Synthesis and Properties of (Propyleneditelluro)tetrathiafulvalene Donors

Tsutsui, Koji; Takimiya, Kazuo; Aso, Yoshio; Otsubo, Tetsuo

doi:10.1016/s0040-4039(97)01784-x

Cited by 9 publications

(6 citation statements)

References 7 publications

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“…As Figure 2(a) indicates, the crystal structure of 5 Á (TCNQ) comprises donor-acceptor (DA) type stacking columns and is different from that of the earlier reported TCNQF 2 complex of 4, which has DDAA type stacking columns [2]. There are several contacts less than the sum of the van der Waals radii [S Á Á Á Te (3.86 Å ) and Te Á Á Á Te (4.12 Å )], suggesting one-dimensional (1D) conductor along the side-by-side direction of the donor molecule Figure 2(b).…”

Section: Crystal Structures Of the Tcnq Complex And The Cation Radicamentioning

confidence: 60%

“…Furthermore conducting salts based on tellurium-containing donor molecules are interesting because the tellurium network in the crystal is dominant for the construction of whole the crystal structure [1]. Recently, several tellurocycle-fused donor molecules 174 have been reported [2]. Several studies have been made on their 7,7,8,8-tetracyanoquinodimethane (TCNQ) and 2,5-difluoro-TCNQ (TCNQF 2 ) complexes, however no cation radical salt has been reported.…”

Section: Introductionmentioning

confidence: 99%

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New organic conductors based on tellurium-containing donor molecules

Ojima

Fujiwara

Kobayashi

et al. 2002

Molecular Crystals and Liquid Crystals

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Trimethyleneditelluro-and trimethyleneoxaditelluro-substituted dimethyl-TTF derivatives were prepared. The CV result of the trimethyleneditellurosubstituted dimethyl-TTF derivative shows characteristic multi-redox behavior and the trimethyleneoxaditelluro-substituted dimethyl-TTF derivative exhibits two pairs of reversible redox waves. The structures and physical properties of conducting salts based on their donors are also clarified.

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Section: Crystal Structures Of the Tcnq Complex And The Cation Radicamentioning

confidence: 60%

Section: Introductionmentioning

confidence: 99%

New organic conductors based on tellurium-containing donor molecules

Ojima

Fujiwara

Kobayashi

et al. 2002

Molecular Crystals and Liquid Crystals

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“…Similar multi-redox voltammograms have been observed for the earlier reported tellurocycle-fused TTF donors (3±6). [6] When we repeated sweeping cycles between 0.0 V and 1.2 V, all three redox waves of 7 did not change at all. However, repeated cycling between 0.0 V and 1.5 V (higher than a shoulder peak around 1.4 V) gradually extinguished only the third redox wave, which completely disappeared after 20 cycles (see Fig.…”

Section: Synthesis Structures and Properties Of New Organic Conductmentioning

confidence: 89%

“…As shown in Figure 3b, the crystal structure of the complex comprises donor±acceptor (DA) type stacking columns and is different from that of the earlier reported TCNQF 2 complex of 6, which has DDAA type stacking columns. [6] There are several S±Te and Te±Te contacts less than the sum of the van der Waals radii [S±Te(3.86 ) and Te±Te(4.12 )], suggesting one-dimensional character along the side-by-side direction (the a-axis) (Fig. 3c).…”

Section: Synthesis Structures and Properties Of New Organic Conductmentioning

confidence: 99%

“…[5] Recently the propyleneditelluro-substituted TTF derivatives 3±6 have been reported as the first examples of tellurocycle-fused TTF donor molecules. [6] Several studies have been made on their 7,7,8,8-tetracyanoquinodimethane (TCNQ) and 2,5-difluoro-TCNQ (TCNQF 2 ) complexes; however, no cation radical salt has been reported. Therefore we focused on other tellurocycle-fused TTF donor molecules.…”

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confidence: 99%

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Synthesis, Structures, and Properties of New Organic Conductors Based on Tellurocycle-Fused TTF Donor Molecules

Ojima

Fujiwara

Kobayashi³

et al. 1999

Adv. Mater.

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The advance of organic conductors has been accelerated by the emergence of novel molecular systems. In the search for excellent electron donors for organic conductors, interest in tellurium-containing tetrathiafulvalene (TTF) derivatives has grown over the last few years because a new metallic system with wide bandwidth and high dimensionality is expected due to the large electron cloud of tellurium atoms. [1] In addition, conducting salts based on telluriumcontaining donor molecules are interesting because the tellurium network is a dominant factor in the arrangement of the whole crystal structure. [2] For example, the investigation of tellurium-substituted TTFs has been performed on tetrakis(alkyltelluro)-and (phenyltelluro)-TTFs (1 [3] and 2 [4] ) and yielded the discovery of tetrakis(methyltelluro)-TTF (1, n = 1) as a high-mobility single-component organic semiconductor owing to the two-dimensional tellurium network. [5] Recently the propyleneditelluro-substituted TTF derivatives 3±6 have been reported as the first examples of tellurocycle-fused TTF donor molecules. [6] Several studies have been made on their 7,7,8,8-tetracyanoquinodimethane (TCNQ) and 2,5-difluoro-TCNQ (TCNQF 2 ) complexes; however, no cation radical salt has been reported. Therefore we focused on other tellurocycle-fused TTF donor molecules. In this communication we report the synthesis, crystal structure, and electrochemical properties of a new tellurocycle-fused TTF donor, 4,5-dimethyl-4¢,5¢-propyleneditelluro-TTF (7), and crystal structures and electrical properties of the charge-transfer complex and cation radical salts prepared from 7.The tellurocycle-fused TTF donor 7 was synthesized as shown in Scheme 1. Lithiation of dimethyl-TTF (DMTTF) [7] with lithium diisopropylamide (LDA), followed by treatment with elemental tellurium generated dilithium 4,5-dimethyl-TTF-4¢,5¢-ditellurolate, which was then reacted with 1,3-dibromopropane. The donor 7 was obtained as air-stable red±brown crystals in 8 % yield. Scheme 1. Synthesis of 7. Reagents and conditions: i) LDA (2.2 equiv.), dry THF, ±78 C, 2.5 h; ii) Te (2.0 equiv.), ±78 to 0 C, 6 h; iii) Br(CH 2 ) 3 Br (1.0 equiv.), ±78 C to room temperature, overnight. X-ray crystallographic analysis was performed on a single crystal of 7 recrystallized from carbon disulfide/n-heptane. There are five crystallographically independent donor molecules, and five periodic sigmoidal stackings are formed along the c-axis. The TTF moieties have a bent structure resembling the molecular structure of neutral bis(ethylenedithio)-TTF (BEDT-TTF) [8] and the propyleneditelluro groups adopt a chair conformation (Fig. 1). Fig. 1. The crystal structure of neutral molecule 7 viewed along the molecular short axis.The electrochemical properties of 7 were investigated by cyclic voltammetry. The cyclic voltammogram was measured in PhCN containing tetra-n-butylammonium perchlorate at 20 C. The donor molecule 7 showed three pairs of reversible redox waves at +0.37, +0.76, and +0.88 V vs. Ag/ AgCl (inset of Fig. 2). On the...

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Novel Organotellurium Heterocycles Derived From Bis(2‐Aminophenyl) Ditelluride

Sanford

Walker

Fronczek

et al. 2016

Journal of Heterocyclic Chem

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Novel methods for the preparation of organotellurium heterocycles derived from bis(2‐aminophenyl) ditelluride were developed. Thus, highly nucleophilic 2‐aminobenzenetellurol generated by reduction in situ reacted smoothly with malonitrile to 2‐cyanomethylbenzo‐1,3‐tellurazole, while its treatment with carbon disulfide and subsequent methylation generated 2‐methylmercaptobenzo‐1,3‐tellurazole. Amidation to (2‐haloacetamidophenyl) ditellurides, followed by reduction under carefully controlled conditions, furnished previously inaccessible 2H‐1,4‐benzotellurazin‐3(4H)‐ones in yields ranging from 47‐62%.

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Synthesis and Properties of (Propyleneditelluro)tetrathiafulvalene Donors

Cited by 9 publications

References 7 publications

New organic conductors based on tellurium-containing donor molecules

New organic conductors based on tellurium-containing donor molecules

Synthesis, Structures, and Properties of New Organic Conductors Based on Tellurocycle-Fused TTF Donor Molecules

Novel Organotellurium Heterocycles Derived From Bis(2‐Aminophenyl) Ditelluride

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