title: Synthesis and optical behaviors of 2-(9-phenanthrenyl)-, 2-(9-anthryl)-, and 2-(1-pyrenyl)-1-alkylimidazole homologues.
abstract: 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.
authors: School of Chemistry and Chemical Engineering, Sun Yat-Sen University, Guangzhou 510275, PR China.
authors: Yun-Nan
authors: YN
authors: Yan
authors: Dan-Yan
authors: DY
authors: Lin
authors: Wen-Long
authors: WL
authors: Pan
authors: Xiu-Ling
authors: XL
authors: Li
authors: Yi-Qian
authors: YQ
authors: Wan
authors: Yu-Liang
authors: YL
authors: Mai
authors: Hua-Can
authors: HC
authors: Song
mesh_terms: 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
chemical_list: D007093:Imidazoles; D010616:Phenanthrenes; D011721:Pyrenes; D014867:Water