共查询到20条相似文献,搜索用时 15 毫秒
1.
Naraso N Nishida J Ando S Yamaguchi J Itaka K Koinuma H Tada H Tokito S Yamashita Y 《Journal of the American Chemical Society》2005,127(29):10142-10143
Aromatic ring-condensed TTF derivatives exhibited excellent p-type FET performances in thin films. Introduction of fused benzene and pyrazine rings to the TTF skeleton was effective to enhance the intermolecular interactions and stability to oxygen. Ordered molecular alignment was confirmed by XRD studies. A pi-stacking structure was observed in the single crystal of diquinoxalinoTTF. 相似文献
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Nielsen MB Jeppesen JO Lau J Lomholt C Damgaard D Jacobsen JP Becher J Stoddart JF 《The Journal of organic chemistry》2001,66(10):3559-3563
The complexation between a number of different pi-electron donating TTF derivatives and the pi-electron accepting tetracationic cyclophane cyclobis(paraquat-p-phenylene) (CBPQT(4+)) has been studied by (1)H NMR and UV-vis spectroscopy. The results demonstrate that the strength of association between the donors (TTF derivatives) and acceptor (CBPQT(4+)) is strongly dependent on the pi-electron donating properties (measured by the first redox potential ) of the TTF derivatives. However, the first redox potential () is not the only factor of importance. The extended pi-surface of the TTF derivatives also exerts a stabilizing influence upon complexation. The kinetics for the complexation-decomplexation were studied using (1)H NMR spectroscopy and are related to the bulkiness of the TTF derivatives. These effects may serve to improve the design of interlocked molecular systems, especially (bistable) molecular switches, in which CBPQT(4+) and a derivatized TTF unit are incorporated. 相似文献
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两个多核四硫代富瓦烯类衍生物的合成和电化学行为 总被引:2,自引:0,他引:2
合成了2个含3个四硫代富瓦烯单元的化合物,给出了它们的核磁共振氢谱、质谱、紫外吸收光谱及元素分析数据。用循环伏安法测定了它们的氧化还原电位,并将其与仅含1个或2个四硫代富瓦烯单元的化合物的氧化还原电位比较。发现随着分子内共轭程度的增加,分子内的库仑斥力也随之降低。 相似文献
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Ryota Ueno Daishi Fujino Prof. Dr. Hideki Yorimitsu Prof. Dr. Atsuhiro Osuka 《Chemistry (Weinheim an der Bergstrasse, Germany)》2013,19(22):7156-7161
Triisopropylsilyltetrathiafulvalene (TIPS‐TTF) has been devised as a promising platform for the synthesis of low‐symmetry TTF derivatives. The bulky TIPS group allows TIPS‐TTF to undergo palladium‐catalyzed direct diarylation as well as LDA‐mediated dilithiation exclusively on the roomier dithiole ring. Subsequent fluoride‐mediated protodesilylation provided vicinally difunctionalized TTF, which could undergo further functionalization. 相似文献
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Nakamura K Takashima T Shirahata T Hino S Hasegawa M Mazaki Y Misaki Y 《Organic letters》2011,13(12):3122-3125
New dimeric and trimeric TTF derivatives with methylenedithio spacers (1a,b, 2a, and 2b) have been synthesized. X-ray structure analysis revealed that TTF units of the dimer 1b adopted distorted face-to-face overlapping arrangement both in intra- and intermolecular stacking. Cyclic voltammetric study indicated that trimeric 2a was in favor of taking di- and tetracationic states, while the dimeric 1a was in favor of taking a monocation. The absorption spectroscopic study suggested an existence of the strong face-to-face interaction particularly in di-, tri-, and tetracationic state of the trimeric TTF derivatives. 相似文献
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Michel Guerro 《Tetrahedron》2009,65(31):6123-8746
A series of tetrathiafulvalene (TTF) derivatives functionalized by one or two β-diketonatoboron difluoride groups were synthesized through the addition of borontrifluoride to TTF substituted by one or two acetylacetone functions. The influence of the β-diketonatoboron difluoride moiety on the redox properties of the TTF has been investigated by cyclic voltammetry. 相似文献
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Tetrathiafulvalene (TTF) and its derivatives were originally prepared as strong electron-donor molecules for the development of electrically conducting materials. This Review emphasizes how TTF and its derivatives offer new and in some cases little-exploited possibilities at the molecular to the supramolecular levels, as well as in macromolecular aspects. TTF is a well-established molecule whose interest goes beyond the field of materials chemistry to be considered an important building block in supramolecular chemistry, crystal engineering, and in systems able to operate as machines. At the molecular level, TTF is a readily available molecule which displays a strong electron-donor ability. However, its use as a catalyst for radical-polar crossover reactions, thus mimicking samarium iodide chemistry, has only recently been addressed. Important goals have been achieved in the use of TTF at the macromolecular level where TTF-containing oligomers, polymers, and dendrimers have allowed the preparation of new materials that integrate the unique properties of TTF with the processability and stability that macromolecules display. The TTF molecule has also been successfully used in the construction of redox-active supramolecular systems. Thus, chemical sensors and redox-switchable ligands have been prepared from TTF while molecular shuttles and molecular switches have been prepared from TTF-containing rotaxanes and catenanes. A large synthetic effort has been devoted to the preparation of the so-called organic ferromagnets, many of which are derived from TTF. The main task in these systems is the introduction of ferromagnetic coupling between the conduction electrons and localized electrons. TTF has also played a prominent role in molecular electronics where TTF-containing D-sigma-A molecules have allowed the preparation of the first confirmed unimolecular rectifier. Recently, it has been confirmed that TTF can display efficient nonlinear optic (NLO) responses in the second and third harmonic generation as well as a good thermal stability. These findings can be combined with the redox ability of TTF as an external stimuli to provide a promising strategy for the molecular engineering of switchable NLO materials. Fullerenes endowed with TTF exhibit outstanding photophysical properties leading to charge-separated (CS) states that show remarkable lifetimes. 相似文献
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Terkia-Derdra N Andreu R Salle M Levillain E Orduna J Garin J Orti E Viruela R Pou-Amerigo R Sahraoui B Gorgues A Favard JF Riou A 《Chemistry (Weinheim an der Bergstrasse, Germany)》2000,6(7):1199-1213
A series of extended tetrathiafulvalene (TTF) derivatives bearing one or two 1,4-dithiafulven-6-yl substitutents has been prepared. The new compounds present remarkable electrochemical singularities compared with other TTF derivatives, which are strongly affected by the nature of the substitution on the lateral heterocycle(s). This unusual electrochemical behaviour follows a square-scheme sequence and is attributed to structural changes upon oxidation of the pi-donating molecules. Digital simulations of the electrochemical data have been used to reach the values of the kinetic and thermodynamic constants involved in the square scheme. Theoretical calculations establish an important contribution of a highly delocalised resonant form involving a tetravalent sulphur in oxidised species, which could justify the occurrence of an electrochemical behaviour distinct from that of TTF. Finally, third-order susceptibilities chi 3 of two of these systems, for which electron-donating and electron-withdrawing substituents coexist and are conjugated through the TTF pi system, are given. 相似文献
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Kojima T Nishida J Tokito S Tada H Yamashita Y 《Chemical communications (Cambridge, England)》2007,(14):1430-1432
New oligomers containing a pyrazine unit have been prepared: the bithienyl derivatives afforded p-type FET devices whereas the trifluoromethylphenyl derivatives showed n-type FET behavior. 相似文献
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新型四硫富瓦烯硫杂冠醚衍生物的合成 总被引:4,自引:0,他引:4
在高度稀释条件下, 经4,5-二溴甲基-1,3-二硫杂环戊烯-2-硫酮(7)和多缩乙二醇的1,ω-二巯基衍生物的缩合反应, 方便地合成了4,5-位带二硫杂冠醚残基的2-硫代-1,3-二硫杂环戊烯的衍生物8a~8d, 中间体硫杂冠醚8c~8d的合成中有明显的“模板效应”. 在亚磷酸三乙酯存在下, 8a~8d经自偶联生成新型的对称双臂四硫富瓦烯(TTF)硫杂冠醚衍生物10a~10d, 而与4,5-二甲硫基-1,3-二硫杂环戊烯-2-酮(9)经交叉偶联生成新型的非对称单臂四硫富瓦烯硫杂冠醚衍生物11a~11d. 用循环伏安法研究了上述目标化合物的电化学性质和离子传感性质. 相似文献
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We calculated the hole and electron mobilities of tetrathiafulvalene (TTF) derivative crystals using first-principles calculations and the Marcus theory of electron transfer. The hole and electron reorganization energies were found to decrease with the extension of π-conjugated orbitals. The calculated hole mobilities of TTF, dibenzo-tetrathiafulvalene (DB-TTF), and dinaphtho-tetrathiafulvalene (DN-TTF) agree well with the experimental results. In addition, with the increase of the number of benzene rings attached to the TTF skeleton, the hole mobilities decrease and the electron mobilities increase. The calculated electron mobility of dianthro-tetrathiafulvalene (DA-TTF) based on a virtual crystal structure is much larger than the hole one due to the small electron reorganization energy and large electron coupling. This suggests that the charge transfer properties of the TTF derivatives can be modified when the number of aromatic rings on TTF skeleton increases. 相似文献
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Otón F Pfattner R Oxtoby NS Mas-Torrent M Wurst K Fontrodona X Olivier Y Cornil J Veciana J Rovira C 《The Journal of organic chemistry》2011,76(1):154-163
A series of new tetrathiafulvalene (TTF) derivatives bearing dimethoxycarbonyl and phenyl or phthalimidyl groups fused to the TTF core (6 and 15-18) has been synthesized as potential soluble semiconductor materials for organic field-effect transistors (OFETs). The electron-withdrawing substituents lower the energy of the HOMO and LUMO levels and increase the solubility and stability of the semiconducting material. Crystal structures of all new TTF derivatives are also described, and theoretical DFT calculations were carried out to study the potential of the crystals to be used in OFET. In the experimental study, the best performing device exhibited a hole mobility up to 7.5 × 10(-3) cm(2) V(-1) s(-1)). 相似文献
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M. Ángeles Herranz Luis Sánchez Nazario Martín 《Phosphorus, sulfur, and silicon and the related elements》2013,188(5-6):1133-1148
Abstract Tetrathiafulvalene (TTF) and its derivatives are exceptional building blocks in many areas of organic, supramolecular, and materials chemistry. Since the discovery ca. 30 years ago of the first “organic metal” tetrathiafulvalene-tetracyano-p-quinodimethane (TTF-TCNQ), a huge number of TTF derivatives have been synthetized. Although initial efforts were directed to enhance the electron-donating ability of TTF analogues to improve the conductivities of salts and charge-transfer (CT) complexes derived from them, the developments in synthetic TTF chemistry have made it possible to incorporate TTF into more sophisticated structures such as materials exhibiting intramolecular charge-transfer and nonlinear optical properties, sensors, molecular shuttles and devices. Compounds in which TTF and electron-accepting molecules, especially C 60 , are covalently tethered exhibit outstanding photophysical properties leading, upon photoexcitation, to charge-separated (CS) states showing remarkable lifetimes. In these systems, the gain of aromaticity upon oxidation of the TTF moiety has been used as a new concept for improving the stability of the charge-separated state, and, therefore, are of interest for the preparation of artificial photosynthetic systems as well as photovoltaic devices. 相似文献
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四硫富瓦烯及其衍生物是性能优良的电子给体.本文利用Sonogashira反应将吡啶基团连接在四硫富瓦烯单元上,合成了"A-C≡C-TTF-C≡C-A"型四硫富瓦烯共轭体系衍生物4,4′(5′)-二-(4-吡啶乙炔基)-四硫富瓦烯(TTF4N).吸收光谱、电化学和Pb2+配位键合研究表明,三键作为桥基能够有效实现分子内的电荷转移.金属Pb2+离子与吡啶基团的配位能够引起TTF4N的吸收光谱、核磁氢谱和电化学性质的显著变化. 相似文献
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综述了一类有机-无机超分子组装体系四硫富瓦烯─多酸分子杂化材料近年来的研究进展。分述了Keggin型杂多阴离子、Dawson-Wels型杂多阴离子、Lindguist型同多阴离子以及含有顺磁性过渡金属原子的多阴离子的四硫富瓦烯和双乙基四硫富瓦烯的荷移盐和游离基离子盐的结构特征与导电性质,有机与无机亚单元间的磁交换性质介绍了杂多阴离子的低聚四硫富瓦烯盐的新进展 相似文献