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For their great structural versatility, thiophene-based π-conjugated systems have been widely exploited in the preparation of low band gap materials. Here, we report the synthesis of a highly conjugated tetrathiophene system, namely 1,4-di([2,2′-bithiophen]-3-yl)buta-1,3-diyne (<b>1</b>), that presents two bithiophene units connected at position 3 by a butadiynylene spacer. Single-crystal X-ray diffraction (SC-XRD) analysis elucidated the structure of <b>1</b>, confirming the planarity of the molecule. The molecule was then electropolymerized onto the surface of a gold-coated piezoelectric quartz crystal, showing a high reactivity that is ascribable to the extended conjugation. The frontier molecular orbital energies of <b>1</b> were obtained via DFT optimization performed on the crystal structure-derived molecular geometry. Finally, DFT was also used to estimate the polymer band gap.