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A series of promising candidates for n-type semiconductors, which were based on pyrene-thiophene backbone 1,6-, 1,8- and mono-substituted with cyano group and dicyanovinylene moieties, were synthesized. The compounds were characterized… Click to show full abstract
A series of promising candidates for n-type semiconductors, which were based on pyrene-thiophene backbone 1,6-, 1,8- and mono-substituted with cyano group and dicyanovinylene moieties, were synthesized. The compounds were characterized with nuclear magnetic resonance (NMR), elemental analysis, UV-vis, photoluminescence (PL), thermal gravimetric analysis (TGA), differential scanning calorimetry (DSC), cyclic voltametry (CV) and Density functional theory (DFT) calculations. The effects of substitution position and substituent type on molecular properties were studied in detail. We found that the dicyanovinylene substitution enhanced the coplanarity of the π-conjugated systems compared with cyano substitution. The lowest unoccupied molecular orbital (LUMO) energy level was located deeply, and one of them had LUMO of below -4.00 eV, indicating that they may be promising candidates of n-type semiconductors.
Journal Title: Asian Journal of Organic Chemistry
Year Published: 2017
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