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1.
Gaobo Lin Lingna Wang Yizhou Yang Zitong Liu Guanxin Zhang Deqing Zhang 《化学:亚洲杂志》2019,14(10):1712-1716
Conjugated molecules with low lying LUMO levels are demanding for the development of air stable n‐type organic semiconductors. In this paper, we report a new A‐D‐A′‐D‐A conjugated molecule ( DAPDCV ) entailing diazapentalene (DAP) and dicyanovinylene groups as electron accepting units. Both theoretical and electrochemical studies manifest that the incorporation of DAP unit in the conjugated molecule can effectively lower the LUMO energy level. Accordingly, thin film of DAPDCV shows n‐type semiconducting behavior with electron mobility up to 0.16 cm2?V?1?s?1 after thermal annealing under N2 atmosphere. Moreover, thin film of DAPDCV also shows stable n‐type transporting property in air with mobility reaching 0.078 cm2?V?1?s?1. 相似文献
2.
Konstantin Karaghiosoff Thomas M. Klaptke Alexej Michailovski Gerhard Holl 《Acta Crystallographica. Section C, Structural Chemistry》2002,58(9):o580-o581
The title compound (systematic name: 4,10‐dinitro‐2,6,8,12‐tetraoxa‐4,10‐diazatetracyclo[5.5.0.03,11.05,9]dodecane), C6H6N4O8, exhibits the highest density among known N‐nitramines, due to its close‐packed crystal structure. It may be regarded as consisting of a distorted hexagonal close‐packed lattice formed by the isowurtzitane cages, with the nitro groups occupying the free space between the cages. 相似文献
3.
Air‐tolerant Fabrication and Enhanced Thermoelectric Performance of n‐Type Single‐walled Carbon Nanotubes Encapsulating 1,1′‐Bis(diphenylphosphino)ferrocene 下载免费PDF全文
Prof. Yoshiyuki Nonoguchi Yu Iihara Kenji Ohashi Tomoko Murayama Prof. Tsuyoshi Kawai 《化学:亚洲杂志》2016,11(17):2423-2427
The thermally‐triggered n‐type doping of single‐walled carbon nanotubes is demonstrated using 1,1′‐bis(diphenylphosphino)ferrocene, a novel n‐type dopant. Through a simple thermal vacuum process, the phosphine compounds are moderately encapsulated inside single‐walled carbon nanotubes. The encapsulation into SWNTs is carefully characterized using Raman/X‐ray spectroscopy and transmission electron microscopy. This easy‐to‐handle doping with air‐stable precursors for n‐type SWNTs enables the large‐scale fabrication of thermoelectric materials showing an excellent power factor exceeding approximately 240 μW mK?2. 相似文献
4.
Hong‐Gang Cheng Shuqing Chen Ruiming Chen Qianghui Zhou 《Angewandte Chemie (Weinheim an der Bergstrasse, Germany)》2019,131(18):5890-5902
The Catellani reaction is known as a powerful strategy for the expeditious synthesis of highly substituted arenes and benzo‐fused rings, which are usually difficult to access through traditional cross‐coupling strategies. It utilizes the synergistic interplay of palladium and norbornene catalysis to facilitate sequential ortho C?H functionalization and ipso termination of aryl halides in a single operation. In classical Catellani‐type reactions, aryl halides are mainly used as the substrates, and a Pd0 catalyst is required to initiate the reaction. Nevertheless, recent advances showcase that Catellani‐type reactions can also be initiated by a PdII catalyst with different starting materials instead of aryl halides via different reaction mechanisms and under different conditions. This emerging concept of PdII/norbornene cooperative catalysis has significantly advanced Catellani‐type reactions, thus enabling future developments of this field. In this Minireview, PdII‐initiated Catellani‐type reactions and their application in the synthesis of bioactive molecules are summarized. 相似文献
5.
A quinoidal small‐molecule semiconductor QDPPBTT was synthesized. Organic thin‐film transistor (OTFT) devices based on QDPPBTT showed an electron mobility as high as 0.13 cm2 V?1 s?1 and Ion/Ioff ratio of 106 under ambient conditions. We suggested that 2D extended π‐conjugation and quinoid‐enhancing effect had an important role in electron mobility and stability of n‐type FET devices, which might be a good strategy in designing new material systems. 相似文献
6.
Jie Zhou Xinxing Yin Zihao Dong Amjad Ali Zhaoning Song Niraj Shrestha Sandip Singh Bista Qinye Bao Randy J. Ellingson Yanfa Yan Weihua Tang 《Angewandte Chemie (Weinheim an der Bergstrasse, Germany)》2019,131(39):13855-13859
Organic p‐type semiconductors with tunable structures offer great opportunities for hybrid perovskite solar cells (PVSCs). We report herein two dithieno[3,2‐b:2′,3′‐d]pyrrole (DTP) cored molecular semiconductors prepared through π‐conjugation extension and an N‐alkylation strategy. The as‐prepared conjugated molecules exhibit a highest occupied molecular orbital (HOMO) level of ?4.82 eV and a hole mobility up to 2.16×10?4 cm2 V?1 s?1. Together with excellent film‐forming and over 99 % photoluminescence quenching efficiency on perovskite, the DTP based semiconductors work efficiently as hole‐transporting materials (HTMs) for n‐i‐p structured PVSCs. Their dopant‐free MA0.7FA0.3PbI2.85Br0.15 devices exhibit a power conversion efficiency over 20 %, representing one of the highest values for un‐doped molecular HTMs based PVSCs. This work demonstrates the great potential of using a DTP core in designing efficient semiconductors for dopant‐free PVSCs. 相似文献
7.
A series of electronegative π‐conjugated compounds composed of carbonyl‐bridged bithiazole and alkyl‐substituted dioxocyclopenta[b]thiophene were synthesized as a candidate for solution‐processable n‐type organic semiconductor materials and characterized on the basis of photophysical and electrochemical properties. Cyclic voltammetry measurements showed that the first half‐wave reduction potentials of these compounds are between −0.97 and −1.14 V versus ferrocene/ferrocenium, which corresponds to lowest unoccupied molecular orbital energy levels between −3.83 and −3.66 eV. Thanks to hexyl or dodecyl groups in the molecules, the compounds are sufficiently soluble to realize the fabrication of their thin films through a spin‐coating method. As a result, the prepared organic field‐effect transistors based on these newly developed compounds exhibited n‐channel characteristics not only under vacuum but also in air, and the best field‐effect electron mobility observed under vacuum was 0.011 cm2 V−1 s−1 with an on/off ratio of 108 and a threshold voltage of 16 V. 相似文献
8.
Yang Min Dr. Chuandong Dou Dr. Hongkun Tian Prof. Yanhou Geng Prof. Jun Liu Prof. Lixiang Wang 《Angewandte Chemie (International ed. in English)》2018,57(7):2000-2004
We disclose a novel strategy to design n‐type acenes through the introduction of boron–nitrogen coordination bonds (B←N). We synthesized two azaacenes composed of two B←N units and six/eight linearly annelated rings. The B←N unit significantly perturbed the electronic structures of the azaacenes: Unique LUMOs delocalized over the entire acene skeletons and decreased aromaticity of the B←N‐adjacent rings. Most importantly, these B←N‐containing azaacenes exhibited low‐lying LUMO energy levels and high electron affinities, thus leading to n‐type character. The solution‐processed organic field‐effect transistor based on one such azaacene exhibited unipolar n‐type characteristics with an electron mobility of 0.21 cm2 V?1 s?1. 相似文献
9.
Solution‐Processable n‐Type Semiconductors Based on Unsymmetrical Naphthalene Imides: Synthesis,Characterization, and Applications in Field‐Effect Transistors 下载免费PDF全文
A series of unsymmetrical naphthalene imide derivatives ( 1a , 1b , 2 , 3 , 4 , 5 ) with high electron affinity was synthesized and used in n‐channel organic field‐effect transistors (OFETs). They have very good solubility in common organic solvents and good thermal stability up to 320 °C. Their photophysical, electrochemical, and thermal properties were investigated in detail. They showed low‐lying LUMO energy levels from ?3.90 to ?4.15 eV owing to a strong electron‐withdrawing character. Solution‐processed thin‐film OFETs based on 1a , 1b , 2 , 3 , 4 were measured in both N2 and air. They all showed n‐type FET behavior. The liquid‐crystalline compounds 1a , 1b , and 3 showed good performance owing to the self‐healing properties of the film in the liquid‐crystal phase. Compound 3 has an electron mobility of up to 0.016 cm2 V?1 s?1 and current on/off ratios of 104–105. 相似文献
10.
Incorporation of 2,6‐Connected Azulene Units into the Backbone of Conjugated Polymers: Towards High‐Performance Organic Optoelectronic Materials 下载免费PDF全文
Hanshen Xin Dr. Congwu Ge Dr. Xuechen Jiao Dr. Xiaodi Yang Kira Rundel Prof. Christopher R. McNeill Prof. Xike Gao 《Angewandte Chemie (International ed. in English)》2018,57(5):1322-1326
Azulene is a promising candidate for constructing optoelectronic materials. An effective strategy is presented to obtain high‐performance conjugated polymers by incorporating 2,6‐connected azulene units into the polymeric backbone, and two conjugated copolymers P(TBAzDI‐TPD) and P(TBAzDI‐TFB) were designed and synthesized based on this strategy. They are the first two examples for 2,6‐connected azulene‐based conjugated polymers and exhibit unipolar n‐type transistor performance with an electron mobility of up to 0.42 cm2 V?1 s?1, which is among the highest values for n‐type polymeric semiconductors in bottom‐gate top‐contact organic field‐effect transistors. Preliminary all‐polymer solar cell devices with P(TBAzDI‐TPD) as the electron acceptor and PTB7‐Th as the electron donor display a power conversion efficiency of 1.82 %. 相似文献
11.
Chengyuan Wang Jing Zhang Guankui Long Naoki Aratani Hiroko Yamada Yang Zhao Qichun Zhang 《Angewandte Chemie (Weinheim an der Bergstrasse, Germany)》2015,127(21):6390-6394
Increasing the length of N‐heteroacenes or their analogues is highly desirable because such materials could have great potential applications in organic electronics. In this report, the large π‐conjugated N‐heteroquinone 6,10,17,21‐tetra‐((triisopropylsilyl)ethynyl)‐5,7,9,11,16,18,20,22‐octaazanonacene‐8,19‐dione (OANQ) has been synthesized and characterized. The as‐prepared OANQ shows high stability under ambient conditions and has a particularly low LUMO level, which leads to it being a promising candidate for air‐stable n‐type field‐effect transistors (FETs). In fact, FET devices based on OANQ single crystals have been fabricated and an electron mobility of up to 0.2 cm2 V−1 s−1 under ambient conditions is reported. More importantly, no obvious degradation was observed even after one month. Theoretical calculations based on the single crystal are consistent with the measured mobility. 相似文献
12.
Synthesis,Structure, and Air‐stable N‐type Field‐Effect Transistor Behaviors of Functionalized Octaazanonacene‐8,19‐dione 下载免费PDF全文
Chengyuan Wang Dr. Jing Zhang Dr. Guankui Long Prof. Dr. Naoki Aratani Prof. Dr. Hiroko Yamada Prof. Dr. Yang Zhao Prof. Dr. Qichun Zhang 《Angewandte Chemie (International ed. in English)》2015,54(21):6292-6296
Increasing the length of N‐heteroacenes or their analogues is highly desirable because such materials could have great potential applications in organic electronics. In this report, the large π‐conjugated N‐heteroquinone 6,10,17,21‐tetra‐((triisopropylsilyl)ethynyl)‐5,7,9,11,16,18,20,22‐octaazanonacene‐8,19‐dione (OANQ) has been synthesized and characterized. The as‐prepared OANQ shows high stability under ambient conditions and has a particularly low LUMO level, which leads to it being a promising candidate for air‐stable n‐type field‐effect transistors (FETs). In fact, FET devices based on OANQ single crystals have been fabricated and an electron mobility of up to 0.2 cm2 V?1 s?1 under ambient conditions is reported. More importantly, no obvious degradation was observed even after one month. Theoretical calculations based on the single crystal are consistent with the measured mobility. 相似文献
13.
Day‐Shin Hsu Prof. Dr. Yu‐Yu Chou Yen‐Shih Tung Chun‐Chen Liao Prof. Dr. 《Chemistry (Weinheim an der Bergstrasse, Germany)》2010,16(10):3121-3131
An efficient and short entry to polyfunctionalized linear triquinanes from 2‐methoxyphenols is described by utilizing the following chemistry. The Diels–Alder reactions of masked o‐benzoquinones, derived from 2‐methoxyphenols, with cyclopentadiene afford tricyclo[5.2.2.02,6]undeca‐4,10‐dien‐8‐ones. Photochemical oxa‐di‐π‐methane (ODPM) rearrangements and 1,3‐acyl shifts of the Diels–Alder adducts are investigated. The ODPM‐rearranged products are further converted to linear triquinanes by using an O‐stannyl ketyl fragmentation. Application of this efficient strategy to the total synthesis of (±)‐Δ9(12)‐capnellene was accomplished from 2‐methoxy‐4‐methylphenol in nine steps with 20 % overall yield. 相似文献
14.
The effect of component contents and membrane thickness on the detection limit (DL), slope (m), linear range (LR) and response time (RT) of Pb2+ solid contact potentiometric ion selective electrodes (SCISE) based on 4,10‐diaza‐2,3,11,12‐dibenzo‐18‐crown‐6 (1), 4,10‐diaza‐2,3,11,12‐di(4‐tert‐butylbenzo)‐18‐crown‐6 (2) and 4,10‐diaza‐2,3,11,12‐dibenzo‐18‐crown‐6‐N,N′‐di(carboxymethyl) (3) as ionophores was studied by open circuit potential (OCP) and electrochemical impedance spectroscopy (EIS) measurements. The use of an intermediate layer of poly(3‐octyl)thiophene between the gold substrate and the selective membrane was explored. SCISE prepared showing the best responses had typical DL, m, LR and RT values of 10?6 M, 29 mV/dec, 10?5 to 10?3 M and 2 minutes. 相似文献
15.
Yang Lu Zi‐Di Yu Run‐Zhi Zhang Ze‐Fan Yao Hao‐Yang You Li Jiang Hio‐Ieng Un Bo‐Wei Dong Miao Xiong Jie‐Yu Wang Jian Pei 《Angewandte Chemie (Weinheim an der Bergstrasse, Germany)》2019,131(33):11512-11516
Low n‐doping efficiency and inferior stability restrict the thermoelectric performance of n‐type conjugated polymers, making their performance lag far behind of their p‐type counterparts. Reported here are two rigid coplanar poly(p‐phenylene vinylene) (PPV) derivatives, LPPV‐1 and LPPV‐2 , which show nearly torsion‐free backbones. The fused electron‐deficient rigid structures endow the derivatives with less conformational disorder and low‐lying lowest unoccupied molecular orbital (LUMO) levels, down to ?4.49 eV. After doping, two polymers exhibited high n‐doping efficiency and significantly improved air stability. LPPV‐1 exhibited a high conductivity of up to 1.1 S cm?1 and a power factor as high as 1.96 μW m?1 K?2. Importantly, the power factor of the doped LPPV‐1 thick film degraded only 2 % after 7 day exposure to air. This work demonstrates a new strategy for designing conjugated polymers, with planar backbones and low LUMO levels, towards high‐performance and potentially air‐stable n‐type polymer thermoelectrics. 相似文献
16.
Florian Schlütter Georges M. Pavlov Jean‐François Gohy Andreas Winter Andreas Wild Martin D. Hager Stephanie Hoeppener Ulrich S. Schubert 《Journal of polymer science. Part A, Polymer chemistry》2011,49(6):1396-1408
A series of RuII heterodinuclear complexes of ABA ‐type with electron‐deficient bis‐terpyridines as building blocks was synthesized by (R‐tpy)RuIIICl3 complexation. These compounds were characterized by NMR spectroscopy, MALDI‐TOF, ESI‐TOF mass spectrometry, and elemental analysis. The results were compared with a coil‐rod‐coil RuII metallo‐supramolecular copolymer, which was synthesized by bis‐complex formation between a hydrophilic ω‐terpyridine poly(ethylene glycol) RuII mono‐complex and a hydrophobic bis‐terpyridine‐functionalized rigid core. This amphiphilic RuII triblock copolymer showed self‐assembly to clusters and micelles in aqueous solution, which was studied by transmission electron microscopy and dynamic light scattering. Applying velocity sedimentation experiments the number of amphiphilic RuII ABA triblock copolymer molecules within the micelles could be estimated. Finally, the photophysical properties of the RuII supramolecular assemblies were investigated by UV–vis spectroscopy. © 2011 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2011 相似文献
17.
Werner Andres Harald Günther Maria‐Eugenia Günther Heike Hausmann Günther Jikeli Henning vonPuttkamer Hans Schmickler Jier Niu‐Schwarz W.H.Eugen Schwarz 《Helvetica chimica acta》2001,84(6):1737-1755
The bonding situation in a series of biphenylene analogues – benzo[b]biphenylene and its dication, 4,10‐dibromobenzo[b]biphenylene, naphtho[2,3‐b]biphenylene and its dianion, benzo[a]biphenylene, (biphenylene)tricarbonylchromium, benzo[3,4]cyclobuta[1,2‐c]thiophene, benzo[3,4]cyclobuta[1,2‐c]thiophene 2‐oxide, benzo[3,4]cyclobuta[1,2‐c]thiophene 2,2‐dioxide, 4,10‐diazabenzo[b]biphenylene, biphenylene‐2,3‐dione, benzo[3,4]cyclobuta[1,2‐b]anthracene‐6,11‐dione, and 3,4‐dihydro‐2H‐benzo[3,4]cyclobuta[1,2]cycloheptene – where one of the two benzo rings of biphenylene is replaced by a different π‐system (B) was investigated on the basis of the NMR parameters of these systems. From the vicinal 1H,1H spin‐spin coupling constants, the electronic structure of the remaining benzo ring (A) is derived via the Q‐value method. It is found that increasing tendency of B to tolerate exocyclic double bonds at the central four‐membered ring of these systems favors increased π‐electron delocalization in the A ring. The analysis of the chemical shifts supports this conclusion. NICS (nucleus‐independent chemical shift) values as well as C,C bond lengths derived from ab initio calculations are in excellent agreement with the experimental data. The charged systems benzo[b]biphenylene dication and naphtho[2,3‐b]biphenylene dianion ( 7 2−) are also studied by 13C NMR measurements. The charge distribution found closely resembles the predictions of the simple HMO model and reveals that 7 2− can be regarded as a benzo[3,4]cyclobuta[1,2‐b]‐substituted anthracene dianion. It is shown that the orientation of the tricarbonylchromium group in complexes of benzenoid aromatics can be derived from the vicinal 1H,1H coupling constants. 相似文献
18.
Synthesis,Properties, and n‐Type Transistor Characteristics of π‐Conjugated Compounds Having a Carbonyl‐Bridged Thiazole‐Fused Polycyclic System 下载免费PDF全文
Prof. Yutaka Ie Chihiro Sato Dr. Masashi Nitani Prof. Hirokazu Tada Prof. Yoshio Aso 《Chemistry (Weinheim an der Bergstrasse, Germany)》2014,20(50):16509-16515
A series of electron‐deficient π‐conjugated systems with 4,9‐dihydro‐s‐indaceno[2,1‐d:6,5‐d′]dithiazole‐4,9‐dione‐based structures and fluorinated acyl groups as the terminal units have been designed and synthesized for application as organic field‐effect transistor (OFET) materials. The thermal, photophysical, and electrochemical properties and OFET performance of the synthesized compounds were investigated. OFET evaluation revealed that all compounds exhibited typical electron‐transporting characteristics, and electron mobilities up to 0.26 cm2 V?1 s?1 could be achieved. The air stabilities of OFET operation were dependent on the nature of the compounds and were investigated by X‐ray diffraction and atomic force microscopy. The terminal units had a great influence not only on the molecular properties, but also on the film‐forming properties and OFET performance. 相似文献
19.
Thieno[3,2‐b]thiophene‐Diketopyrrolopyrrole‐Based Quinoidal Small Molecules: Synthesis,Characterization, Redox Behavior,and n‐Channel Organic Field‐Effect Transistors 下载免费PDF全文
Chao Wang Yaping Zang Yunke Qin Qian Zhang Yuanhui Sun Dr. Chong‐an Di Prof. Wei Xu Prof. Daoben Zhu 《Chemistry (Weinheim an der Bergstrasse, Germany)》2014,20(42):13755-13761
We report the synthesis, characterization, redox behavior, and n‐channel organic field‐effect (OFET) characteristics of a new class of thieno[3,2‐b]thiophene‐diketopyrrolopyrrole‐based quinoidal small molecules 3 and 4 . Under ambient atmosphere, solution‐processed thin‐film transistors based on 3 and 4 exhibit maximum electron mobilities up to 0.22 and 0.16 cm2 V?1 s?1, respectively, with on‐off current ratios (Ion/Ioff) of more than than 106. Cyclic voltammetry analysis showed that this class of quinoidal derivatives exhibited excellent reversible two‐stage reduction behavior. This property was further investigated by a stepwise reductive titration of 4 , in which sequential reduction to the radical anion and then the dianion were observed. 相似文献
20.
Xue Min Ivan A. Popov Fu‐Xing Pan Dr. Lei‐Jiao Li Eduard Matito Prof. Dr. Zhong‐Ming Sun Prof. Dr. Lai‐Sheng Wang Prof. Dr. Alexander I. Boldyrev 《Angewandte Chemie (International ed. in English)》2016,55(18):5531-5535
Antiaromaticity, as introduced in 1965, usually refers to monocyclic systems with 4n π electrons. This concept was extended to all‐metal molecules after the observation of Li3Al4? in the gas phase. However, the solid‐phase counterparts have not been documented to date. Herein, we describe a series of all‐metal antiaromatic anions, [Ln(η4‐Sb4)3]3?(Ln=La, Y, Ho, Er, Lu), which were isolated as the K([2.2.2]crypt) salts and identified by single‐crystal X‐ray diffraction. Based on the results obtained from the chemical bonding analysis, multicenter indices, and the electron‐counting rule, we conclude that the core [Ln(η4‐Sb4)3]3? fragment of the crystal has three locally π‐antiaromatic Sb4 fragments. This complex represents the first locally π‐antiaromatic all‐metal system in the solid state, which is stabilized by interactions of the three π‐antiaromatic units with the central metal atom. 相似文献