Journal of Organic Chemistry 2009-10-02

Dicyanovinyl heterotetracenes: synthesis, solid-state structures, and photophysical properties.

Chunyan Du, Jianming Chen, Yunlong Guo, Kun Lu, Shanghui Ye, Jian Zheng, Yunqi Liu, Zhigang Shuai, Gui Yu

Index: J. Org. Chem. 74(19) , 7322-7, (2009)

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Abstract

Two asymmetrically substituted dicyanovinyl heterotetracenes are synthesized and characterized. Single-crystal X-ray diffractions indicate both intermolecular hydrogen bonds and pi-stacking existing in the solid-state structures. The solvatochromic behaviors of the two heterotetracenes were investigated in a variety of solvents. Both experimental and computational results suggest that the two heterotetracenes have low-lying lowest unoccupied molecular orbitals and thus may be potential n-type or bipolar organic semiconductors for organic electronics.