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Jiliang Zhang, George F S Whitehead, Troy D Manning, David Stewart, Craig I Hiley, Michael J Pitcher, Susanna Jansat, Kosmas Prassides, Matthew J Rosseinsky
We present the synthesis and characterization of the K+ intercalated rubrene (C42 H28 ) phase, K2 Rubrene (K2 R) and identify the co-existence of amorphous and crystalline materials in samples where the crystalline component is phase pure. We suggest this is characteristic of many intercalated alkali metal-polyaromatic hydrocarbon (PAH) systems, including those for which superconductivity has been claimed. The systematic investigation of K-rubrene solid state reactions using both K and KH sources reveals complex competition between K intercalation and the decomposition of rubrene, producing three K-intercalated compounds, namely, K2 R, K(RR*), and Kx R' (where R* and R' are rubrene decomposition derivatives C42 H26 and C30 H20 , respectively)...
November 30, 2018: Journal of the American Chemical Society
Kei Kitamura, Kenta Asahina, Yusaku Nagai, Keshu Zhang, Shogo Nomura, Katsunori Tanaka, Toshiyuki Hamura
A new synthetic route to 5,6,11,12-tetrakis(arylethynyl)tetracenes, π-extended rubrenes, was developed via [4 + 2] cycloadditions of dialkynylisobenzofuran and 1,4-naphthoquinone. Introduction of arylethynyl groups by double nucleophilic additions to tetracenequinone gave sterically congested (arylethynyl)tetracenes after reductive aromatization. The photophysical properties of the newly prepared π-conjugated molecules are also evaluated.
November 21, 2018: Organic & Biomolecular Chemistry
Marco J Pereira, Micaela Matta, Lionel Hirsch, Isabelle Dufour, Alejandro Briseno, Sai Manoj Gali, Yoann Olivier, Luca Muccioli, Alfred Crosby, Cédric Ayela, Guillaume Wantz
Micro-electromechanical systems (MEMS) made of organic materials have attracted efforts for the development a new generation of physical, chemical, and biological sensors, for which the electromechanical sensitivity is the current major concern. Here, we present an organic MEMS made of a rubrene single-crystal air-gap transistor. Applying mechanical pressure on the semiconductor results in high variations in drain current: an unparalleled gauge factor above 4000 has been measured experimentally. Such a high sensitivity is induced by the modulation of charge injection at the interface between the gold electrode and the rubrene semiconductor as an unusual transducing effect...
November 16, 2018: ACS Applied Materials & Interfaces
Shan-Shan Yang, Ming-Hui Jiang, Yaqin Chai, Ruo Yuan, Ying Zhuo
The accurate and rapid quantitative detection of antibodies had a significant influence in controlling and preventing diseases or toxins outbreaks. In this work, we first introduce the antibody-powered triplex-DNA nanomachine to release cargo DNA as substitute target for sensitive electrochemiluminescence (ECL) detection of anti-digoxigenin based on a novel ternary ECL system. It is worth noting that the cargo DNA as a substitute target of antibody can further participate in an enzyme-assisted cycling strand displacement reaction (CSDR) to achieve ECL signal amplification and improve the sensitivity of antibody detection...
October 11, 2018: ACS Applied Materials & Interfaces
Yusuke Wakabayashi, Masanari Nakamura, Kaori Sasaki, Takahiro Maeda, Yuutaro Kishi, Hiroyuki Ishii, Nobuhiko Kobayashi, Susumu Yanagisawa, Yuma Shimo, Yoshihiro Kubozono
Surface structure relaxation of organic semiconductors affects the properties of organic devices, although such relaxation has not been well explored. Only two examples have been experimentally reported; tetracene shows a large surface relaxation, while rubrene exhibits no relaxation. Therefore, a systematic investigation of the surface relaxation is conducted on [ n]phenacenes ( n = 5, 7, and 9). Electron density analyses are performed based on the synchrotron surface X-ray scattering with the aid of first-principles calculations...
October 31, 2018: Journal of the American Chemical Society
Chaojun Li, Xiaofeng Liu, Jianrong Qiu
Organic semiconductors, such as polycyclic aromatic hydrocarbons, are typically not responsive to near infrared (NIR) light due to their relatively large bandgaps. Here, we show that the NIR light at 980 nm can be efficiently converted to broadband visible upconversion (UC) emission by rubrene molecules in a solution dispersed with upconversion nanoparticles (UCNPs). Spectroscopic characterizations indicate that the sensitization of emission by rubrene molecules strongly depends on the location of the 4f levels of Er3+ ions and the interplay between reabsorption and Förster-type energy transfer...
November 7, 2018: Physical Chemistry Chemical Physics: PCCP
Shumei Li, Xu Li, Lizhong Wang, Hongbo Liu
A white organic light emitting device with structure of ITO/2T-NATA(20)/NPBX(15)/DPVBi(15)/ Alq:Rub(10, x)/Alq3(40)/LiF/Al was fabricated using doping rubrene. When the concentration of rubrene is 3 wt.%, the chromaticity is the best (0.319, 0.317), and the color coordinates are stable. When the thickness of the doping layer is 20 nm, the efficiency and luminance of the devices are the highest, which are 5.1022 cd/A and 17130 cd/m2, respectively. On the basis, a test system is consisted of Solomon's OLED display control driver chip SSD1306 and microcontroller AT89C52, which tests the OLED dot matrix through the program to determine whether the matrix has dead point...
December 1, 2018: Journal of Nanoscience and Nanotechnology
Cheol-Joon Park, Hyeon Jung Park, Jae Yoon Lee, Jeongyong Kim, Chul-Ho Lee, Jinsoo Joo
A several-layer n-type MoS2 was partially hybridized with an organic crystalline p-type rubrene nanosheet through van der Waals interactions to fabricate a two-dimensional (2-D) lateral-type n-p heterojunction optoelectronic device. The field-effect transistors (FETs) using lateral-type MoS2 /rubrene hybrids exhibited both gate-tunable diode and anti-ambipolar transistor characteristics. The FET devices show the coexistence of n-type states, p-type states, and off-states controlled by the gate bias. From the photocurrent mapping experiments, the gate-bias-dependent photovoltaic effect was observed from the heterojunction regions of the MoS2 /rubrene FETs...
September 5, 2018: ACS Applied Materials & Interfaces
Xinglong Ren, C Daniel Frisbie, Chris Leighton
Although electrolyte gating has been demonstrated to enable control of electronic phase transitions in many materials, long sought-after gate-induced insulator-metal transitions in organic semiconductors remain elusive. To better understand limiting factors in this regard, here we report detailed wide-range resistance-temperature ( R- T) measurements at multiple gate voltages on ionic-liquid-gated rubrene single crystals. Focusing on the previously observed high-bias regime where conductance anomalously decreases with increasing bias magnitude, we uncover two surprising (and related) features...
September 6, 2018: Journal of Physical Chemistry Letters
Jae Joon Kim, Stefan Bachevillier, D Leonardo Gonzalez Arellano, Benjamin P Cherniawski, Edmund K Burnett, Natalie Stingelin, Cédric Ayela, Özlem Usluer, Stefan C B Mannsfeld, Guillaume Wantz, Alejandro L Briseno
The relationship between charge transport and surface morphology is investigated by utilizing rubrene single crystals of varying thicknesses. In the case of pristine crystals, the surface conductivities decrease exponentially as the crystal thickness increases until ∼4 μm, beyond which the surface conductivity saturates. Investigation of the surface morphology using optical and atomic force microscopy reveals that thicker crystals have a higher number of molecular steps, increasing the overall surface roughness compared with thin crystals...
August 8, 2018: ACS Applied Materials & Interfaces
Ryo Nagata, Hajime Nakanotani, William J Potscavage, Chihaya Adachi
Harvesting of both triplets and singlets yields electroluminescence quantum efficiencies of nearly 100% in organic light-emitting diodes (OLEDs), but the production efficiency of excitons that can undergo radiative decay is theoretically limited to 100% of the electron-hole pairs. Here, breaking of this limit by exploiting singlet fission in an OLED is reported. Based on the dependence of electroluminescence intensity on an applied magnetic field, it is confirmed that triplets produced by singlet fission in a rubrene host matrix are emitted as near-infrared (NIR) electroluminescence by erbium(III) tris(8-hydroxyquinoline) (ErQ3 ) after excitonic energy transfer from the "dark" triplet state of rubrene to an "emissive" state of ErQ3 , leading to NIR electroluminescence with an overall exciton production efficiency of 100...
July 5, 2018: Advanced Materials
T Mukherjee, Sumona Sinha, M Mukherjee
X-ray absorption spectra (XAS), the density of states (DOS) and the electron density distribution of the HOMO and LUMO for flat and twisted rubrene molecules have been calculated using density functional theory (DFT). The simulated XAS spectra are validated by experimental C K-edge near-edge X-ray absorption fine structure (NEXAFS) data. We demonstrate that the NEXAFS spectra of rubrene thin films of different thicknesses can be explained in terms of different combinations of spectral intensity from the twisted and the flat randomly oriented molecules...
July 11, 2018: Physical Chemistry Chemical Physics: PCCP
Dong Wei, Fusheng Ma, Rui Wang, Shangyi Dou, Peng Cui, Hao Huang, Jun Ji, Endong Jia, Xiaojie Jia, Sajid Sajid, Ahmed Mourtada Elseman, Lihua Chu, Yingfeng Li, Bing Jiang, Juan Qiao, Yongbo Yuan, Meicheng Li
Migration of ions can lead to photoinduced phase separation, degradation, and current-voltage hysteresis in perovskite solar cells (PSCs), and has become a serious drawback for the organic-inorganic hybrid perovskite materials (OIPs). Here, the inhibition of ion migration is realized by the supramolecular cation-π interaction between aromatic rubrene and organic cations in OIPs. The energy of the cation-π interaction between rubrene and perovskite is found to be as strong as 1.5 eV, which is enough to immobilize the organic cations in OIPs; this will thus will lead to the obvious reduction of defects in perovskite films and outstanding stability in devices...
August 2018: Advanced Materials
Takashi Yamada, Mariko Kinoshita, Kento Araragi, Yu Watanabe, Takahiro Ueba, Hiroyuki S Kato, Toshiaki Munakata
Spectroscopic and nanoscale imaging investigations concerning the spatial extent of molecular orbitals at organic/substrate interfaces have been of intense interest to understand charge dynamics. Here, the spatial extent of unoccupied molecular orbitals of ultrathin rubrene [5,6,11,12-tetraphenyltetracene] films has been investigated with scanning tunneling microscopy and spectroscopy. Based on constant-current distance (z)-voltage (V) measurements, the unoccupied energy levels are elucidated and found to be consistent with previously reported macroscopic two-photon photoemission (2PPE) spectroscopy...
June 27, 2018: Physical Chemistry Chemical Physics: PCCP
Lu Zhang, Kok Wai Cheah
Thermally activated delayed florescence (TADF) materials can be an efficient host in organic LED (OLED). It is because it is possible to couple energetically the emission energy level of a dopant to the energy levels in the TADF material. In this work fluorescent emitters 2,3,6,7-tetrahydro-1,1,7,7,-tetramethyl-1H,5 H,11H-10-(2-benzothiazolyl)quinolizino-9,9a,1gh coumarin (c545t) and 5,6,11,12-tetraphenyltetracene (rubrene) were used as dopants in a blended TADF host; tris(4-carbazoyl-9-ylphenyl)amine (TCTA) with 2,4,6-tris(3'-(pyridin-3-yl)biphenyl-3-yl)-1,3,5-triazine (Tm3PyBPZ)...
June 11, 2018: Scientific Reports
Gaozhan Xie, Sebastian Hahn, Frank Rominger, Jan Freudenberg, Uwe H F Bunz
The synthesis, properties and solid state X-ray single crystal structures of two new rubrene-derivatives, viz diazarubrene (4,4'-(6,12-diphenyltetracene-5,11-diyl)dipyridine) and tetraazarubrene (5,6,11,12-tetra(pyridin-4-yl)tetracene), are reported. Both the azarubrenes are more oxidatively stable than rubrene itself and show very similar optical properties but differ in their crystal packing from that of rubrene.
July 5, 2018: Chemical Communications: Chem Comm
Xiaoyu Xie, Alejandro Santana-Bonilla, Alessandro Troisi
A substantial amount of evidence indicates a relevant role played by the nonlocal electron-phonon couplings in the mechanism of charge transport in organic semiconductors. In this work, we compute the nonlocal electron-phonon coupling for the prototypical molecular semiconductors rubrene and tetracene using the phonon modes obtained from ab initio methods. We do not make the rigid molecular approximation allowing a mixing of intra- and intermolecular modes, and we use a supercell approach to sample the momentum space...
July 10, 2018: Journal of Chemical Theory and Computation
Yuanyuan Hu, Lang Jiang, Qinjun Chen, Jing Guo, Zhuojun Chen
It is commonly accepted that gate dielectric dipoles can induce energetic disorder in organic field-effect transistors. However, convincing experimental evidence that directly demonstrate this effect are still in lack. In this work, we present a combined experimental and theoretical study to reveal this effect. We have investigated the temperature-dependent mobility of two rubrene single-crystal transistors with different polymer dielectrics. Model fittings of the data indicate there is higher energetic disorder in the device on dielectric with larger permittivity...
June 7, 2018: Journal of Physical Chemistry Letters
Yasuyuki Yokota, Hiroo Miyamoto, Akihito Imanishi, Jun Takeya, Kouji Inagaki, Yoshitada Morikawa, Ken-Ichi Fukui
Electric double-layer transistors based on ionic liquid/organic semiconductor interfaces have been extensively studied during the past decade because of their high carrier densities at low operation voltages. Microscopic structures and the dynamics of ionic liquids likely determine the device performance; however, knowledge of these is limited by a lack of appropriate experimental tools. In this study, we investigated ionic liquid/organic semiconductor interfaces using molecular dynamics to reveal the microscopic properties of ionic liquids...
May 9, 2018: Physical Chemistry Chemical Physics: PCCP
Yujeong Lee, Kang Lib Kim, Han Sol Kang, Beomjin Jeong, Chanho Park, Insung Bae, Seok Ju Kang, Youn Jung Park, Cheolmin Park
Epitaxial crystallization of thin poly(vinylidene fluoride-co-trifluoroethylene) (PVDF-TrFE) films is important for the full utilization of their ferroelectric properties. Epitaxy can offer a route for maximizing the degree of crystallinity with the effective orientation of the crystals with respect to the electric field. Despite various approaches for the epitaxial control of the crystalline structure of PVDF-TrFE, its epitaxy on a semiconductor is yet to be accomplished. Herein, the epitaxial growth of PVDF-TrFE crystals on a single-crystalline organic semiconductor rubrene grown via physical vapor deposition is presented...
May 2018: Small
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