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Synthesis and Properties of Acridone Oligomers
Author(s) -
Liu Renfei,
Zhu Guanxing,
Ji Yongxin,
Zhang Gang
Publication year - 2019
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201900511
Subject(s) - acridone , oligomer , chemistry , borylation , photochemistry , absorption (acoustics) , carbocation , homo/lumo , fluorescence , stereochemistry , polymer chemistry , organic chemistry , molecule , materials science , alkyl , physics , quantum mechanics , aryl , composite material
Length‐defined 2,7‐acridone oligomers were synthesized via a sequence of bromination, borylation and Suzuki–Miyaura cross‐coupling reaction. Both the single crystal structure analysis and the theoretical calculations demonstrate that the anti conformation is favored in the oligomer. The relationship of the properties and the number of acridone units in the oligomer was investigated. The UV/Vis absorption and fluorescence spectroscopy reveal that the absorption and emission of oligomers are red‐shifted and energy gaps narrow with the increase of acridone moieties, as well as a decline in the radiative decay rate. Cyclic voltammetry measurements and theoretical calculations elucidate that the quantity of acridone in the oligomer plays a greater effect on the HOMO energy levels than on the LUMO ones.