Synthesis and optical behaviors of 2-(9-phenanthrenyl)-, 2-(9-anthryl)-, and 2-(1-pyrenyl)-1-alkylimidazole homologues.
Eight 2-(9-phenanthrenyl)-, 2-(9-anthryl)- and 2-(1-pyrenyl)-1-alkyl-benzimidazole compounds, three 2-(9-anthryl)-1-alkylphenanthroimidazole compounds and five 4,5-diphenyl-1-alkyl-2-(9-anthryl)imidazole compounds were synthesized by alkylation reactions of the corresponding benzimidazole, phenanthroimidazole or imidazole compounds. 2-(10-Bromo-9-anthryl)-1-alkyl-benzimidazole compounds were prepared by bromination reaction of 2-(9-anthryl)-1-alkylbenzimidazole compounds. All the synthesized compounds were characterized by elemental analysis, (1)H NMR, (13)C NMR, MS or HRMS; their absorption coefficients (epsilon), maximum absorption lambda(amax), fluorescence emission maximum lambda(em), Stokes shifts and fluorescence quantum yields (Phi(F)) in ethyl acetate were determined; their fluorescent lifetimes (T(1) and T(2)) were measured in ethyl acetate and in solid state, respectively. The crystal structure of 2-(9-anthryl)-1-n-butyl-4,5-diphenylimidazole (12a) was determined to be triclinic, space group P-1 types, using single crystal X-ray crystallography technique. The results showed that these compounds exhibited moderate fluorescence-emission abilities and higher solubility in most organic solvents than their corresponding starting materials. The relationships between the optical behaviors and structures for these compounds were discussed.
Yan
Yun-Nan
YN
School of Chemistry and Chemical Engineering, Sun Yat-Sen University, Guangzhou 510275, PR China.
Lin
Dan-Yan
DY
Pan
Wen-Long
WL
Li
Xiu-Ling
XL
Wan
Yi-Qian
YQ
Mai
Yu-Liang
YL
Song
Hua-Can
HC
D000478:Alkylation; D018360:Crystallography, X-Ray; D007093:Imidazoles / Q000138:chemical synthesis / Q000737:chemistry*; D008954:Models, Biological; D008958:Models, Molecular; D015394:Molecular Structure; D055095:Optics and Photonics; D010616:Phenanthrenes / Q000138:chemical synthesis / Q000737:chemistry*; D011721:Pyrenes / Q000138:chemical synthesis / Q000737:chemistry*; D012995:Solubility; D013056:Spectrophotometry, Ultraviolet; D014867:Water / Q000737:chemistry / Q000494:pharmacology
D007093:Imidazoles; D010616:Phenanthrenes; D011721:Pyrenes; D014867:Water