Synthesis and electronic properties of pentacene derivatives as promising n-type semiconductor candidates

Two pentacene derivatives 1 and 2 were synthesized from the Diels-Alder reactions of furan derivatives with 1,4-benzoquinone. They were characterized by the methods of ¹H - nuclear magnetic resonance spectroscopy (¹H-NMR), matrix-assisted laser desorption/ionization time of flight mass spectrometry (MALDI-TOF MS), ultraviolet and visible spectrophotometry (UV-VIS), photoluminescence (PL) spectrometry and cyclic voltammetry (CV). The energy gaps of 1 and 2, taken directly from spectroscopic measurements, are broad as 2.72 and 2.46 eV, leading to blue and greenish blue photoluminescence, respectively. The LUMO and HOMO energy levels are -2.77 and -5.49 eV for 1, and -2.91 and -5.37 eV for 2, respectively. The low energy levels make both 1 and 2 good air-stabilities and promi sing n-type semiconductor candidates for use in organic electronics.