Conductive Nanoscopic Fibrous Assemblies Containing Helical Tetrathiafulvalene Stacks

Tatewaki, Yoko; Hatanaka, Tatsuya; Tsunashima, Ryo; Nakamura, Takayoshi; Kimura, Mutsumi; Shirai, Hirofusa

doi:10.1002/asia.200900044

Cited by 54 publications

(37 citation statements)

References 66 publications

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“…In the case of 1D charge-transfer (CT) assemblies of oxidized TTFs and other electron acceptors, high electronic conductivity is strongly dependent upon the magnitude of intermolecular CT interactions and the length of the stacks. [70] In this context, a combination of intermolecular hydrogen bonding and charge-transfer complex formation has been used for making stable conductive TTF nanofibers of 29. In the presence of a stoichiometric amount of the electron acceptor 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4TCNQ), 29 yielded a dark-colored CT gel with electrical conductivity of 5.0 10 À4 S cm À1 .…”

Section: Angewandte Minireviewsmentioning

confidence: 99%

Self‐Assembled Gelators for Organic Electronics

2012

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Nature excels at engineering materials by using the principles of chemical synthesis and molecular self-assembly with the help of noncovalent forces. Learning from these phenomena, scientists have been able to create a variety of self-assembled artificial materials of different size, shapes, and properties for wide ranging applications. An area of great interest in this regard is solvent-assisted gel formation with functional organic molecules, thus leading to one-dimensional fibers. Such fibers have improved electronic properties and are potential soft materials for organic electronic devices, particularly in bulk heterojunction solar cells. Described herein is how molecular self-assembly, which was originally proposed as a simple laboratory curiosity, has helped the evolution of a variety of soft functional materials useful for advanced electronic devices such as organic field-effect transistors and organic solar cells. Highlights on some of the recent developments are discussed.

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Section: Angewandte Minireviewsmentioning

confidence: 99%

Self‐Assembled Gelators for Organic Electronics

2012

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“…17 The gel of the helical nanofibers composed of S-TTF and F 4 TCNQ showed a conductivity of 10 ¹4 S cm ¹1 . 18 From the above, the complex of TTF-4FcF 2 TCNQ provided the typical semiconducting conductivity.…”

Section: ¹1mentioning

confidence: 92%

Synthesis and Physical Properties of Tetrathiafulvalene Derivatives with Ferrocene-terminated Substituents

Tatewaki¹,

Mizuguchi²,

Kato³

et al. 2014

Chemistry Letters

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A TTF derivative with ferrocene-terminated substituents TTF-4Fc was found to form elliptic nanoaggregates by the interaction of the hydrogen-bond networks of amide groups. Electric conductivity of the film composed of TTF-4Fc F 2 TCNQ is determined to be 1.6 © 10 ¹4 S cm ¹1.Conducting nanostructures are one of the important building blocks to create feature nanoscale materials for electronics. 1Nanostructures are constructed utilizing intermolecular interactions such as charge transfer (CT), hydrogen bonding, and van der Waals interactions. Supramolecular approaches have structural flexibility, and they are effective methods to obtain novel low-dimensional nanostructured molecular assemblies. 24Among the π-conjugated molecules, tetrathiafulvalenes (TTFs) have been investigated as molecular metals in the supramolecular states. 58 The CT complexes composed of TTF and acceptor molecules show high electric conductivities. Their conductivity strongly depends on the magnitude of the intermolecular CT interactions between the donor and acceptor molecules. Ueno synthesized the first compound belonging to TTF derivatives with ferrocene as a substituent, which formed CT complexes with TCNQ or DDQ.9 A few reports have appeared dealing with the electrochemical properties and CT complexes of TTF having a ferrocene moiety. 1012 These findings have prompted us to synthesize and investigate the electrochemical properties of novel TTF derivative separated by the insertion of a ferrocene moiety as a conjugated spacer between the TTFs. In this paper, we report the synthesis of a symmetric TTF derivative having four N-[1-(4-ferrocenylphenyl)ethyl]amide termini TTF-4Fc in Scheme 1 and its CT complex with 2,5-difluoro-7,7,8,8-tetracyanoquinodimethane (F 2 TCNQ), i.e., TTF-4FcF 2 TCNQ, and describe the self-organization of TTF-4Fc into nanoaggregates. The temperature dependence of electrical conductivities of the cast film composed of TTF-4FcF 2 TCNQ was investigated.TTF-4Fc was synthesized according to Scheme 1. TTF-4Fc was isolated by silica gel column chromatography using ethyl acetatechloroform (1:9) as an eluent and characterized by 1 H and 13 C NMR spectroscopies. 13 The CT complex was prepared by mixing TTF-4Fc chloroform solution (1 mM) and F 2 TCNQ acetonitrile solution (1 mM) in 1:1 volume ratio. The cast films of the CT complex TTF-4FcF 2 TCNQ were formed by depositing this mixture solution on solid substrates. The atomic force microscope (AFM) images were taken by using a Seiko SPA 400 scanning probe microscope with an SPI 3800 probe station operating under the dynamic force mode. The redox potentials were obtained by using cyclic voltammetry (CV), and the experiments were carried out in a dry degassed dichloromethane solution of TTF-4Fc, and n-Bu 4 NBF 4 (0.1 mM) was added as a supporting electrolyte. The temperature-dependent electrical conductivity of the cast film was measured using a DC twoprobe method. Gold electrodes with an electrode gap of 500¯m were deposited by vacuum evaporation on a mica substrate, and then...

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“…Therefore, while maintaining the stacking of conductive molecular plane, the progression of one-dimensional growth will lead to the creation of new functional molecular devices. The fabrication of a nanometer-scale thin film having a fibril texture, which was achieved by incorporating a phenyl group in the TTF derivatives, has been reported previously [21]. However, the strong interactions between the molecules, which is a consequence of the competing forces of p-p interactions (of TTFs and phenyl rings) and hydrogen-bonding (of urethane bonding units), inhibited accurate morphological control.…”

Section: Introductionmentioning

confidence: 96%