The unsymmetric dithieno[3,2-b:3',4'-d]thiophene (ts-DTT) was efficiently synthesized, and two novel heptathienoacenes with linear and bull's horn shapes were designed and prepared via different ring cyclization connection manners. All intermediates and aimed heptathienoacenes were fully characterized by (1)H NMR, (13)C NMR, and HRMS. Their UV-vis absorption behavior, fluorescence, and electrochemical properties are characterized. In addition, DFT quantum calculation was employed to further understand the electron distribution and the origin of the absorption bands.
SummaryIn this paper, the ring-opening reaction of 2,5-dioctyldithieno[2,3-b:3',2'-d]thiophene with aryllithium in THF at low temperature to generate 2'-arylthio-3,3'-bithiophene-2-carbaldehydes is studied. Nine examples are explored and all the products are characterized by 1H NMR, 13C NMR and HRMS. The relative relationship between the structures of aryl groups and the efficiency of ring-opening reactions are discussed.
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