrared absorption amphiphilic diene photochromic molecule and reversible photo-thermal method Application of photoacoustic
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The invention discloses preparation of a near-infrared absorption amphiphilic diene photochromic molecule and application of reversible photo-thermal and photoacoustic, and belongs to the technical field of functional materials. The structure is as follows. or. In-flight R1 , R2 , R3 Are all selected from C1 - C6 A straight-chain alkyl group. The photochromic protein nanoparticles assembled with albumin can be used for preparing photothermal therapeutic materials and photoacoustic contrast agents.
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Page/Page column 16; 20-21
(2021/11/10)
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- Diarylethene compound, preparation and applications thereof
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The invention relates to a diarylethene compound, preparation and applications thereof, and specificallydiscloses a compound represented by a formula (A), wherein various groups are defined in the specification. According to the invention, the compound is an excellent photochromic compound, and can be subjected to a photoisomerization reaction under the irradiation of light with specific wavelength to generate a ring-closing compound; and the compound and the photoisomerized ring-closing derivative thereof have high activity on agricultural and forestry pests such as aphids, aedes albopictus larvae of NematoceraCulicidae, and the like, and the activity of the ring-closing compound after illumination is higher than the activity of the ring-opening compound before illumination.
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Paragraph 0187-0190
(2020/01/25)
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- Photoswitchable J-aggregated processable organogel by integrating a photochromic acceptor
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A novel αchromophoric 1,4-bis(anthracenylethynyl)benzene (BAB)-based highly emissive J-aggregated organogel has been synthesized and characterized. Single-crystal structure determination of asymmetric π-chromophoric bola-amphiphilic BAB1 (dodecyl and triethyleneglycolmonomethylether containing side chains of bis(anthracenylethynyl)benzene) supports J-aggregation. Further, a photochromic acceptor chromophore, 4,4′-(perfluorocyclopent-1-ene-1,2-diyl)bis(5-methylthiophene-2-carbaldehyde), is noncovalently encapsulated in the gel and photoswitching studies have been performed based on photochromic F?rster resonance energy transfer. The modulated emission of the processable soft material is further exploited for rewritable display. However, BAB2 (dodecyl side chain on both sides) does not show gelation property due to its low solubility.
- Samanta, Debabrata,Singh, Ashish,Verma, Parul,Bhattacharyya, Sohini,Roy, Syamantak,Maji, Tapas Kumar
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supporting information
p. 10946 - 10952
(2019/09/30)
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- Preparation method of diaryl heterocycle substituted hexafluorocyclopentene-based photochromic compound
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The invention relates to a preparation method of a diaryl heterocycle substituted hexafluorocyclopentene-based photochromic compound, and belongs to an organic photochromic material. The preparation method comprises: 1, synthesizing 5-methyl-4-bromo-2-thiophene formaldehyde diethanol; 2, synthesizing 1,2-dimethyl-5-R1-3-bromoindole; and 3, synthesizing a diaryl heterocycle substituted hexafluorocyclopentene-based photochromic compound. According to the present invention, the prepared diaryl heterocycle substituted hexafluorocyclopentene-based photochromic compound has the red shift of the absorption wavelength of 50-100 nm, is a thermally-irreversible bistable state, and can be used in the fields of optical information storage, anti-counterfeiting recognition, concealing materials and military camouflage materials.
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Paragraph 0043; 0045-0048
(2019/05/16)
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- Dental Materials With Light-Induced Reversible Coloring
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The invention relates to a radically polymerizable dental material having photochromic properties, which contains at least one compound of formula (I) and optionally radically polymerizable monomers, an initiator for radical polymerization and other components.
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Paragraph 0106; 0107; 0108; 0109
(2019/01/25)
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- Sensitive Assays by Nucleophile-Induced Rearrangement of Photoactivated Diarylethenes
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Upon light-induced isomerization, diarylethenes (DAEs) equipped with reactive aldehyde moieties rearrange selectively in the presence of amines, accompanied by decoloration. In a comprehensive study, the probe structure was optimized with regard to its inherent reactivity in the nucleophile-triggered rearrangement reaction. Detailed structure-reactivity relationships could be derived, in particular with regard to the type of integrated (het)aryl moieties as well as the location of the formyl residue, and the probes' intrinsic reactivity with primary and secondary amines was optimized. Utilizing an ancillary base, the initially formed rearrangement product can engage in a subsequent catalytic cycle, leading to an amplified decoloration process. This additional catalytic pathway allows us to enhance the sensitivity of our method and successfully discriminate between amines and thiols. Moreover, probes that exhibit strong analyte-induced fluorescence modulation have been designed to further decrease the detection limit by using a more sensitive read-out. The optimized DAE probes are promising molecular components for future programmable sensing materials and devices.
- Fredrich, Sebastian,Bonasera, Aurelio,Valderrey, Virginia,Hecht, Stefan
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p. 6432 - 6440
(2018/05/31)
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- Comprising benzimidazole group of asymmetric perfluoro pentene photochromic fluorescent probe compound and its preparation method and application
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The invention discloses an asymmetric perfluorocyclopentene photochromic fluorescent probe compound containing a benzimidazole group as well as a preparation method and an application of the asymmetric perfluorocyclopentene photochromic fluorescent probe compound. The photochromic material can keep good photochromic performance in a solution and a crystalline phase, has excellent performance such as good chemical and thermal stability, remarkable fatigue resistance, relatively high cyclizing quantum yield, relatively strong fluorescence property and very good sensitivity in an open loop state and a closed loop state in the solution, can be used for high-density holographic optical storage with storage attribute comparable with that of rewritable photon type storage and an symmetric type perfluorocyclopentene material, is relatively low in cost in preparation material and relatively great in application prospect.
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Paragraph 0024; 0027; 0028; 0029
(2017/08/25)
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- Diarylethene type photochromic insecticidal compound and preparation method and purpose thereof
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The invention relates to a diarylethene type photochromic insecticidal compound and a preparation method and a purpose thereof. Specifically, the invention discloses a compound as shown in formula (A) or an optical isomer or a cis-trans-isomer thereof, or an agricultural pharmaceutically acceptable salt, and the definitions of substituent groups are as stated in the description. The invention also discloses the preparation method and the purpose of the compound. The formula (A) is shown in the description.
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Paragraph 0148-0150
(2017/06/20)
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- Full Color Light Responsive Diarylethene Inks for Reusable Paper
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“Digitalization” represents one approach to shift society's dependence on paper-based communication. However, thus far, this tactic has not had a significant impact on global paper consumption, which has risen over the past few decades. The escalating demand of paper making and consumption has resulted in an intensified negative effect on the environment. Because of this, the development of rewritable paper or erasable ink appears to be an ideal approach to alleviate the increasing demand for paper. In the investigation described herein, novel light-stimulated (UV–vis), reversible color switching, photochromic diarylethene (DE) derivatives are designed, which serve as cyan, magenta, and yellow colored ink materials for full color ink-jet printing. The structures of the DE derivatives are unique in that they contain hydrophilic ethylene glycol chains that enable them to be compatible with aqueous based, ink-jet printing systems. The results of these studies demonstrate that the new DE derivatives can be used in a printing system based on the “write–erase–write” concept that utilizes the same paper multiple times. The approach appears to be ideal for reducing the negative environmental consequences of paper production and consumption.
- Jeong, Woomin,Khazi, Mohammed Iqbal,Park, Dong-Hoon,Jung, Young-Sik,Kim, Jong-Man
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p. 5230 - 5238
(2016/08/05)
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- Photochromic thiopheneglyoxylic luen cholic acid water-soluble symmetrical entire fluorine link pentene compound, preparation method and application
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The invention discloses a photochromic thiophene-linked cholic acid water-soluble symmetrical perfluorocyclopentene compound and a preparation method and application of the compound. The photochromic material can keep good photochromic property in a solution or a thin film and has fluorescence in the range of 350-550nm in an open-loop state; and furthermore, as the ultraviolet irradiation time is prolonged, the strength of a fluorescence emission spectrum is reduced. Thus, the photochromic material can be used for fluorescence detection and fluorescence light control switching; and compared with a symmetrical thiophene or benzothiophene type perfluorocyclopentene material, the compound has the advantages that the cost of the preparation materials is relatively low and the application prospects are relatively great.
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Paragraph 0023; 0025; 0026
(2017/02/09)
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- HETEROARYL COMPOUNDS USEFUL AS INHIBITORS OF SUMO ACTIVATING ENZYME
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Disclosed are chemical entities which are compounds of formula (I); or pharmaceutically acceptable salts thereof; wherein Y, Ra, Ra', Rb, Rc, X1, X2, X3, Rd, Z1, and Z2 have the values described herein and stereochemical configurations depicted at asterisked positions indicate absolute stereochemistry. Chemical entities according to the disclosure can be useful as inhibitors of Sumo Activating Enzyme (SAE). Further provided are pharmaceutical compositions comprising a compound of the disclosure and methods of using the compositions in the treatment of proliferative, inflammatory, cardiovascular, and neurodegenerative diseases or disorders.
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Paragraph 00296
(2016/01/25)
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- HETEROCYCLIC AMIDE DERIVATIVES AS EP4 RECEPTOR ANTAGONISTS
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The invention relates to compounds of Formula (I) (or pharmaceutically acceptable salts thereof) as defined herein, pharmaceutical compositions thereof, and their use in manufactures and methods for modulating biological processes including antagonism of Prostaglandin EP4 receptor as a therapeutic treatment.
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Paragraph 0119; 0120
(2016/04/26)
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- Nonsymmetrical 3,4-dithienylmaleimides by cross-coupling reactions with indium organometallics: Synthesis and photochemical studies
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The synthesis and photochemical study of novel nonsymmetrical 1,2-dithienylethenes (DTEs) with a maleimide bridge have been carried out. The synthetic approach to the DTEs was based on successive selective palladium-catalyzed cross-coupling reactions of 5-susbtituted-2-methyl-3-thiophenyl indium reagents with 3,4-dichloromaleimides. The required organoindium reagents were prepared from 2-methyl-3,5-dibromothiophene by a selective (C-5) coupling reaction with triorganoindium compounds (R3In) and subsequent metal-halogen exchange. The coupling reactions usually gave good yields and have a high atom economy with substoichiometric amounts of R3In. The results of photochemical studies show that these novel dithienylmaleimides undergo a photocyclization reaction upon irradiation in the UV region and a photocycloreversion after excitation in the visible region, thus they can be used as photochemical switches. ON-OFF operations can be repeated in successive cycles without appreciable loss of effectiveness in the process.
- Mosquera, ngeles,Frnandez, M. Isabel,Lopez, Moiss Canle,Sestelo, Jos Prez,Sarandeses, Luis A.
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supporting information
p. 14524 - 14530
(2015/01/09)
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- Enantioselective photochromism of diarylethenes in human serum albumin
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Making light work of chromism: Enantioselective photochromic ring-closing reactions of three bisthienylethene compounds possessing either no or two hydroxy groups were carried out in the hydrophobic pockets of human serum albumin (HSA) in aqueous media. When 10 equivalents of HSA were used, 1,2-bis(5-hydroxymethyl-2-methyl-3-thienyl)hexafluorocyclopentene predominantly produced the S,S closed form (see scheme; O=open, C=closed), in 63 % ee at RT and 71 % ee at -4°C upon irradiation with 313 nm light. Copyright
- Fukagawa, Mai,Kawamura, Izuru,Ubukata, Takashi,Yokoyama, Yasushi
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supporting information
p. 9434 - 9437
(2013/07/26)
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- Toward multi-addressable molecular systems: Efficient synthesis and photochromic performance of unsymmetrical bisthienylethenes
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Various synthetic routes have been compared to access to unsymmetrical 1,2-bisthienylperfluorocyclopentenes having one electro-withdrawing formyl group. The strategy based on key monosusbtituted cyclopentenes appears to be the most reliable and versatile
- Sevez, Guillaume,Pozzo, Jean-Luc
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experimental part
p. 246 - 253
(2011/09/12)
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- Effect of side chain substituents on the electron injection abilities of unsymmetrical perylene diimide dyes
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Three near-infrared (NIR) absorbing unsymmetrical perylene diimide D-A-D type dyes containing 6-undecanoxy as donor group were utilized in dye-sensitized nanocrystalline TiO2 solar cells. Structure of the acceptor side of the molecules were improved by adding 4-[2-methyl-5-(cyanoacrylic acid)-3-thienyl]-phenyl (V), 3-carboxy-2-pyridil (VI) and 3-carboxy-2-pyrazyl (VII) moieties attached to one of the N-side of the dye. The relationship between the molecular structure of the acceptor sites of the dyes and the photovoltaic performances were discussed. Electrochemical measurements indicated that band gaps of the dyes were energetically favorable for electron injection from the excited state of the dyes to the conduction band of TiO2 nanoparticles. However, three dyes gave lower conversion efficiency on DSSC applications. Strong electron-withdrawing nature of perylene core might not permit to transfer the photo-generated electrons to the carboxyl groups anchoring to TiO2 surface, and then solar-to-electricity conversion efficiencies of the dyes were reduced.
- Dinalp, Haluk,Akar, Zuhal,Zafer, Ceylan,Li, Sddk
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experimental part
p. 182 - 191
(2012/01/13)
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- FUSED HETEROCYCLIC COMPOUND
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The present invention aims to provide a glucokinase activator useful as a pharmaceutical agent such as an agent for the prophylaxis or treatment of diabetes, obesity and the like, and the like. A glucokinase activator containing a compound represented by the formula (I): wherein each symbol is as defined in the specification, or a salt thereof or a prodrug thereof.
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Page/Page column 36
(2009/07/18)
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- NITROGEN-CONTAINING BICYCLIC HETEROARYL COMPOUNDS AND METHODS OF USE
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The present invention comprises a new class of compounds capable of modulating Raf kinase and, accordingly, useful for treatment of Raf kinase mediated diseases, including melanomas, tumors and other cancer-related conditions. The compounds have Formula (I) wherein R1 is Formula (II), (III) or (IV) and A1, A2, A3, A4, X, Z, Z', R1, R2, R3, R4, R5 and R6 are defined herein. The invention further comprises pharmaceutical compositions, methods for treatment of Raf kinase mediated diseases, and intermediates and processes useful for the preparation of compounds of the invention.
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Page/Page column 124
(2008/06/13)
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- PYRIMIDINE DERIVATIVE
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A compound represented by the general formula (1) which has an inhibitory effect on PDE4 activity and produces little adverse side effects: wherein Ar1 represents a furyl, thienyl, triazolyl, thiazolyl, oxazolyl or benzothiazolyl group; Ar2 represents -E-AR21-G-Q (where Ar21 represents a benzene or naphthalene ring; E represents a single bond or an alkylene group; G represents a single bond, an alkylene group or an alkenylene group; and Q represents a carboxyl group, -CON(R41)(R42) or -COOR43), -E-Ar21-G2-G-Q (where E, Ar21, G and Q are as defined above; and G2 represents -O-, -S-, -SO-, -SO2- or -NRG21-) or a monocyclic aromatic heterocyclic ring other than a pyrazolyl group; R1 and R2 are the same as or different from each other and independently represent a hydrogen atom, an alkyl group which may be substituted or the like; and R3 represents a hydrogen atom or an alkyl group which may be substituted.
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Page/Page column 173
(2010/11/25)
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- Ring-opening and -closure reaction dynamics of a photochromic dithienylethene derivative
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The influence of a bulky, strongly coupled substituent (benzoyl-phenyl-ethenyl, BPE) on the dynamics of the photoinduced ring-closure and ring-opening reactions of 1,2-bis[[2-methyl-thien-3-yl]]perfluorocyclopentene (BMTFP) in solution was investigated. UV/vis absorption spectroscopy in combination with chemical actinometry was employed to determine the reaction quantum yields. The relaxation and reaction dynamics were studied by transient absorption spectroscopy, exciting the S0-S2 transition of the open isomer with pump pulses at 288 nm, while 657 and 410 nm pulses were used to excite the S1 and S2 states of the closed isomer, respectively. Transient absorption spectra in the range of 350-950 nm were recorded using temporally delayed, white-light continuum probe pulses. After structural relaxation in the S1 excited state, the ring-closure reaction takes place with high quantum yield through a conical intersection. This conical intersection acts also as relaxation funnel for the S1 excited state of the closed isomer, from which it is separated by an energy barrier. The branching in the conical intersection favors the closed isomer, so that the ring-opening reaction yield is small (10-3-10-4). This yield was found to vary by a factor of 6 for different isomers obtained by rotation around the ethylene bond of the substituent.
- Ern, Jan,Bens, Arthur T.,Martin, Hans-Dieter,Kuldova, Karla,Peter Trommsdorff,Kryschi, Carola
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p. 1654 - 1660
(2007/10/03)
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- Light-Triggered Molecular Devices: Photochemical Switching of Optical and Electrochemical Properties in Molecular Wire Type Diarylethene Species
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Organic photochromic systems represent a starting point for the elaboration of light-triggered molecular switching devices.The novel bispyridinium and bispyridine compounds 1(2+) and 6 were synthesized as their uncyclized isomers from 3,5-dibromo-2-methylthiophene in overall yields of 43 and 44percent, respectively.The diarylethene photochromes 2 and 10-13, substituted with electron donors and acceptors, were prepared from 5-methylthiophene-2-carboxaldehyde in 21-32percent overall yield.All of the compounds were found to exhibit pronounced photochromic properties.Irradiation with UV light resulted in essentially complete photocyclization of the open forms to the intensely coloured closed isomers which could, in turn, be reconverted back to the open state with visible light of λ > 600 nm.The absorption maxima of the discribed compounds in their closed forms are shifted far towards, and even into, the near-IR region.Whereas no thermochromic properties were observed for the open isomers, the rates of thermal decolouration of the cyclized forms was found to be highly dependent on the nature of the substituents on the thiophene rings.It was demonstrated that reversible photochemical interconversion between the two photochromic states could be used to effectively switch a number of physical properties.Thus, the molecules 1(2+) and 12 represent two kinds of redox switches, the former in reduction and the latter in oxidation, in which electron conduction is switched on in the closed state and off in the open state.Compound 12 may also be considered to be a photoswitchable analogue of tetrathiafulvalene type substances.On the other hand, compound 2 displays a marked increase in nonlinear optical activity on conversion from the open to the closed form.Such systems are prototypes of photoswitchable molecular wires where electron conduction and push-pull interaction can be reversibly modulated by an external stimulus, namely, irradiation by light. - Keywords: diarylethenes, molecular devices, nonlinear optics, photochromes, redox switches
- Gilat, Sylvain L.,Kawai, Stephen H.,Lehn, Jean-Marie
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p. 275 - 284
(2007/10/02)
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- Light-triggered Electrical and Optical Switching Devices
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The functional photoswitchable systems 1-3 and 12-15 display pronounced photochromic properties; the bis-pyridinium derivative 1 represents a prototype of a switched molecular wire which may be converted from an open unconjugated form to a closed electron-conducting state.
- Gilat, Sylvain L.,Kawai, Stephen H.,Lehn, Jean-Marie
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p. 1439 - 1442
(2007/10/02)
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- Photochromism of Heterocyclic Fulgides
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Aiming at practical uses of photochromic compounds as data-storage media, electron-donating (e.g. p-dimethylaminophenyl) and conjugate chain (e.g. p-dimethylaminostyryl) substituted heterocyclic fulgides, e.g. 2-1-(2-substituted 5-methyl-4-oxazolyl)ethyl
- Tomoda, Akihiko,Kaneko, Akira,Tsuboi, Hideki,Matsushima, Ryouka
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p. 1262 - 1267
(2007/10/02)
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