- A hydrogen-bonded organic framework based on redox-active tri(dithiolylidene)cyclohexanetrione
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Redox-active hexakis(4-carboxyphenyl) tri(dithiolylidene)cyclohexanetrione (CPDC) was synthesized. The CPDC-based porous framework, constructedviaanomalistic helical hydrogen-bonding, exhibites permanent porosity and photoconductivity.
- Shivakumar, Kilingaru I.,Noro, Shin-Ichiro,Yamaguchi, Yuna,Ishigaki, Yusuke,Saeki, Akinori,Takahashi, Kiyonori,Nakamura, Takayoshi,Hisaki, Ichiro
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- Synthesis of 4-aryl-and 4-acyl-1,3-dithiole-2-thiones via deprotonative zincation of 1,3-dithiole-2-thione
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We have developed deprotonative zincation of 1,3-dithiole- 2- thione at the 4-position. Addition of lithium diisopropylamide to a THF solution of 1,3-dithiole- 2- thione containing ZnI2 and LiI generated the corresponding organozinc species. After this zincation, various aryl and acyl groups were installed at the 4-position by Pd-catalyzed cross-coupling reaction with aryl iodides and Cu-catalyzed acylation with acyl chlorides, respectively.
- Otsuka, Shinya,Yorimitsu, Hideki
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- Selective Metalation of 1,3-Dithiole-2-thiones: An Effective Preparation of New Symmetrically and Nonsymmetrically Tetraarylated Tetrathiafulvalenes
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We report an efficient preparation of fully functionalized tetrathiafulvalene derivatives (TTF) with an extended π-system via a selective magnesiation of 1,3-dithiole-2-thiones (DTT) using 2,2,6,6-tetramethylpiperidin-1-ylmagnesium chloride-lithium chloride (TMPMgCl·LiCl); subsequent reaction with various electrophiles, such as halides, acid chlorides, allyl bromides, and aryl iodides, smoothly led to new mono- and difunctionalized 1,3-dithiole-2-thione derivatives. A triethyl phosphite mediated cross-coupling of the disubstituted 1,3-dithiole-2-thione derivatives with their oxygen analogues gave access to new symmetrically and nonsymmetrically tetraarylated tetrathiafulvalenes of interest as organic materials.
- Nafe, Julia,Knochel, Paul
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p. 103 - 114
(2015/12/26)
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- The 1,2,3-thiadiazole route to new vinylogue tetrathiafulvalenes
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Cleavage of 1,4-dithiafulvene-substituted 1,2,3-thiadiazoles with base and dimerisation of the resulting alkyne-1-thiolate gives new tetrathiafulvalene-type vinylogue extended π-donors in a one pot reaction. The solvent-/base-system used (acetonitrile/NaH) was optimised for the synthesis of 1,3-dithiole-2-thiones via this route. Efficient synthesis of the important 4-formyl-1,3-dithiol-2-thione and its coupling to 2,6(7)-bisformyltetrathiafulvalene is presented. Preparation of a number of new 1,4-dithiafulvenes are reported.
- Clausen, Rasmus P.,Becher, Jan
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p. 3171 - 3188
(2007/10/03)
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