Dibenzotetrathiafulvalene Bisimides: New Building Blocks for Organic Electronic Materials**

Gao, Xike; Wang, Ying; Yang, Xiaodi; Liu, Yunqi; Qiu, Weibin; Wu, Weiping; Zhang, Hengjun; Qi, Ting; Liu, Ying; Lü, Kun; Du, Chunfang; Shuai, Zhigang; Yu, Gui; Zhu, Daoben

doi:10.1002/adma.200700007

Cited by 54 publications

(49 citation statements)

References 30 publications

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“…The incorporation of the ester groups have the additional advantage of imparting good solubility to the compounds, permitting the preparation of OFET devices with single crystals of the TTF derivatives grown from solution, and giving an improved stability to de prepared devices. In all cases, the crystal structure of the compounds shows slip-stacks of dimers in contrast with the TTF derivatives that are symmetrically substituted such as DB-TTF 32 and dibenzotetrathiafulvalene bisimides, 9 in which regular columns of molecules are formed. The DFT quantum-chemical calculations carried out point to relatively high reorganization energy in all compounds.…”

Section: Resultsmentioning

confidence: 99%

“…General procedure for the synthesis of phthaloyldithiolones (11-14). A solution of the corresponding N-substituted maleimide (7)(8)(9)(10)4.10 mmol) and 3,4-bis(bromomethyl)dithiolone (8.20 mmol), in dry DMF (25 ml), was refluxed for 8 hours under argon. Then, the solvent was partially removed under vacuum and the residue mixed with water and extracted with n-hexane/diethylether 3015,2974,1766,1696,1601,1463,1436,1390,1335,1203,1189,1144,1099,1057,973,919,875,851,765,746; m/z (MALDI) 252 (100, M + -27, +H -CO); Elemental analysis calcd (%) for C 12 H 9 NO 3 S 2 : C, 51.60; H, 3.25; N, 5.01; S, 22.96; found C, 51.48; H, 3.19; N, 4.95; S, 22.80.…”

Section: Synthesis Of Bdc-ttf (6)mentioning

confidence: 99%

“…1 TTF and its derivatives have been thoroughly used as components of organic conductors, 2 but only recently, it has been shown that TTF derivatives are very promising materials for the preparation of OFETs owing to their processability and high device performance. [3][4][5][6][7][8][9] OFETs using TTFs as semiconductors have been prepared either from vacuum deposition or from solution. Soluble semiconductors are highly desired since they are compatible with low-cost deposition techniques (i.e.…”

Section: Introductionmentioning

confidence: 99%

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Benzodicarbomethoxytetrathiafulvalene Derivatives as Soluble Organic Semiconductors

et al. 2010

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RECEIVED DATE (to be automatically inserted after your manuscript is accepted if required according to the journal that you are submitting your paper to)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 2 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 x 10 -3 cm 2 /V 1 s 1 .

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Section: Resultsmentioning

confidence: 99%

Section: Synthesis Of Bdc-ttf (6)mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Benzodicarbomethoxytetrathiafulvalene Derivatives as Soluble Organic Semiconductors

et al. 2010

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“…28 The resulting planar π-expanded molecules had lower-lying HOMO levels (-5.4 eV) relative to that of DB-TTF (37) (-4.97 eV). OFET devices based on (47) and (48) …”

Section: Thieno[32-b]thiophene Derivativesmentioning

confidence: 95%

π-Conjugated molecules with fused rings for organic field-effect transistors: design, synthesis and applications

2010

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. π-Conjugated molecules with fused rings for organic field-effect transistors: design, synthesis and applications. Chemical Society Reviews, 39(5), pp. 1489-1502. doi: 10.1039/b813123f This is the accepted version of the paper.This version of the publication may differ from the final published version. π-Conjugated molecular materials with fused rings are the focus of considerable interest in the emerging area of organic electronics, since the combination of excellent charge carrier mobility and high stability may lead to their practical applications. This tutorial review discusses the synthesis, properties and applications of π-conjugated organic semiconducting materials especially those with fused rings. The achievements to date, the remaining problems and challenges, and the key research that needs to be done in the near future are all discussed. Permanent Snappy text:The synthesis, properties and applications of π-conjugated organic semiconductors especially those with fused rings are discussed in this tutorial review.

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“…Compound 40 has electron donor-acceptor parts leading to a π-stacking structure by an intermolecular charge-transfer interaction in the crystal, whereas TTFs 37 and 39 assume herringbone structures. Following a similar idea, electron-accepting diimide groups were introduced to dibenzoTTF to yield high hole mobility of 0.40 cm 2 Vs −1 in 41 [42]. Pyrrole-fused derivatives 42 have an advantage of good solubility, facilitating solution processing [43].…”

Section: Tetrathiafulvalenesmentioning

confidence: 99%

Organic semiconductors for organic field-effect transistors

Yamashita¹

2009

Science and Technology of Advanced Materials

265

146

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The advantages of organic field-effect transistors (OFETs), such as low cost, flexibility and large-area fabrication, have recently attracted much attention due to their electronic applications. Practical transistors require high mobility, large on/off ratio, low threshold voltage and high stability. Development of new organic semiconductors is key to achieving these parameters. Recently, organic semiconductors have been synthesized showing comparable mobilities to amorphous-silicon-based FETs. These materials make OFETs more attractive and their applications have been attempted. New organic semiconductors resulting in high-performance FET devices are described here and the relationship between transistor characteristics and chemical structure is discussed.

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Dibenzotetrathiafulvalene Bisimides: New Building Blocks for Organic Electronic Materials**

Abstract: COMMUNICATION 3038www.advmat.de

Cited by 54 publications

References 30 publications

Benzodicarbomethoxytetrathiafulvalene Derivatives as Soluble Organic Semiconductors

Benzodicarbomethoxytetrathiafulvalene Derivatives as Soluble Organic Semiconductors

π-Conjugated molecules with fused rings for organic field-effect transistors: design, synthesis and applications

Organic semiconductors for organic field-effect transistors

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