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Regioisomerically Pure 1,7‐Dibromo‐Substituted Perylene Bisimide Dyes: Efficient Synthesis, Separation, and Characterization
Author(s) -
Ma Jiajun,
Yin Leicheng,
Zou Gang,
Zhang Qijin
Publication year - 2015
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.201500206
Subject(s) - ethylamine , chemistry , perylene , structural isomer , fluoranthene , spectroscopy , recrystallization (geology) , nuclear magnetic resonance spectroscopy , pyrene , photochemistry , organic chemistry , molecule , paleontology , physics , quantum mechanics , biology
1,7‐Dibromo‐substituted perylene bisimides have been obtained in yields of at least 60 % in regioisomerically pure form by treating the commonly used dibromoperylene‐3,4,9,10‐tetracarboxylic dianhydride with 2‐(diethylamino)ethylamine or 2‐(dimethylamino)ethylamine and then separating the 1,7‐isomer from the regioisomeric mixtures by conventional column chromatography and without recrystallization. The individual regioisomers were fully characterized by 1 H NMR spectroscopy and HRMS. The signals of the protons located in the aromatic region and neighboring the imide nitrogen atom were utilized to confirm the chemical structures of the isomers. The 1,7‐dibromo isomer obtained with 2‐(dimethylamino)ethylamine in such a convenient and efficient way was further used to prepare 1,7‐disubstituted perylene bisimide derivatives by saponification, amidation, and then bay‐position substitution reactions. These compounds exhibited a significant redshift and broadening of their absorption and emission in optical spectroscopy analysis.