135926-91-9Relevant academic research and scientific papers
Oligothiophene-Bridged Conjugated Covalent Organic Frameworks
Keller, Niklas,Bessinger, Derya,Reuter, Stephan,Calik, Mona,Ascherl, Laura,Hanusch, Fabian C.,Auras, Florian,Bein, Thomas
, p. 8194 - 8199 (2017)
Two-dimensional covalent organic frameworks (2D-COFs) are crystalline, porous materials comprising aligned columns of π-stacked building blocks. With a view toward the application of these materials in organic electronics and optoelectronics, the construction of oligothiophene-based COFs would be highly desirable. The realization of such materials, however, has remained a challenge, in particular with respect to laterally conjugated imine-linked COFs. We have developed a new building block design employing an asymmetric modification on an otherwise symmetric backbone that allows us to construct a series of highly crystalline quaterthiophene-derived COFs with tunable electronic properties. Studying the optical response of these materials, we have observed for the first time the formation of a charge transfer state between the COF subunits across the imine bond. We believe that our new building block design provides a general strategy for the construction of well-ordered COFs from various extended building blocks, thus greatly expanding the range of applicable molecules.
Hypervalent iodine(III): selective and efficient single-electron-transfer (SET) oxidizing agent
Dohi, Toshifumi,Ito, Motoki,Yamaoka, Nobutaka,Morimoto, Koji,Fujioka, Hiromichi,Kita, Yasuyuki
experimental part, p. 10797 - 10815 (2010/03/01)
In 1994, we first determined the single-electron-transfer (SET) oxidation ability of phenyliodine(III) bis(trifluoroacetate) (PIFA) toward phenyl ethers, affording the corresponding aromatic cation radicals. Since then, hypervalent iodine(III) has been utilized as a selective and efficient SET oxidizing agent that enables a variety of direct C-H functionalizations of aromatic rings in electron-rich arenes under mild conditions. We have now extended the original method to work in a series of heteroaromatic compounds such as thiophenes, pyrroles, and indoles. The investigations and results obtained since the start of this century are summarized in this article.
The synthesis of head-to-tail (H-T) dimers of 3-substituted thiophenes by the hypervalent iodine(III)-induced oxidative biaryl coupling reaction
Dohi, Toshifumi,Morimoto, Koji,Kiyono, Yorito,Maruyama, Akinobu,Tohma, Hirofumi,Kita, Yasuyuki
, p. 2930 - 2932 (2007/10/03)
The head-to-tail (H-T) dimers could be obtained selectively by the oxidative coupling reaction of 3-substituted thiophenes using a combination of hypervalent iodine(III) reagents and trimethylsilyl trifluoromethanesulfonate. The Roval Society of Chemistry 2005.
A novel and direct synthesis of alkylated 2,2′-bithiophene derivatives using a combination of hypervalent iodine(III) reagent and BF3·Et2O
Tohma, Hirofumi,Iwata, Minako,Maegawa, Tomohiro,Kiyono, Yorito,Maruyama, Akinobu,Kita, Yasuyuki
, p. 1647 - 1649 (2007/10/03)
A novel nonmetallic oxidative coupling of alkylthiophene derivatives leading to the corresponding 2,2′-bithiophene derivatives using a combination of a hypervalent iodine(III) reagent, phenyliodine bis(trifluoroacetate) (PIFA), and BF3·Et2O was developed.
SELECTIVE FUNCTIONALIZATION OF 2,2'-BITHIOPHENES
Khor, Eugene,Ng, Siu Choon,Li, Hwee, Chze,Chai, Selenium
, p. 1805 - 1812 (2007/10/02)
The selective functionalization of the 2,2'-bithiophene molecule is described.Selective alkyl substitution at the 3,3'-positions was achieved by sequential bromination of the 3,3' and 5,5' positions followed by debromination at the 5,5'-positions.The resultant 3,3'-dibromo-2,2'-bithiophene was transformed via a Grignard reaction to give a series of 3,3'-dialkyl-2,2'-bithiophenes.Finally, nitration of the active 5,5'positions gave the corresponding 3,3'-dialkyl-5,5'-dinitro-2,2'-bithiophenes.
