A new method for the synthesis of dinaphtho[1,2‐<i>b</i>;2′,1′‐<i>d</i>]thiophenes and selenophenes

Alam, Ashraful; Ohta, Hidetoshi; Yamamoto, Tatsuya; Ogawa, Satoshi; Sato, Ryo

doi:10.1002/hc.20291

Cited by 14 publications

(5 citation statements)

References 32 publications

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“…While the synthetic methodology of DN E –W s has already been developed, − applications of these materials to organic semiconductor devices have not been reported. First, we synthesized DN E –W s following the procedures described in the literature. , The ionization potentials of the vacuum-deposited thin films were determined by photoelectron yield spectroscopy to be 5.85 eV for DNF–W , 5.87 eV for DNT–W , and 5.81 eV for DNS–W , indicating that these materials could function as p-type materials.…”

Section: Resultsmentioning

confidence: 99%

“…First, we synthesized DNE−Ws following the procedures described in the literature. 15,18 The ionization potentials of the vacuumdeposited thin films were determined by photoelectron yield spectroscopy 19 to be 5.85 eV for DNF−W, 5.87 eV for DNT− W, and 5.81 eV for DNS−W, indicating that these materials could function as p-type materials.…”

Section: Resultsmentioning

confidence: 99%

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Dinaphtho[1,2-b:2′,1′-d]chalcogenophenes: Comprehensive Investigation of the Effect of the Chalcogen Atoms in the Phenacene-Type π-Electronic Cores

et al. 2013

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We report dinaphtho[1,2-b:2′,1′-d]chalcogenophenes as a new class of highly potential p-type semiconductors. As the result of comprehensive investigations including computational studies based on single-crystal structures successfully determined by X-ray analysis, the impacts of the chalcogen atoms are substantially manifested in their molecular orbitals, crystal packing structures, chargetransporting properties, and the device performances at the end. Among them, dinaphtho[1,2-b:2′,1′-d]thiophene and dinaphtho[1,2-b:2′,1′-d]selenophene achieved a hole mobility of up to 1.6 and 2.0 cm 2 V −1 s −1 , respectively, accompanied by an I on /I off ratio as high as 10 4 −10 5 in their single-crystal organic field-effect transistors. Such high performances are attributed to the large orbital coefficient on the chalcogen atoms and the ideal packing structures induced by chalcogen-bridged W-shaped molecules.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Dinaphtho[1,2-b:2′,1′-d]chalcogenophenes: Comprehensive Investigation of the Effect of the Chalcogen Atoms in the Phenacene-Type π-Electronic Cores

et al. 2013

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“…fonyl chlorides are available, including the Reed reaction (Reed, 1933(Reed, , 1934(Reed, , 1938, chlorosulfonation with chlorosulfonic acid (Alam et al, 2007), chlorination of sulfonic acid (Greig et al, 2006), etc. Chlorosulfonic acid is an easy to use eco-friendly reagent efficiently converting reactants to the corresponding sulfonyl chlorides.…”

Section: Preparation Of P-dodecyloxybenzenesulfonyl Chloride (Ix)mentioning

confidence: 99%

A new procedure for the synthesis of 2-[(4-dodecyloxyphenyl)sulfonyl]butanoic acid

Shi

Qian

Tao³

et al. 2015

Chemical Papers

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A new, practical and cost-effective route for scalable synthesis of 2-[(4-dodecyloxyphenyl)sulfonyl] butanoic acid, a key intermediate of a new cyan dye-forming coupler containing a sulfone group, was developed by adopting phenol as the starting material. The synthesis was accomplished in five steps with etherification, chlorosulfonation, reduction, nucleophilic reaction by C-S coupling and hydrolyzation. An important objective of the new synthetic route was the synthesis of 2-[4-(dodecyloxyphenyl)sulfonyl]butanoate. Overall yield obtained at optimized conditions increased to 66 %. The synthetic strategy was proven to be a process enabling rapid delivery of the target product with high purity.

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“…DNT‐1221 derivatives have been made from the reaction of naphthalene‐1‐sulfonic acid dimethylamide with n ‐butyllithium and S 8 in 29–37% yield . In addition, both DNT‐2112 and DNT‐1221 have been synthesized from dinaphthyl sulfides using a potassium tert ‐butoxide or n ‐butyllithium induced cyclodehydrogenation in 18–31% yield .…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Unsymmetric Monosubstituted and Disubstituted Dinaphthothiophenes

Throgmorton

Chintala

McCulla

2017

Journal of Heterocyclic Chem

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Dinaphthothiophenes (DNTs) are a class of compounds with potential uses in organic semiconductors and the synthesis of unsymmetric catalysts. Symmetrical or asymmetrical addition of functional groups to the DNT structure may be desired for steric bulk in binaphthyl catalyst synthesis or tuning the electronic properties of semiconductors. Thus, versatility of functional group addition is a great asset in DNT synthesis. Until now, no versatile and concise methods for the synthesis of unsymmetrically substituted DNTs have been reported. Herein, we report three synthetic routes for the creation of three different classes of DNTs. Each route involves the successive addition of two functionalized styryl groups to a thiophene ring, followed by a photocyclization to form the desired asymmetric DNT. Various novel unsymmetrically monosubstituted and disubstituted dinaphtho[2,1‐b:1′,2′‐d]thiophenes, dinaphtho[1,2‐b:1′,2′‐d]thiophenes, and dinaphtho[1,2‐b:2′,1′‐d]thiophenes were synthesized from 2‐bromothiophene,2,4‐dibromothiophene, and 3,4‐dibromothiophene in three or four steps. These methods can be used to synthesize a wide variety of unsymmetrically functionalized DNTs.

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A new method for the synthesis of dinaphtho[1,2‐b;2′,1′‐d]thiophenes and selenophenes

Cited by 14 publications

References 32 publications

Dinaphtho[1,2-b:2′,1′-d]chalcogenophenes: Comprehensive Investigation of the Effect of the Chalcogen Atoms in the Phenacene-Type π-Electronic Cores

Dinaphtho[1,2-b:2′,1′-d]chalcogenophenes: Comprehensive Investigation of the Effect of the Chalcogen Atoms in the Phenacene-Type π-Electronic Cores

A new procedure for the synthesis of 2-[(4-dodecyloxyphenyl)sulfonyl]butanoic acid

Synthesis of Unsymmetric Monosubstituted and Disubstituted Dinaphthothiophenes

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