共查询到20条相似文献,搜索用时 31 毫秒
1.
Thomas Wiesner Dr. Zhu Wu Dr. Jie Han Prof. Dr. Lei Ji Dr. Alexandra Friedrich Dr. Ivo Krummenacher Michael Moos Prof. Dr. Christoph Lambert Prof. Dr. Holger Braunschweig Benjamin Rudin Dr. Hilmar Reiss Olena Tverskoy Dr. Frank Rominger Prof. Dr. Andreas Dreuw Prof. Dr. Todd B. Marder Dr. Jan Freudenberg Prof. Dr. Uwe H. F. Bunz 《Chemistry (Weinheim an der Bergstrasse, Germany)》2022,28(69):e202201919
Tetraiodotetraazapentacene I4TAP , the last missing derivative in the series of halogenated silylated tetraazapentacenes, was synthesized via condensation chemistry from a TIPS-ethynylated diaminobenzothiadiazol in three steps. Single and double reduction furnished its air-stable monoanion and relatively air-stable dianion, both of which were characterized by crystallography. All three species are structurally and spectroscopically compared to non-halogenated TAP and Br4TAP . I4TAP is an n-channel material in thin-film transistors with average electron mobilities exceeding 1 cm2 (Vs)−1. 相似文献
2.
Thomas Wiesner Marcel Pardon Steffen Maier Dr. Frank Rominger Dr. Jan Freudenberg Prof. Dr. Uwe H. F. Bunz 《Chemistry (Weinheim an der Bergstrasse, Germany)》2022,28(69):e202201916
Four N-acenoacenes were synthesized and analyzed for their optoelectronic properties and solid-state packings. Two of the regioisomeric acridinoacridines are TIPS-ethynylated, whereas the other pair are Boc- and triflate substituted derivatives. The two TIPS-ethynyldiazaacenoacenes were processed into organic thin-film transistors with saturation hole mobilities reaching 2.9×10−2 cm2(Vs)−1. 相似文献
3.
Steffen Maier Robin Heckershoff Nikolai Hippchen Kerstin Brödner Dr. Frank Rominger Dr. Jan Freudenberg Prof. A. Stephen K. Hashmi Prof. Uwe H. F. Bunz 《Chemistry (Weinheim an der Bergstrasse, Germany)》2022,28(64):e202201842
Brominated pentannulated dihydrotetraazapentacenes were prepared by gold- or palladium-catalyzed 5-endo-dig cyclization of TIPS-ethynylated dihydrotetraazaacenes (TIPS = triisopropylsilyl). Post-functionalization was demonstrated by Sonogashira alkynylation and Rosenmund-von Braun cyanation. Calculations predict these species to act as n-type semiconductors, which was verified for two derivates through characterization in organic field-effect transistors. 相似文献
4.
Lukas Ahrens Steffen Maier Erik Misselwitz Dr. Thomas Oeser Dr. Frank Rominger Dr. Jan Freudenberg Prof. Dr. Uwe H. F. Bunz 《Chemistry (Weinheim an der Bergstrasse, Germany)》2021,27(41):10569-10573
The synthesis of two diazabisacenes is reported. A bisboronated naphthalene was Suzuki-coupled to substituted ethyl nicotinates, then cyclized by intramolecular Friedel-Crafts acylation. The resulting diketones were alkynylated and reduced to give the title compounds, bis(TIPS-ethynyl)-substituted naphtha[1,8-gh:5,4-g′h′]diquinoline and naphtho[1,8-bc:5,4-b′c′]diacridine. Nitrogen incorporation stabilizes the bisacenes with respect to oxidation compared to their consanguine nonaza analogs. 相似文献
5.
Dr. Karlee P. Castro Dr. Tyler T. Clikeman Nicholas J. DeWeerd Dr. Eric V. Bukovsky Kerry C. Rippy Dr. Igor V. Kuvychko Dr. Gao‐Lei Hou Dr. Yu‐Sheng Chen Dr. Xue‐Bin Wang Dr. Steven H. Strauss Dr. Olga V. Boltalina 《Chemistry (Weinheim an der Bergstrasse, Germany)》2016,22(12):3930-3936
In a simple, one‐step direct trifluoromethylation of phenazine with CF3I we prepared and characterized nine (poly)trifluoromethyl derivatives with up to six CF3 groups. The electrochemical reduction potentials and gas‐phase electron affinities show a direct, strict linear relation to the number of CF3 groups, with phenazine(CF3)6 reaching a record‐high electron affinity of 3.24 eV among perfluoroalkylated polyaromatics. 相似文献
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Yang Min Dr. Chuandong Dou Prof. Hongkun Tian Prof. Jun Liu Prof. Lixiang Wang 《Chemistry (Weinheim an der Bergstrasse, Germany)》2021,27(13):4364-4372
The B←N unit has a large dipole and it is isoelectronic to C−C moiety with no dipole. Incorporating B←N units into π-conjugated system is a powerful strategy to design organic small molecules and polymers with intriguing opto-electronic properties and excellent opto-electronic device performance. However, it is unclear how the B←N unit affects electronic structures and opto-electronic properties of large π-conjugated molecules. In this work, to address this question, we developed three dibenzo-azaacene molecules in which two B←N units were introduced at different positions. Although the dibenzo-azaacene skeleton is fully π-conjugated, the effect of B←N unit on the electronic structures of the adjacent rings is much stronger than that of the distant rings. As a result, the three molecules with isomerized B←N incorporation patterns possess different electronic structures and exhibit tunable opto-electronic properties. Among the three molecules, the centrosymmetrical molecule exhibits higher LUMO/HOMO energy levels than those of the two axisymmetrical molecules. When used as the active layer in organic field-effect transistors (OFETs), while the two axisymmetrical molecules show unipolar electron transporting property, the centrosymmetrical molecule exhibits ambipolar hole and electron transporting behavior. This work not only deepens our understanding on organoboron π-conjugated molecules, but also indicates a new strategy to tune opto-electronic properties of organic semiconductors for excellent device performance. 相似文献
8.
M. Sc. Lukas Ahrens Dr. Sebastian Hahn Dr. Frank Rominger Dr. Jan Freudenberg Prof. Uwe H. F. Bunz 《Chemistry (Weinheim an der Bergstrasse, Germany)》2019,25(64):14522-14526
The syntheses of new, fourfold alkynylated tetraazaacenoacenes (tetraazaanthracenoanthracene, tetraazatetracenotetracene and tetraazapentacenopentacene) are reported. This novel heteroacenoacene motif exhibits surprisingly strong electronic coupling between its constituting diazaacene units. 相似文献
9.
Lukas Ahrens Julian Butscher Victor Brosius Dr. Frank Rominger Dr. Jan Freudenberg Prof. Yana Vaynzof Prof. Uwe H. F. Bunz 《Chemistry (Weinheim an der Bergstrasse, Germany)》2020,26(2):412-418
The synthesis of five spiro-linked azaacene dimers is reported and their properties are compared to that of their monomers. Dimerization quenches emission of the longer (≥(hetero)tetracenes) derivatives and furnishes amorphous thin-films, the absorption is not affected. The larger derivatives were tested as acceptors in bulk-heterojunction photovoltaic devices with a maximum power conversion efficiency of up to 1.6 %. 相似文献
10.
Hilmar Reiss Dr. Lei Ji Jie Han Silke Koser Olena Tverskoy Dr. Jan Freudenberg Dr. Felix Hinkel Michael Moos Dr. Alexandra Friedrich Dr. Ivo Krummenacher Prof. Christoph Lambert Prof. Holger Braunschweig Prof. Andreas Dreuw Prof. Todd B. Marder Prof. Uwe H. F. Bunz 《Angewandte Chemie (International ed. in English)》2018,57(30):9543-9547
A cyclocondensation of TIPS‐ethynyl‐substituted diaminoarenes with in situ obtained 4,5‐dibromocyclohexa‐3,5‐diene‐1,2‐dione has led to the synthesis of tetrabromotetraazapentacene (BrTAP). BrTAP is easily reduced to its air‐stable radical anion and electron mobilities >0.56 cm2 V?1 s?1 can be achieved in thin‐film transistors. 相似文献
11.
Full Characterization and Photoelectrochemical Behavior of Pyrene‐fused Octaazadecacene and Tetraazaoctacene 下载免费PDF全文
Zilong Wang Jianwei Miao Dr. Guankui Long Dr. Peiyang Gu Dr. Junbo Li Prof. Dr. Naoki Aratani Prof. Dr. Hiroko Yamada Prof. Dr. Bin Liu Prof. Dr. Qichun Zhang 《化学:亚洲杂志》2016,11(4):482-485
The preparation of large azaacenes is very important because of their great potential in organic electronics. In this report, we successfully synthesized and fully characterized two stable pyrene‐fused large azaacenes: octaazadecacene and tetraazaoctacene through employing a relatively moderate aromatic unit pyrene as imbedded species in the backbone of azaacenes to ensure large conjugation and stability. The photoelectrochemical (PEC) studies indicate that both azaacenes display n‐type semiconductor behavior. 相似文献
12.
Dr. Mingliang Li Dr. Xiaoge Wang Guozhi Wang Shizhao Ren Shuo Li Prof. Feng Wei Prof. Shouke Yan Prof. Xuefeng Guo Prof. Hailing Tu 《Chemphyschem》2020,21(2):181-186
Organic semiconductor (OSC) crystals have great potential to be applied in many fields, as they can be flexibly designed according to the demands and show an outstanding device performance. However, OSCs with the capacity of solid-state crystallization (SSC) are developing too slowly to meet demands in productions and applications, due to their difficulties in molecular design and synthesis, unclear mechanism and high dependence on experimental conditions. In this work, in order to solve the problems, we synthesized an organic semiconductor capable of SSC at room temperature by adjusting the relationship between conjugated groups and functional groups. The thermodynamic and kinetic properties have been studied to discover the model of film SSC. Moreover, it can be purposefully controlled to prepare the high-quality crystals, and their corresponding organic electronic devices were further fabricated and discussed. 相似文献
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T. Suratwala Z. Gardlund K. Davidson D.R. Uhlmann S. Bonilla N. Peyghambarian 《Journal of Sol-Gel Science and Technology》1997,8(1-3):973-978
Numerous silylated coumarin dyes have been incorporated within silica : polydimethylsiloxane Polyceram hosts using the sol-gel process to form crack-free, polishable monoliths. The use of silylated laser dyes allows for covalently bonding the laser dyes to their hosts. Photostability of the samples was evaluated by measuring the decrease in the dye absorption in the Polyceram upon ultraviolet lamp exposure and by monitoring the fluorescence intensity as function of pump pulses from a N2 laser at 337 nm. Both methods showed a significant improvement in photo- and thermal-stability of the silylated dye Polyceram compared to that of the unsilylated dye Polyceram at a dye : Si mole ratio of 10-4 : 1. The improved stability is attributed to the immobilization and higher degree of caging of the silylated dye Polyceram with respect to the unsilylated dye Polyceram. 相似文献
15.
I. Antonyshyn F. R. Wagner M. Bobnar O. Sichevych U. Burkhardt M. Schmidt M. Knig K. Poeppelmeier A. P. Mackenzie E. Svanidze Yu. Grin 《Angewandte Chemie (International ed. in English)》2020,59(27):11136-11141
An efficient application of a material is only possible if we know its physical and chemical properties, which is frequently obstructed by the presence of micro‐ or macroscopic inclusions of secondary phases. While sometimes a sophisticated synthesis route can address this issue, often obtaining pure material is not possible. One example is TaGeIr, which has highly sample‐dependent properties resulting from the presence of several impurity phases, which influence electronic transport in the material. The effect of these minority phases was avoided by manufacturing, with the help of focused‐ion‐beam, a μm‐scale device containing only one phase—TaGeIr. This work provides evidence for intrinsic semiconducting behavior of TaGeIr and serves as an example of selective single‐domain device manufacturing. This approach gives a unique access to the properties of compounds that cannot be synthesized in single‐phase form, sparing costly and time‐consuming synthesis efforts. 相似文献
16.
《Angewandte Chemie (International ed. in English)》2017,56(43):13470-13474
The regioselective transformation of heterobuckybowl trichalcogenasumanenes 1 a , b at peripheral butoxy groups afforded trichalcogenasumanene ortho ‐quinones 2 a , b . Compounds 2 a , b are distinct from 1 a , b in terms of their molecular geometry and electronic state; that is, they have a shallower bowl depth and show absorbance in the NIR region. The reaction of 2 a , b with diamines resulted in a variety of heteropolycycles, including molecular spoon 3 a – 6 a , planar π‐systems 3 b – 6 b , and highly twisted [7‐6‐6]‐fused systems 7 a , b . These new heteropolycycles had different optical/electrical properties: 4 a,b showed hole mobility of approximately 0.002 cm2 V−1 s−1, 6 a displayed red emission in both solution and the solid state, and 7 a , b formed tight stacks of the curved π‐surface. 相似文献
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Dr. Ze-Hua Wu Dr. Hans Reichert Dr. Helmut Reichelt Prof. Dr. Thomas Basché Prof. Dr. Klaus Müllen 《Chemistry (Weinheim an der Bergstrasse, Germany)》2022,28(62):e202202291
A series of near-infrared (NIR) organic absorbers, named FNs and FPs , have been obtained with absorption maxima from 870 nm to 1100 nm and thus falling into the attractive second near-infrared region (NIR-II). The synthesis of their extended aromatic cores utilized an initial aryl-amination between 4-aminonaphthalene-1,8-dicarboximide ( NMI-NH2 ) or 9-aminoperylene-3,4-dicarboximide ( PMI-NH2 ) with chloro-substituted 9,10-anthraquinones followed by a novel base-induced cyclodehydrogenation. A NIR-II pigment, compound FPP , was obtained through de-alkylation of a soluble precursor. The synthesis of this photostable pigment is high-yielding and avoids column chromatographic purification which is important for many applications. 相似文献
19.
Processing and Photostability of Pyrromethene 567 Polycerams 总被引:1,自引:0,他引:1
T. Suratwala Z. Gardlund K. Davidson D.R. Uhlmann S. Bonilla N. Peyghambarian 《Journal of Sol-Gel Science and Technology》1997,8(1-3):953-958
Polyceram materials are attractive hosts for laser dyes because they can have high optical transparencies, high laser damage
thresholds, and the ability to tailor optical properties by varying the composition and synthetic routes. Pyrromethene 567
has been successfully incorporated within silica: polydimethylsiloxane (PDMS) Polycerams to obtain polishable, crack-free,
transparent monoliths using the sol-gel process. Fluorescence photostability was measured by pumping with aQ-switched, frequency doubled Nd: YAG laser (532 nm) at a pulse rate of 10 Hz. Fluorescence intensity dropped to 50% after
approximately 50,000 pulses at a fluence of 0.10 J/cm2. UV degradation studies were performed on Polycerams with different polymer contents, and the absorption photostability is
related to the solubility and type of caging of the dye. 相似文献
20.
To obtain solid‐state emissive materials having stimuli‐responsive luminescent chromic properties without phase transition, benzobithiophenes modified with two o‐carborane units having various substituents in the adjacent phenyl ring in o‐carborane were designed and synthesized. Their emission colors were strongly affected not only by the substituents at the para‐position of the phenyl ring but also by molecular distribution in the solid state. In particular, the emission colors were changed by heating without crystal phase transition. It was proposed that their thermochromic properties were correlated not with isomerization but with the molecular motion at the distorted benzobithiophene moiety. 相似文献