Substitution Position Directing the Molecular Packing, Electronic Structure, and Aggregate Emission Property of Bis[2-(9-anthracenyl)vinyl]benzene System

• Published in: Journal of physical chemistry. C Vol. 116; no. 10; pp. 6401 - 6408
• Main Authors: Li, Ye-Xin, Chen, Zhi, Cui, Yu, Xia, Guang-Ming, Yang, Xiao-Feng
• Format: Journal Article
• Language: English
• Published: Columbus, OH American Chemical Society 15.03.2012
• Subjects: Applied sciences; Condensed matter: electronic structure, electrical, magnetic, and optical properties; Electronics; Exact sciences and technology; Molecular electronics, nanoelectronics; Optical properties and condensed-matter spectroscopy and other interactions of matter with particles and radiation; Optical properties of bulk materials and thin films; Photoluminescence; Physics; Semiconductor electronics. Microelectronics. Optoelectronics. Solid state devices; Stacking sequence; Molecular structure; Fluorescence; Zigzag structure; Columnar structure; Aggregation; Solid state; Molecular electronics; Electronic structure; Benzene; Optical properties; Photoelectronic properties; Aggregate
• ISSN: 1932-7447; 1932-7455
• DOI: 10.1021/jp211364m

Because of the difference in substitution position, compounds 1,2-bis[2-(9-anthracenyl)vinyl]benzene (1,2-BAVB), 1,3-bis[2-(9-anthracenyl)vinyl]benzene (1,3-BAVB), and 1,4-bis[2-(9-anthracenyl)vinyl]benzene (1,4-BAVB) display different crystal packing and optical property. 1,4-BAVB molecules pack into zigzag structure. The π-electrons are averagely distributed on the whole backbone though the molecule adopts a twisted structure. Compounds 1,2-BAVB and 1,3-BAVB have a column-like structure, and the π-electrons are mainly confined on the anthracene units. Obvious π···π interactions exist in the aggregates of 1,3-BAVB and 1,4-BAVB. The crystal packing and electronic structure exert dramatic influence on the photophysical property. Compound 1,4-BAVB is hardly emissive. Compound 1,3-BAVB is highly emissive in solution but quenched in the solid state. However, compound 1,2-BAVB displays an aggregation-induced emission behavior and an excimer-related fluorescence in solution. The relationship between the aggregate packing, electronic structure, and photophysical property was studied.