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Synthesis of Bis([2,2'-bithiophen]-5-yl)-Substituted Oligothiadiazoles: Effect of the Number of Acceptor Units on Electrochemical and Spectroscopic Properties

Synthesis of Bis([2,2'-bithiophen]-5-yl)-Substituted Oligothiadiazoles: Effect of the Number of Acceptor Units on Electrochemical and Spectroscopic Properties

Anastasia S Kostyuchenko, Aleksandra Kurowska, Pawel Zassowski, Tatyana Yu Zheleznova, Evgeny B Ulyankin, Wojciech Domagala, Adam Pron, Alexander S Fisyuk

J Org Chem. 2019 Aug 16;84(16):10040-10049.

PMID: 31315394

Abstract:

1,3,4-Thiadiazole, 2,2'-bi(1,3,4-thiadiazole), 2,2':5',2″-ter(1,3,4-thiadiazole), and 2,2':5',2″:5″,2‴-quater(1,3,4-thiadiazole) symmetrically disubstituted with 3-alkyl-(2,2'-bithiophen)-5-yl were synthesized by new procedures using readily available ethyl 3-alkyl-(2,2'-bithiophene)-5-carboxylate as a convenient substrate. These new compounds with a fixed number of donor rings and increasing number of acceptor rings showed very interesting, tunable redox properties. In particular, they exhibited electron affinities (EAs) ranging from -3.06 to -3.83 eV, reaching EA values desired for air-operating n-type organic semiconductors. Their electrochemically determined ionization potentials were only moderately dependent on the number of thiadiazole rings, varying from 5.83 to 6.01 eV. Emission spectra of these compounds could also be tuned in a wide range (from 470 to 600 nm). Spectroscopic and electrochemical data were confirmed by density functional theory calculations demonstrating full consistency.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP125143535	3,3′,5,5′-Tetrabromo-2,2′-bithiophene		125143-53-5	Price
AP327630342	5-Perfluorohexyl-2,2′-bithiophene		327630-34-2	Price

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