α-Terthiophene

Thiotagetin B and tagetannins A and B, new acetylenic thiophene and digalloyl glucose derivatives from Tagetes minuta and evaluation of their in vitro antioxidative and anti-inflammatory activity.[Pubmed:29288025]

Fitoterapia. 2018 Mar;125:78-88.

The three new metabolites: thiotagetin B (2) [(Z)-1''-([2,2'-bithiophen]-5-yl)-8''-chloro-6'',11''-dimethylundeca-6'',10''-die n-2''-yn-9''-one], tagetannin A (9) [3,4-bis-(galloyl-3,5-dimethyl ether)-(alpha/beta)-d-glucopyranose], and tagetannin B (10) [2,3-bis-(galloyl-3,5-dimethyl ether)-(alpha/beta)-d-glucopyranose], along with ecliptal (5-formyl-alpha-terthiophene) (1), 5-(4-hydroxybut-1-ynyl)-2,2'-bithiophene (3), scopoletin (4), p-hydroxybenzoic acid (5), protocatechuic acid methyl ester (6), gallic acid (7), and patuletin 7-O-beta-d-glucoside (8) were isolated from the aerial parts of Tagetes minuta L. (Asteraceae). Their structures were verified by extensive spectroscopic analyses as well as by comparison with literature data. The isolated compounds were evaluated for their antioxidant and anti-inflammatory activities using DPPH and enzyme-linked immunosorbent assays, respectively. Compounds 5-10 possessed the highest antioxidant potential with a scavenging activity (SCA) approximately 74 to 93% of DPPH radicals. Moreover, 5-10 displayed significant anti-inflammatory potential, while 4 showed moderate activity. Compounds 5-10 exhibited significant decreases in NFkappaB p65, TNF-alpha, and IL-6 levels at all tested concentrations.

Gateway state-mediated, long-range tunnelling in molecular wires.[Pubmed:29376529]

Nanoscale. 2018 Feb 8;10(6):3060-3067.

If the factors controlling the decay in single-molecule electrical conductance G with molecular length L could be understood and controlled, then this would be a significant step forward in the design of high-conductance molecular wires. For a wide variety of molecules conducting by phase coherent tunnelling, conductance G decays with length following the relationship G = Ae(-betaL). It is widely accepted that the attenuation coefficient beta is determined by the position of the Fermi energy of the electrodes relative to the energy of frontier orbitals of the molecular bridge, whereas the terminal anchor groups which bind to the molecule to the electrodes contribute to the pre-exponential factor A. We examine this premise for several series of molecules which contain a central conjugated moiety (phenyl, viologen or alpha-terthiophene) connected on either side to alkane chains of varying length, with each end terminated by thiol or thiomethyl anchor groups. In contrast with this expectation, we demonstrate both experimentally and theoretically that additional electronic states located on thiol anchor groups can significantly decrease the value of beta, by giving rise to resonances close to EF through coupling to the bridge moiety. This interplay between the gateway states and their coupling to a central conjugated moiety in the molecular bridges creates a new design strategy for realising higher-transmission molecular wires by taking advantage of the electrode-molecule interface properties.

2,2':5',2''-Terthiophene (α-Terthiophene) is an oligomer of the heterocycle thiophene. 2,2':5',2''-Terthiophene has been employed as building block for the organic semi-conductor polythiophene.

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