Novel Electron Acceptors Bearing a Heteroquinonoid System. 4. Syntheses, Properties, and Charge-Transfer Complexes of 2,7-Bis(dicyanomethylene)-2,7-dihydrobenzo[2,1-b:3,4-b']dithiophene, 2,7-Bis(dicyanomethylene)-2,7-dihydrobenzo[1,2-b:4,3-b']dithiophene, and 2,6-Bis(dicyanomethylene)-2,6-dihydrobenzo[1,2-b:4,5-b']dithiophene

Yoshida, Shu; Fujii, Michihiko; Aso, Yoshio; Otsubo, Tetsuo; Ogura, Fumio

doi:10.1021/jo00090a027

Cited by 58 publications

(26 citation statements)

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“…Selective syntheses of the angular-shaped isomers ( 22 and 23 ) were achieved from 2-or 3-thiophene aldehyde, respectively (Scheme 6 c,d). [ 67 ] The synthesis of linear ADTs ( 3 ) was achieved via reduction of the corresponding ADT-5,11-diones [ 13 , 68 ] that were prepared from thiophene-2,3-dicarbaldehyde and 1,4-cyclohexadione under basic conditions ( Scheme 7 a). [ 69 ] Although this synthesis was straightforward, it inevitably afforded an inseparable mixture of anti-and syn-isomeric ADTs.…”

Section: Discussionmentioning

confidence: 99%

Thienoacene‐Based Organic Semiconductors

et al. 2011

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Thienoacenes consist of fused thiophene rings in a ladder-type molecular structure and have been intensively studied as potential organic semiconductors for organic field-effect transistors (OFETs) in the last decade. They are reviewed here. Despite their simple and similar molecular structures, the hitherto reported properties of thienoacene-based OFETs are rather diverse. This Review focuses on four classes of thienoacenes, which are classified in terms of their chemical structures, and elucidates the molecular electronic structure of each class. The packing structures of thienoacenes and the thus-estimated solid-state electronic structures are correlated to their carrier transport properties in OFET devices. With this perspective of the molecular structures of thienoacenes and their carrier transport properties in OFET devices, the structure-property relationships in thienoacene-based organic semiconductors are discussed. The discussion provides insight into new molecular design strategies for the development of superior organic semiconductors.

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Section: Discussionmentioning

confidence: 99%

Thienoacene‐Based Organic Semiconductors

et al. 2011

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“…The new 2D π‐conjugated 1 is formed by coupling of two thienoquinoidal cores in antiparallel fashion: a tetracyano quinoidal thiophene [23] ( MQ ) and a tetracyano quinoidal bithiophene [24] ( BQ ) in Figure 1 , the three thiophenes surrounding a benzenoid ring (i.e., generating a trapezoidal‐like form). [ 25 , 26 ] Tetracyanoquinoidal or tetracyanoquinodimethane (TCNQ)‐based π‐extended molecules are important electroactive units in the field of organic conductors[ 18 , 19 , 20 , 21 , 22 , 23 , 24 ] and organic electronics.…”

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confidence: 99%

A Trapezoidal Octacyanoquinoid Acceptor Forms Solution and Surface Products by Antiparallel Shape Fitting with Conformational Dipole Momentum Switch

et al. 2021

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A new compound (1) formed by two antiparallelly disposed tetracyano thienoquinoidal units has been synthesized and studied by electrochemistry, UV/Vis-NIR, IR, EPR, and transient spectroscopy. Self-assembly of 1 on a Au( 111) surface has been investigated by scanning tunneling microscopy. Experiments have been rationalized by quantum chemical calculations. 1 exhibits a unique charge distribution in its anionic form, with a gradient of charge yielding a neat molecular in-plane electric dipole momentum, which transforms out-of-plane after surface deposition due to twisted! folded conformational change and to partial charge transfer from Au(111). Intermolecular van der Waals interactions and antiparallel trapezoidal shape fitting lead to the formation of an optimal dense on Au(111) two-dimensional assembly of 1.

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“…Besides alkene 8, we also isolated, in 7% yield, the cis,cisdiene 14 (Figure 3), which was formed from the double Suzuki coupling on the 2,2¢-diiodobenzodithiophene (15) 9 ( Figure 3), an impurity persistently present as a by-product formed in the synthesis of compound 13, from which it is difficult to separate. The synthesis of alkenes 8 and 11 through the McMurry coupling required the preparation of the appropriate ketones 16 and 17 (Scheme 3).…”

Section: Synthesis Of 12-bis(benzodithienyl)ethenes 8 and 11mentioning

confidence: 99%

“…Bis(pinacolato)diboron was purchased from Sigma-Aldrich. Weinreb amide 19, 10 2-iodobenzodithiophene (13), 5 and 2,2¢diiodobenzodithiophene (15) 9 were prepared as reported.…”

Section: Functionalization Of Helicenementioning

confidence: 99%

Synthesis and Functionalization of Novel Tetrathia[7]helicenes as New Push-Pull Systems

Licandro¹,

Rigamonti²,

Ticozzelli³

et al. 2006

Synthesis

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The synthesis of new functionalized 1,2-bis(benzodithienyl)ethenes as well as the preparation of the new tetrathia[7]helicenes are described. The helicenes reported are new chiral pushpull molecules, with potential application in optoelectronics.[n]Heterohelicenes are very interesting all conjugated aromatic systems in which heteroaromatic units alternates with arene rings in an extended p-system. 1 When the number of ortho condensed rings [n] exceeds three, these systems are no more planar and they become chiral. The interconversion barrier between the two enantiomers depends on the number of aromatic rings and, for [n] greater than four, they are stereochemically stable compounds which means that their enantiomers can be separated and stored. 2The presence of heterocyclic rings can give some advantages with respect to carbohelicenes. In principle, it is possible to functionalize the heteroaromatic system regioselectively, thus opening the way for obtaining modified helicenes targeted for specific uses, and the tuning and monitoring of their properties. In particular, quite recently, tetrathia[7]helicenes ([7]THs) have attracted a great attention as potential new molecules with interesting optoelectronic properties. 3 In fact, both theoretical calculations 3b,c and experimental work 3a indicate them as new promising candidates for applications in non-linear optics. In particular, the computational study suggests that the presence of some appropriate electron-withdrawing and electron-donating substituents in the positions 2, 7, 8 and 13 of the helical system should improve their optoelectronic responses. 3c In addition to the above-mentioned potentialities, suitable functionalized [7]THs could be very interesting also as new chiral ligands to be use in catalysis. 4 For all these reasons, the search of new methods for the preparation of [7]THs and their functionalization is a highly desirable goal. Recently, 5 we have set up a new efficient synthesis of substituted [7]THs based on a Suzuki coupling of diboronic esters derivatives. More recently 6 we have studied new silyl substituted [7]THs, useful for the access to variously functionalized derivatives.In this paper we describe the preparation of [7]THs decorated with both electron-donating and electron-withdrawing substituents, in view of studying their non-linear optical properties. In particular, we focused our attention on the introduction of electron-donating and electronScheme 1 Strategies for the synthesis of substituted tetrathia[7]helicenes.

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Cited by 58 publications

References 1 publication

Thienoacene‐Based Organic Semiconductors

Thienoacene‐Based Organic Semiconductors

A Trapezoidal Octacyanoquinoid Acceptor Forms Solution and Surface Products by Antiparallel Shape Fitting with Conformational Dipole Momentum Switch

Synthesis and Functionalization of Novel Tetrathia[7]helicenes as New Push-Pull Systems

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