327630-34-2Relevant articles and documents
Building blocks for N-type molecular and polymeric electronics. Perfluoroalkyl- versus alkyl-functionalized oligothiophenes (nTs; n = 2-6). Systematic synthesis, spectroscopy, electrochemistry, and solid-state organization
Facchetti, Antonio,Yoon, Myung-Han,Stern, Charlotte L.,Hutchison, Geoffrey R.,Ratner, Mark A.,Marks, Tobin J.
, p. 13480 - 13501 (2004)
The synthesis, comparative physicochemical properties, and solid-state structures of five oligothiophene (nT) series differing in substituent nature and attachment, regiochemistry, and oligothiophene core length (n) are described. These five series include the following 25 compounds: (i) α,ω-diperfluorohexyl-nTs 1 (DFH-nTs, n = 2-6), (ii) β,β′-diperfluorohexyl-nTs 2 (isoDFH-nTs, n = 2-6), (iii) α,ω-dihexyl-nTs 3 (DH-nTs, n = 2-6), (iv) β,β′- dihexyl-nTs 4 (isoDH-nTs, n = 2-6), and (v) unsubstituted oligothiophenes 5 (αnTs, n = 2-6). All new compounds were characterized by elemental analysis, mass spectrometry, and multinuclear NMR spectroscopy. To probe and address quantitatively how the chemistry and regiochemistry of conjugated core substitution affects molecular and solid-state properties, the entire 1-5 series was investigated by differential scanning calorimetry, thermogravimetric analysis, and optical absorption and emission spectroscopies. Single-crystal X-ray diffraction data for several fluorocarbon-substituted oligomers are also presented and compared. The combined analysis of these data indicates that fluorocarbon-substituted nT molecules strongly interact in the condensed state, with unit cell level phase separation between the aromatic core and fluorocarbon chains. Surprisingly, despite these strong intermolecular interactions, high solid-state fluorescence efficiencies are exhibited by the fluorinated derivatives. Insight into the solution molecular geometries and conformational behavior are obtained from analysis of optical and variable-temperature NMR spectra. Finally, cyclic voltammetry data offer a reliable picture of frontier MO energies, which, in combination with DFT computations, provide key information on relationships between oligothiophene substituent effects and electronic response properties.
A new method of using supercritical carbon dioxide as a green solvent for synthesis and purification of 5,5?-bis(tridecafluorohexyl)-2,2′:5′,2″:5″,2?-quaterthiophene, which is one of n-type organic semiconducting materials
Hirase, Ryuji,Honda, Koji,Ishihara, Mari,Yoshioka, Hideki,Monobe, Hirosato
, p. 469 - 472 (2018/01/04)
We have investigated synthesis as well as purification of 5,5?-bis(tridecafluorohexyl)-2,2′:5′,2″:5″,2?-quaterthiophene (BFH-4 T, n-type organic semiconducting material) using supercritical carbon dioxide (scCO2) as a green solvent. BFH-4T was obtained in good selectivity and high yield by TDAE/PdCl2-catalyzed reductive coupling reaction of 5-bromo-5′-(tridecafluorohexyl)-2,2′-bithiophene in scCO2. We have also successfully established purification of the reaction mixture by passing scCO2 in the reaction vessel. The product was yellow powder of BFH-4T with purity of more than 99% and Pd catalyst was not contained.
Tuning the semiconducting properties of sexithiophene by α,ω-substitution - α,ω-diperfluorohexylsexithiophene: The first n-type sexithiophene for thin-film transistors
Facchetti, Antonio,Deng, Yvonne,Wang, Anchuan,Koide, Yoshihiro,Sirringhaus, Henning,Marks, Tobin J.,Friend, Richard H.
, p. 4547 - 4551 (2007/10/03)
The first substituent-induced "flip" from p- to n-type conductivity as well as enhanced thermal stability and volatility are found for fluorocarbon-functionalized sexithiophene 1 (relative to the fluorine free analogues 2 and 3). Evaporated films of 1 beh
