1468-95-7Relevant articles and documents
Light- and heat-triggered reversible luminescent materials based on polysiloxanes with anthracene groups
Han, Dongdong,Lu, Hang,Li, Wensi,Li, Yonghao,Feng, Shengyu
, p. 56489 - 56495 (2017)
In this study, reversible silicone elastomers were successfully developed by light-triggered dimerization and heat depolymerization of the anthryl groups. Polysiloxanes with anthryl groups were prepared from poly(aminopropylmethylsiloxane) (PAPMS) with electron-donating (9-anthracenylmethyl acrylate) and electron-withdrawing (anthracene-9-carboxylic acid) units. The cross-linking networks were formed with the via 4π-4π photo-cycloadditions of the anthryl groups upon the UV light excitation (365 nm). 9-Anthracenylmethyl acrylate or anthracene-9-carboxylic acid efficiently dimerized through the photodimerization of the anthryl groups in the organic solvents, which was proven by UV-vis spectra, NMR spectra, and LC/MS. The covalent bonds between pendant anthryl groups were cleaved after heating at 120 °C. Furthermore, repeatable dimerization-depolymerization conversion was confirmed. In addition, for the first time, we found that the sunlight can also initiate the cycloaddition, which was "greener" and more environment-friendly. The green luminescence was observed from the PAPMS-1 film instead of the quenching effect caused by aggregation after the cycloaddition. Thus, a colorful UV-light emitting diode (LED) cell was obtained by coating the films on the commercially available LED cell.
A simple and robust PET-based anthracene-appended O-N-O chelate for sequential recognition of Fe3+/CN– ions in aqueous media and its multimodal applications
Pandith, Anup,Choi, Jun-Hyeak,Jung, Ok-Sang,Kim, Hong-Seok
, p. 669 - 680 (2018)
A very simple, robust, and pico/nanomolar-sensitive 9,10-diethanolamine-substituted fluorescent Fe3+/CN– probe (PD) was synthesised, and its sensing abilities towards various ions were studied in mixed aqueous media. PD selectively recognised Fe3+ ions through a ‘turn on’ response with an excellent binding constant (Ka, 9.29 × 106 M?1) in 1:2 binding stoichiometry at pH 7.0 in phosphate-buffered saline (PBS). The in situ generated Fe3+·PD ensemble sequentially recognised CN– ions with an excellent binding constant (Ka 1.72 × 108 M?1) via a ‘turn off’ mode by extruding Fe3+ ions from the ensemble. The highly selective sequential ‘on-off’ responses towards Fe3+ and CN– ions were attributed to inhibition and restoration of photoinduced electron transfer (PET) and chelation-induced enhanced fluorescence (CHEF) effects from the chelating N and O heteroatoms. PD was able to detect Fe3+ and CN– ions in real water samples satisfactorily at picomolar to sub-nanomolar levels. A colorimetric assay based on pyrocatechol violet (PCV) was also able to detect Fe3+/CN– in a sequential manner (up to sub-micromolar level) by a change in colour from colourless to yellow/pale green without any interferences from other ions. Based on the complexation and decomplexation mechanism, bio-imaging photonic INHIBIT logic circuit strips were prepared for use under physiological conditions. In addition, solid-phase recognition of Fe3+/CN– ions was demonstrated using cost-effective paper-based strips.
Activation of promutagens by endogenous and heterologous sulfotransferases expressed in continuous cell cultures
Glatt, Hansruedi,Pauly, Karin,Piee-Staffa, Andrea,Seidel, Albrecht,Hornhardt, Sabine,Czich, Andreas
, p. 13 - 22 (1994)
various environmental chemical are metabolised to chemically reactive sulfuric acid esters, which may covalently bind to cellular macromoleculaes and induce mutations and tumours. This activation pathway is usually not taken into account in external xenobiotic-metabolising systems used in short-term tests. We therefore analysed the abilities of cytosols from mammalian cell lines to activate benzylic alcohols (1-hydroxymethylpyrene and 9-hydroxymethylanthracene) to mutagens detectable in Salmonella typhimurium TA98. No activation was observed in cell lines which are commonly used in mutagenicity and cell transformation assays, and only low activities were found in epithelial cell lines in culture. We have therefore constructed Chineses hamster V79-derived cell lines which stably express a heterologous sulfotransferase, rat hydroxysteroid sulfotransferase a. Cytosol of these cells effectively activated 1-hydroxymethylpyrene and 9-hydroxymethylanthracene to mutagens detected in S. pyphimurium. The hepatocarcinogen 6-hydroxymethylbenzopyrene induced gene mutations in sulfotransferase-expressing V79-derived cells, whereas it elicited only marginal effects in sulfotransferase-deficient control cells. The new cell lines may allow the detection of novel classes of mutagens, since some externally generated reactive sulfuric acid esters may not readily penetrate target cells due to their short life span and their ionization. - Keywords: Benzylic alcohols; Bioactivation; Sulfotransferase; Sulfuric acid esters; V79 cells
Experimental and DFT studies on the vibrational and electronic spectra of 9-anthracenemethanol
Kou, Shanshan,Zhou, Hu,Tang, Guodong,Li, Rongqing,Zhang, Yu,Zhao, Jianying,Wei, Changmei
, p. 768 - 775 (2012)
Vibrational spectral measurements were made for 9-anthracenemethanol. Optimized geometrical structure and harmonic vibration frequencies were computed based on ab initio and density functional theory B3LYP methods using 6-311G and LANL2DZ basis sets. The
A Photo-Triggered Traceless Staudinger–Bertozzi Ligation Reaction
Hu, Peng,Feng, Tianshi,Yeung, Chi-Chung,Koo, Chi-Kin,Lau, Kai-Chung,Lam, Michael H. W.
, p. 11537 - 11542 (2016)
The use of light to control the course of a chemical/biochemical reaction is an attractive idea because of its ease of administration with high precision and fine spatial resolution. Staudinger ligation is one of the commonly adopted conjugation processes that involve a spontaneous reaction between azides and arylphosphines to form iminophosphoranes, which further hydrolyze to give stable amides. We designed an anthracenylmethyl diphenylphosphinothioester (1) that showed promising Staudinger ligation reactivity upon photo-excitation. Broadband photolysis at 360–400 nm in aqueous organic solvents induced heterolytic cleavage of its anthracenylmethyl–phosphorus bond, releasing a diphenylphosphinothioester (2) as an efficient traceless Staudinger–Bertozzi ligation reagent. The quantum yield of such a photo-induced heterolytic bond-cleavage at the optimal wavelength of photolysis (376 nm) at room temperature is ≥0.07. This work demonstrated the feasibility of photocaging arylphosphines to realize the photo-triggering of the Staudinger ligation reaction.
The synthesis of a new type of anthracene DNA intercalator
Ostaszewski, Ryszard,Wilczynska, Edyta,Wolszczak, Marian
, p. 2995 - 2996 (1998)
A new type of DNA intercalator based on anthracene 3 was synthesized. Preliminary binding studies show high affinity of this probe to CT-DNA. Higher binding constant of this compound (4.0 x 104 M-1) as compared with that known for 9-aminomethylanthracene, is caused presumably by enhanced electrostatic interaction.
Aromatic thioesters as protecting groups for thiols against 1,2-didehydrobenzenes
Fowelin, Christian,Schuepbach, Bjoern,Terfort, Andreas
, p. 1013 - 1017 (2007)
Divalent sulfur compounds usually react with 1,2-didehydrobenzenes to give a palette of unspecific products. To identify a suitable protecting group for thiols under the reaction conditions typically used for the synthesis of triptycenes, that is, 1,2-didehydrobenzene generated in situ from 2-diazoniobenzenecarboxylate at elevated temperatures, a wide-ranging optimization study was conducted. Of several acyl groups investigated, the benzoyl group turned out to be optimal. The efficiency of this protecting group was demonstrated by the successful transformation of an electron-poor (thus unreactive) anthracene derivative to the corresponding triptycenethiol derivative. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.
Synthesis of corrole-fullerene dyads via [4 + 2] cycloaddition reaction
Li, Chengjie,Zhang, Jie,Liu, Xiujun,Zhou, Yongzhu,Sun, Dongming,Cheng, Ping,Zhang, Bao,Feng, Yaqing
, p. 40758 - 40762 (2014)
Three corrole-fullerene dyads were prepared by treating anthracene-functionalized corroles with fullerene. Their structures were characterized by 1D- and 2D-NMR spectra and mass spectra. In the preliminary photo physical study of 3a by fluorescence spectroscopy, the excited corrole unit was quenched due to the introduction of fullerene. TD-DFT calculation theoretically indicated that the electron transfer occurs from the excited corrole to fullerene. This journal is
Arene-ruthenium complexes with 2-(arylazo)phenol as ancillary ligand: Synthesis, characterization, and utilization in catalytic transfer-hydrogenation
Karmakar, Jit,Bhattacharya, Samaresh
, p. 39 - 44 (2019)
Reaction of 2-(arylazo)phenols (HL-R, where H represents the phenolic proton and, R = CH3, H and Cl) with [{Ru(p-cymene)Cl2}2] in the presence of triethylamine affords a group of three reddish-brown complexes of type [Ru(p-cymene)(L-R)Cl] in good yields. Structure of [Ru(p-cymene)(L-CH3)Cl] has been determined by X-ray crystallography. The 2-(arylazo)phenolate ligand (L-R) is coordinated to the metal center as a mono-anionic bidentate N,O-donor forming five-membered chelate ring. All the complexes are diamagnetic, and show characteristic 1H NMR signals. They also show intense absorptions in the visible and ultraviolet regions, which have been analyzed by TDDFT calculations. Cyclic voltammetry on the complexes shows two successive irreversible oxidations within 1.10–1.40 V versus SCE. The [Ru(p-cymene)(L-R)Cl] complexes are found to serve as efficient catalyst-precursor for the transfer-hydrogenation of aldehydes.
Porter,Suppan
, p. 3375,3377 (1966)
Unruh,Gliecher
, p. 2008,2009-2014 (1971)
Porphyrin-Cored Polymer Nanoparticles: Macromolecular Models for Heme Iron Coordination
Rodriguez, Kyle J.,Hanlon, Ashley M.,Lyon, Christopher K.,Cole, Justin P.,Tuten, Bryan T.,Tooley, Christian A.,Berda, Erik B.,Pazicni, Samuel
, p. 9493 - 9496 (2016)
Porphyrin-cored polymer nanoparticles (PCPNs) were synthesized and characterized to investigate their utility as heme protein models. Created using collapsible heme-centered star polymers containing photodimerizable anthracene units, these systems afford model heme cofactors buried within hydrophobic, macromolecular environments. Spectroscopic interrogations demonstrate that PCPNs display redox and ligand-binding reactivity similar to that of native systems and thus are potential candidates for modeling biological heme iron coordination.
PHOTOLYTIC COMPOUNDS AND TRIPLET-TRIPLET ANNIHILATION MEDIATED PHOTOLYSIS
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Paragraph 0026, (2021/04/17)
The invention provides novel photolytic compounds and prodrugs, nanoparticles and compositions thereof, and methods of conducting photolysis mediated by triplet-triplet annihilation.
Dual utility of a single diphosphine-ruthenium complex: A precursor for new complexes and, a pre-catalyst for transfer-hydrogenation and Oppenauer oxidation
Mukherjee, Aparajita,Bhattacharya, Samaresh
, p. 15617 - 15631 (2021/05/19)
The diphosphine-ruthenium complex, [Ru(dppbz)(CO)2Cl2] (dppbz = 1,2-bis(diphenylphosphino)benzene), where the two carbonyls are mutually cis and the two chlorides are trans, has been found to serve as an efficient precursor for the synthesis of new complexes. In [Ru(dppbz)(CO)2Cl2] one of the two carbonyls undergoes facile displacement by neutral monodentate ligands (L) to afford complexes of the type [Ru(dppbz)(CO)(L)Cl2] (L = acetonitrile, 4-picoline and dimethyl sulfoxide). Both the carbonyls in [Ru(dppbz)(CO)2Cl2] are displaced on reaction with another equivalent of dppbz to afford [Ru(dppbz)2Cl2]. The two carbonyls and the two chlorides in [Ru(dppbz)(CO)2Cl2] could be displaced together by chelating mono-anionic bidentate ligands, viz. anions derived from 8-hydroxyquinoline (Hq) and 2-picolinic acid (Hpic) via loss of a proton, to afford the mixed-tris complexes [Ru(dppbz)(q)2] and [Ru(dppbz)(pic)2], respectively. The molecular structures of four selected complexes, viz. [Ru(dppbz)(CO)(dmso)Cl2], [Ru(dppbz)2Cl2], [Ru(dppbz)(q)2] and [Ru(dppbz)(pic)2], have been determined by X-ray crystallography. In dichloromethane solution, all the complexes show intense absorptions in the visible and ultraviolet regions. Cyclic voltammetry on the complexes shows redox responses within 0.71 to -1.24 V vs. SCE. [Ru(dppbz)(CO)2Cl2] has been found to serve as an excellent pre-catalyst for catalytic transfer-hydrogenation and Oppenauer oxidation.
