Takaya Matsuo, Kohsuke Kawabata and Kazuo Takimiya
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引用次数: 0
Abstract
Quinoidal π-extended dipyranylidene derivatives, 2,2′,6,6′-tetraphenyl-4,4′-(cyclohexa-1,4-diene-3,6-diylidene)dipyran (DP8) and its tetrakis(dimethylamino) derivative (DP9), were newly synthesized and characterized. DP8, with the HOMO energy level (EHOMO) of −4.2 eV, was isolated as a stable compound, whereas DP9, with a very high-lying EHOMO of −3.9 eV, was unstable under ambient air conditions. Nevertheless, they were well characterized by means of single-crystal X-ray analysis. Based on the bond lengths and theoretical calculations, it was concluded that they mainly have a quinoidal character in the crystalline state. DP9, with the highest EHOMO among the dipyranylidene-based n-type dopants, acted as an efficient dopant to polybenzimidazobenzophenanthroline (BBL) with a low-lying LUMO energy level (ELUMO) of −4.3 eV and to N2200 with an ELUMO of −3.8 eV. Although the ambient stability of DP9 was still an issue, the quinoidal π-extension is an efficient strategy to develop n-type dopants with “Weitz type” molecules.
期刊介绍:
Organic Chemistry Frontiers is an esteemed journal that publishes high-quality research across the field of organic chemistry. It places a significant emphasis on studies that contribute substantially to the field by introducing new or significantly improved protocols and methodologies. The journal covers a wide array of topics which include, but are not limited to, organic synthesis, the development of synthetic methodologies, catalysis, natural products, functional organic materials, supramolecular and macromolecular chemistry, as well as physical and computational organic chemistry.