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• 65016-62-8 3-octylthiophene 

Relevant academic research and scientific papers

Effect of chain extension on the electrochemical and electronic properties of π-conjugated soluble thienylenevinylene oligomers

Thienylenevinylene oligomers (nTVs) containing up to 10 thiophene rings and bearing solubilizing hexyl groups at the α-position of the end thiophene rings or octyl or dibutyl chains at the 3-position or the 3- and 4-positions of the thiophene rings have been synthesized by a combination of formylation reaction, Wittig-Horner olefination, and McMurry dimerization. Owing to the good solubility imparted by alkyl chains, the electrochemical behavior of nTVs has been analyzed for the first time. Chain extension leads to;a negative shift of the peak potentials corresponding to the formation of the cation radical and dication and to a decrease of their difference. For the octamers the dication is formed directly through a two-electron transfer while the system can be reversibly charged up to the tetracationic state. Electronic absorption spectra show the expected bathochromic shift of λ(max) and decrease of the HOMOLUMO gap with extension of the conjugation length. Thus, solution-cast films of octamers exhibit band-gap values electrochemical and optical data to infinite chain length suggests that the oxidation potential and:intrinsic band gap of a defect-free PTV could be significantly smaller than the present experimental values.

Electronic properties of thienylene vinylene oligomers: Synthesis and theoretical study

(E)-1,2-bis(2-thienyl)vinylene (TV), (E)-1,2-bis (3-octyl-2-thienyl) vinylene (TOV), (E)-1,2-bis(3-(2-ethylhexyl)-2-thienyl)vinylene (T2EHV), and (E)-1,2-bis-[2,2'-bithienyl] vinylene (BTV) have been synthesized by a combination of formylation reaction and Mc Murry dimerization. UV-Vis spectra of BTV showed the longest wavelength absorption, TOV and T2EHV showed a bathochromic shift to the red compared with TV, due to an increment of delocalization of the conjugated p-system as the result of the weakening of the carbon-carbon double bonds of the thienyl rings due to the substitution of one hydrogen by the alkyl group. Based on optical data, the effect of linear and branched alkyl chain and extension of conjugation length on the electronic properties is discussed. 1H, 13C-NMR, UV-Visible, Fluorescence data are discussed and theoretical DFT and TD-DFT calculations of ground state and excited states have been also considered in the analysis and explanation of results. Springer Science+Business Media, LLC 2012.

Soluble thienylenevinylene oligomers end-capped with 1,3-dithiole-2-ylidene groups

The synthesis of thienylenevinylene oligomers end-capped with 1,3-dithiole-2-ylidene is described. CV analysis shows that these compounds can be oxidized up to their tetracationic state within a narrow potential window.