Synthesis and Divergent Electronic Properties of Two Ring-Fused Derivatives of 9,10-Diphenylanthracene

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• 作者：M. Rajeswara Rao ; Hayden T. Black ; Dmitrii F. Perepichka
• 刊名：Organic Letters
• 出版年：2015
• 出版时间：September 4, 2015
• 年：2015
• 卷：17
• 期：17
• 页码：4224-4227
• 全文大小：347K
• ISSN：1523-7052

文摘

Two new contorted polycyclic aromatic hydrocarbons (PAHs) 1 and 2 were synthesized by acid-catalyzed benzannulation of a substituted anthracene. The isomers reveal dissimilar photophysical and redox properties with 2 having a much smaller HOMO鈥揕UMO gap than 1. In the solid state, 2 packs in a unique two-dimensional herringbone motif that gives rise to efficient ambipolar charge transport in OFET devices, a feature not previously observed in contorted PAHs. On the other hand, 1 packs in one-dimensional dimerized 蟺-stacks and displays insulating properties.