Alkyl chain length dependent morphology and emission properties of the organic micromaterials based on fluorinated quinacridone derivatives.
The fluorinated quinacridone derivatives N,N'-dialkyl-2,9-difluoroquinacridone (Cn-DFQA, n = 4, 8, 10, 16) with different alkyl chains were used as building blocks to assemble luminescent micromaterials. It was demonstrated that the morphology and emission of the Cn-DFQA-based micromaterials strongly depended on their alkyl chain length. C4-DFQA and C8-DFQA showed stronger tendency to form 1-D microstructures, while C10-DFQA and C16-DFQA displayed the aggregation properties to form diamond and hexagonal platelike microcrystals, respectively. The photoluminescent (PL) spectra of Cn-DFQA (n = 4, 8, 10, 16) in THF dilute solutions displayed approximate profiles with a sharp emission peak at 533 nm and a shoulder at 573 nm, while the PL spectra of the Cn-DFQA-based micromaterials exhibited obviously red-shift emission bands at 622 nm for C4-DFQA, 627 nm for C8-DFQA, 614 nm for C10-DFQA, and 613 nm for C16-DFQA, respectively. The single-crystal X-ray structures of four Cn-DFQA compounds have been studied. In the C4-DFQA and C8-DFQA single crystals, there are 1-D molecular columns based on the intermolecular pi...pi and hydrogen bonding interactions. In the single crystals of C10-DFQA and C16-DFQA, the molecules assembled into 2-D molecular sheets based on the hydrogen bonds and C-H...pi interactions. The molecular packing structures provide a reasonable explanation for the alkyl chain length dependent morphologies and emission properties of fluorinated quinacridone micromaterials.
State Key Laboratory of Supramolecular Structure and Materials, College of Chemistry, Jilin University, Changchun 130012, PR China.
Yunfeng
Y
Zhao
Xiaoyue
X
Mu
Chunxiao
C
Bao
Yan
Y
Fan
Jingying
J
Zhang
Yue
Y
Wang