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.
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.
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.
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.
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 and photophysical properties of multilayer emitting π-p-π fluorophores
Wang, Xiaorong,Zhao, Sanxiao,Chen, Yin,Wang, Jingang
, (2020)
Fluorescence is widely used in biology, medicine, and analytical chemistry. The anthracene framework has received considerable attention for the luminescent molecular design as an attractive building unit. Herein, Luminescent “π-p-π” anthracene crystals with different multilayer stacking modes were conducted by experimental methods and theoretical calculations. It was found that “these anthracene derivatives showed strong fluorescence and stability in both solution and solid-state; A face-to-face π-π stacking arrangement dominated in N9,N10-diphenyl-2,6-bis((trimethylsilyl)ethynyl)anthracene-9,10-diamine (4), while C/N–H … π interactions were observed in the crystal lattice of 2,6-diethynyl-N9,N10-diphenylanthracene-9,10-diamine (5); The excitation processes of S0→S1 of 4 and 5 belonged to Localized Excitation; The number of photons emitted could be nearly equal to the number of photons absorbed below 120K”. This study is expected to assist in the design of photonic materials in the field of optical chemistry.
Two-Terminal Molecular Memory through Reversible Switching of Quantum Interference Features in Tunneling Junctions
Carlotti, Marco,Soni, Saurabh,Kumar, Sumit,Ai, Yong,Sauter, Eric,Zharnikov, Michael,Chiechi, Ryan C.
, p. 15681 - 15685 (2018/11/06)
Large-area molecular tunneling junctions comprising self-assembled monolayers of redox-active molecules are described that exhibit two-terminal bias switching. The as-prepared monolayers undergo partial charge transfer to the underlying metal substrate (Au, Pt, or Ag), which converts their cores from a quinoid to a hydroquinoid form. The resulting rearomatization converts the bond topology from a cross-conjugated to a linearly conjugated π system. The cross-conjugated form correlates to the appearance of an interference feature in the transmission spectrum that vanishes for the linearly conjugated form. Owing to the presence of electron-withdrawing nitrile groups, the reduction potential and the interference feature lie close to the work function and Fermi level of the metallic substrate. We exploited the relationship between conjugation patterns and quantum interference to create nonvolatile memory in proto-devices using eutectic Ga–In as the top contact.
