122372-64-9Relevant academic research and scientific papers
An extended tetrathiafulvalene redox-ligand incorporating a thiophene spacer
Trippé, Ga?lle,Canevet, David,Le Derf, Franck,Frère, Pierre,Sallé, Marc
, p. 5452 - 5454 (2008)
An extended tetrathiafulvalene derivative incorporating a thiophene spacer and a fused crown-ether unit has been synthesized. This highly delocalized system exhibits remarkable electrochemical recognition properties for Na+ and Ba2+ as shown by cyclic voltammetry in methylene chloride. This result is attributed to the proximity between the guest metal cation and the positive charge of the oxidized ligand, which is located on the central conjugated thiophenic part.
From chains to ladders in co-crystals with 2,3-thiophene-15-crown-5, 2,3-naphtho-15-crown-5, and bis-(18-crown-6)-stilbene constructed by weak hydrogen bonding
Ganin, Eduard V.,Basok, Stepan S.,Yavolovskii, Arkadii A.,Botoshansky, Mark M.,Fonari, Marina S.
, p. 674 - 683 (2011)
For the first time a series of co-crystals of 2,3-thiophene-15-crown-5 1, 2,3-naphtho-15-crown-5 2, bis-(18-crown-6)-stilbene 3 with dithiooxamide a, 1,2,5-oxadiazole-3,4-diamine b, and 3-nitro-1H-1,2,4-triazole c with compositions 1a, 2a, 2b·H2O, 2c, and 3a2 were prepared and their structures were studied by X-ray crystallography. The components in the co-crystals demonstrate the different modes of mutual arrangement and contribution of diverse weak interactions to the final architecture. Infinite chains of the alternating component molecules linked by N-H...O hydrogen bonds characterise the structures of 1a and 2a, whereas in the case of 3a2 formation of the loosely packed ladder-type structure was observed. In 2b·H2O the planar naphtho- and oxadiazole moieties demonstrate their edge-to-face arrangement, while in 2c the partially overlapping naphtho- and triazole moieties provide effective face-to-face π-π stacking interactions. The improved synthetic strategy for 1 and 2 is given.
Synthesis of large ring 3,4-alkylenedioxythiophenes (ADOT) derivatives via Mitsunobu reaction
Xu, Zhaochao,Kang, Joo-Hee,Wang, Fang,Paek, Seung-Min,Hwang, Seong-Ju,Kim, Youngmee,Kim, Sung-Jin,Choy, Jin-Ho,Yoon, Juyoung
supporting information; experimental part, p. 2823 - 2825 (2011/06/21)
Poly(3,4-ethylenedioxythiophene) (PEDOT) stands out for its optimized conductivity, stability, and high degree of transparency which has led to its successful commercialization. These excellent properties of PEDOT are mostly ascribed to the alkylenedioxy bridge across the 3- and 4-positions, and thus much effort has been dedicated to synthesizing 3,4-ethylenedioxythiophene (EDOT) analogs. However, only few homologous compounds were successfully synthesized, such as 3,4-propylenedioxythiophene (PrDOT) or 3,4-(1,4-butylenedioxy)thiophene (BuDOT). In this Letter, we use Mitsunobu reaction to synthesize a series of 3,4-alkylenedioxythiophenes (ADOTs) derivatives with 8- to 16-membered rings. The eight-membered compounds were obtained in high or excellent yield. We also found that the 9- to 16-membered EDOT analogs were obtained in relatively low yield because of the competitive reaction to make dimers. Our method provides an easy way to modify ethylenedioxythiophenes (EDOTs), and these obtained ADOTs compounds are promising building blocks for the synthesis of functional π-conjugated systems used in material chemistry.
Synthesis and Reductive Desulfurization of Crown Ethers Containing Thiophene Subunit
Sone, Tyo,Sato, Kazuaki,Ohba, Yoshihiro
, p. 838 - 844 (2007/10/02)
Crown ethers containing 3,4-thiophenediyl and 3,4-thiophenediylbis(methylene) subunits as a ring constituent were prepared starting from 2,5-bis(ethoxycarbonyl)-3,4-thiophenediol and 2,5-dichloro-3,4-bis(chloromethyl)thiophene, respectively.A Raney nickel desulfurization of the thiophene-containing crown ethers afforded crown ethers having two adjacent side chains, such as a methyl or ethoxycarbonylmethyl group.The extraction ability of these crown ethers towards alkali metal cations was also examined by the solvent extraction method.
