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

Abstract

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 aggrega...