633-70-5Relevant articles and documents
Soluble and easily crystallized anthracene derivatives: precursors of solution-processable semiconducting molecules
Park, Jong-Hwa,Chung, Dae Sung,Park, Jong-Won,Ahn, Taek,Kong, Hoyoul,Jung, Young Kwan,Lee, Jonghee,Yi, Mi Hye,Park, Chan Eon,Kwon, Soon-Ki,Shim, Hong-Ku
, p. 2573 - 2576 (2007)
New soluble anthracene derivatives containing thlophene and phenylenevlnylene derivatives were synthesized via well-known synthetic routes. TIPS derivatives were added at the 9,10-posltlons of anthracene for the solubility and crystailinlty. Both of the molecules were found to be promising for high charge mobility and stable organic semiconductors. The soluble anthracene core (TIPSAnt) Is a potential precursor for the synthesis of novel semiconducting materials.
Molecular Oxygen Activation by Redox-Switchable Anthraquinone-Based Metal-Organic Frameworks
De Carvalho, Jo?o Guilherme M.,Fischer, Roland A.,P?thig, Alexander
, p. 4676 - 4682 (2021)
A dipyridyl-substituted anthraquinone (2,6-di(pyridin-4-yl)-9,10-anthraquinone, DPAq) was incorporated as a redox-active linker molecule into crystalline coordination networks. The oxidation state of the organic linker can be selectively controlled prior to framework formation and furthermore be maintained in the solid state. Hydrogen bonding is identified to be a substantial stabilization factor. Additionally, it is shown that the anthraquinone-anthrahydroquinone redox pair can be switched reversibly even after incorporation in the solid state by a thermal treatment/soaking procedure - going along with the formation of hydrogen peroxide from molecular oxygen (air) during the oxidation process.
Effective side chain selection for enhanced open circuit voltage of polymer solar cells based on 2D-conjugated anthracene derivatives
Ai,Ouyang,Liu,Wang,Peng,Islam,Ge
, p. 73 - 80 (2015)
Two novel conjugated donor-acceptor polymers were synthesized by combining anthracene donor and benzothiadiazole acceptor with two different side chains (conjugated and non-conjugated). Their absorption spectroscopy, thermogravimetric analysis, electrochemical cyclic voltammetry, theoretical prediction, surface morphology, and photovoltaic performance were investigated. The resultant two-dimensional configuration showed good optical and electrochemical properties. By selectively introducing branched conjugated side chains and non-conjugated linear side chains on the polymer backbone, the highest occupied molecular orbital levels are low lying which results in an increased open circuit voltage for polymer solar cells. The open circuit voltage of 1.02 V in this work was among the highest value for anthracene-based polymer solar cells ever. Our results suggest a good way to regulate the molecular energy levels by selecting appropriate side chains.
A Dipolar Anthracene Dye: Synthesis, Optical Properties and Two-photon Tissue Imaging
Moon, Hyunsoo,Jun, Yong Woong,Kim, Dokyoung,Ryu, Hye Gun,Wang, Taejun,Kim, Ki Hean,Huh, Youngbuhm,Jung, Junyang,Ahn, Kyo Han
, p. 2518 - 2523 (2016)
Two-photon microscopy is a powerful tool for studying biological systems. In search of novel two-photon absorbing dyes for bioimaging, we synthesized a new anthracene-based dipolar dye (anthradan) and evaluated its two-photon absorbing and imaging properties. The new anthradan, 9,10-bis(o-dimethoxy-phenyl)-anthradan, absorbs and emits at longer wavelengths than acedan, a well-known two-photon absorbing dye. It is also stable under two-photon excitation conditions and biocompatible, and thus used for two-photon imaging of mouse organ tissues to show bright, near-red fluorescence along with negligible autofluorescence. Such an anthradan thus holds promise as a new class of two-photon absorbing dyes for the development of fluorescent probes and tags for biological systems.
CAPRYDAA, an anthracene dye analog to LAURDAN: A comparative study using cuvette and microscopy
Castro-Castillo, Vicente,Gajardo, Javier,Gratton, Enrico,Gunther, German,Malacrida, Leonel,Sanchez, Susana,Sandoval-Altamirano, Catalina
, p. 88 - 99 (2019)
We synthesized an anthracene derivative with solvatochromic properties to be used as a molecular probe for membrane dynamics and supramolecular organization. A nine carbon atom acyl chain and a dimethylamino substitution were introduced at positions 2 and 6 of the anthracene ring, respectively. This derivative, 2-nonanoyl-6-(dimethylamino)anthracene (termed CAPRYDAA), is a molecular probe designed to mimic the well-known membrane probe LAURDAN's location and response in the lipid membranes. Due to the larger distance between the electron donor and acceptor groups, its absorption and emission bands are red-shifted according to the polarity of the media. The photophysical behavior of CAPRYDAA was measured in homogeneous media, synthetic bilayer and cells, both in a cuvette and in a fluorescence microscope, using one and two-photon excitation. Our results show a comparable physicochemical behavior of CAPRYDAA with LAURDAN, but with the advantage of using visible light (488 nm) as an excitation source. CAPRYDAA was also excitable by two-photon laser sources, making it easy to combine CAPRYDAA with either blue or red emission probes. In GUVs or cells, CAPRYDAA can discriminate the lipid phases and liquid-liquid phase heterogeneity. This new membrane probe shows the bathochromic properties of the PRODAN-based probes designed by Weber, overcoming the need for UV or two-photon excitation and facilitating the studies on the membrane properties using regular confocal microscopes.
Triisopropylsilylacetylene-functionalised anthracene-alt-benzothiadiazole copolymers for application in bulk heterojunction solar cells
Cartwright, Luke,Taylor, Lois. J.,Yi, Hunan,Iraqi, Ahmed,Zhang, Yiwei,Scarratt, Nicholas. W.,Wang, Tao,Lidzey, David. G.
, p. 101607 - 101615 (2015)
Three triisopropylsilylacetylene-functionalised anthracene (TIPSAnt) based polymers were synthesised by copolymerising TIPSAnt with either dithienyl-5,6-difluoro-benzo[c]-[1,2,5]thiadiazole, dithienyl-benzo[c]-[1,2,5]thiadiazole or dibithiophenyl-benzo[c]-[1,2,5]thiadiazole to yield PTATffBT, PTATBT-8 and PTAT2BT-8, respectively. PTAT2BT-8 demonstrated a reduced optical and electrochemical band gap, relative to PTATffBT and PTATBT-8. The HOMO level of PTAT2BT-8 (-5.32 eV) is significantly shallower compared to its counterparts. This can be attributed to increased intramolecular charge transfer along the polymer backbone; a consequence of the incorporation of additional thiophene spacer units. The photovoltaic properties of the polymers were investigated by fabricating bulk heterojunction (BHJ) polymer solar cells using PC70BM as the electron acceptor. PTATffBT displayed limited solubility in common organic solvents and could not be used for the fabrication of photovoltaic cells. Optimised photovoltaic devices fabricated from PTATBT-8 and PTAT2BT-8 demonstrated power conversion efficiencies of 2.36% and 3.15%, respectively. PTAT2BT-8 provided better efficiencies chiefly as a result of better Jsc and FF values.
Anthracene based organic dipolar compounds for sensitized solar cells
Lin, Yan-Zuo,Huang, Chiung Hui,Chang, Yuan Jay,Yeh, Chia-Wei,Chin, Tsung-Mei,Chi, Kai-Ming,Chou, Po-Ting,Watanabe, Motonori,Chow, Tahsin J.
, p. 262 - 269 (2014)
Organic dyes that consist of an anthracene moiety between a triphenylamine donor group and a cyanoacrylic acid acceptor group displayed remarkable solar-to-energy conversion efficiency in dye-sensitized solar cells. The planar geometry of anthracene and its bulky substituents helped the dyes to form a high quality monolayer on the surface of TiO2. A typical device made with the dye AN-Bu displayed a maximal photon-to-current conversion efficiency (IPCE) 65% in the region of 350-510 nm, a short-circuit photocurrent density (Jsc) 12.78 mA cm-2, an open-circuit photovoltage (V oc) 0.73 V, and a fill factor (FF) 0.67, corresponding to an overall conversion efficiency 6.23%. In an experiment of using deoxycholic acid (DCA) as a co-absorbent, the values of Voc stayed in a similar range, yet the values of Jsc were reduced in ca. 11% due to a decrease of loading amounts. This result indicated that the quality of the dye films cannot be further improved by the adding of DCA. The photophysical properties were analyzed with the aid of a time-dependent density functional theory (TDDFT) model with the B3LYP functional.
Charge-Transfer-Induced Fluorescence Quenching of Anthracene Derivatives and Selective Detection of Picric Acid
Santra, Dines Chandra,Bera, Manas Kumar,Sukul, Pradip Kumar,Malik, Sudip
, p. 2012 - 2019 (2016)
2,6-Divinylpyridine-appended anthracene derivatives flanked by two alkyl chains at the 9,10-position of the core have been designed, synthesized, and characterized by NMR, MALDI-TOF, FTIR, and single-crystal XRD. These anthracene derivatives are able to recognize picric acid (2,4,6-trinitrophenol, PA) selectively down to parts per billion (ppb) level in aqueous as well as nonaqueous medium. Fluorescence emission of these derivatives in solution is significantly quenched by adding trace amounts of PA, even in the presence of other competing analogues, such as 2,4-dinitrophenol (2,4-DNP), 4-nitrophenol (NP), nitrobenzene (NB), benzoic acid (BA), and phenol (PH). The high sensitivity of these derivatives toward PA is considered as a combined effect of the proton-induced intramolecular charge transfer (ICT) as well as electron transfer from the electron-rich anthracene to the electron-deficient PA. Moreover, visual detection of PA has been successfully demonstrated in the solid state by using different substrates. Explosive chemistry! Anthracene derivatives are able to recognize picric acid (PA) selectively down to the parts per billion (ppb) level in aqueous as well as nonaqueous medium. Importantly, visual detection of PA has been successfully demonstrated in the solid state using different substrates (see figure).
2,6-Bis[4-(p-dihexylaminostyryl)-styryl]anthracene derivatives with large two-photon cross sections
Lee, Seung Kyu,Yang, Wen Jun,Choi, Jin Joo,Kim, Chang Ho,Jeon, Seung-Joon,Cho, Bong Rae
, p. 323 - 326 (2005)
(Chemical Equation Presented) Anthracene derivatives with a variety of donor-acceptor substituents have been synthesized and shown to exhibit large two-photon cross sections over a wide range of wavelengths.
Synthesis of poly(anthra-9,10-quinone-2,6-diyl)
Power, Gerald,Hodge, Philip,Clarke, Ian D.,Rabjohns, Michael A.,Goodbody, Ian
, p. 873 - 874 (1998)
The synthesis, via a precursor polymer, of poly(anthra-9,10-quinone-2,6-diyl) 1 is described and some of its properties are reported.
