Synthesis and characterization of solution processable 6,11-dialkynyl substituted indeno[1,2-b]anthracenes

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• 作者：Baris Yucel ; Kadem Meral ; Duygu Ekinci ; G眉l艧ah Yaman Uzuno臒lu ; Nurcan 艦enyurt T眉z眉n ; S眉heyla 脰zbey ; Canan Kazak ; Yavuz Ozdemir ; Bahar Sanli ; G眉lru Kay谋k ; Metin Da臒deviren
• 关键词：Anthracene ; Benzocyclobutenedione ; Indene ; Indenoanthracene ; Indenoanthraquinone ; Solution processable
• 刊名：Dyes and Pigments
• 出版年：January, 2014
• 年：2014
• 卷：100
• 期：Complete
• 页码：104-117
• 全文大小：1867 K

文摘

Twelve indene-fused dialkynyl substituted anthracene derivatives (indenoanthracenes) were synthesized and their optical, electrochemical and thermal properties were described. These small molecules possess high quantum yields, thermal and photoxidative stabilities, and solubility in common organic solvents. Indenoanthracenes (57-92%) were prepared in two steps from four different indenoanthraquinones obtained via a highly selective and practical benzocyclobutendione based methodology. The photophysical properties of indenoanthracenes were investigated by UV-vis and fluorescence spectroscopies. From spectroscopic data of indenoanthracenes, quantum yields (桅_茠, 0.28-0.71) and optical HOMO-LUMO energy gaps were determined. Electrochemistry of indenoanthracenes was studied and electrochemical HOMO-LUMO energy gaps were also determined from the onset oxidation and reduction potentials. Density functional theory calculations were performed to obtain the geometry optimized structures and HOMO-LUMO energy levels. Fluorenylethynyl substituted indenoanthracene was employed as an emitting layer in a solution processed OLED device and the maximum current efficiency and luminance were found to be 1.02聽cd/A and 1284聽cd/m², respectively.