title: Acridine-based macrocyclic fluorescent sensors: self-assembly behavior characterized by crystal structures and a tunable bathochromic-shift in emission induced by H2PO4(-)via adjusting the ring size and rigidity.
abstract: In this paper, a series of novel acridine derived bisbenzimidazolium macrocyclic fluorescent sensors were designed and synthesized. X-ray crystal structures demonstrated the self-assembly behavior of these cyclophanes in the solid state driven by hydrogen bond and π-π interactions. Anion binding studies of these sensors revealed a significant effect of the macrocyclic size and rigidity for H2PO4(-) sensing via the obvious turn-on as well as bathochromic-shift in fluorescence emission. Different cavity size or rigidity of the sensors showed different bathochromic-shifts (from 36 to 126 nm) in fluorescence emission induced by H2PO4(-), which resulted in significant color changes of fluorescence from blue to orange red, orange, green and blue-green respectively. The unique fluorescence response toward H2PO4(-) may be attributed to H2PO4(-)-induced assembly of sensors forming the excimer between two acridine rings to a different extent.
authors.affiliation: Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Department of Chemistry, East China Normal University, Shanghai, 200062, P R China.
authors.forename: Dawei
authors.initials: D
authors.lastname: Zhang
authors.forename: Xiaozhi
authors.initials: X
authors.lastname: Jiang
authors.forename: Haiqiang
authors.initials: H
authors.lastname: Yang
authors.forename: Alexandre
authors.initials: A
authors.lastname: Martinez
authors.forename: Meiyuan
authors.initials: M
authors.lastname: Feng
authors.forename: Zhiyun
authors.initials: Z
authors.lastname: Dong
authors.forename: Guohua
authors.initials: G
authors.lastname: Gao
mesh_terms: D000166:Acridines / Q000737:chemistry*; D018360:Crystallography, X-Ray; D005456:Fluorescent Dyes / Q000138:chemical synthesis* / Q000737:chemistry; D047028:Macrocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D010316:Particle Size; D010710:Phosphates / Q000737:chemistry*; D013050:Spectrometry, Fluorescence
chemical_list: D000166:Acridines; D005456:Fluorescent Dyes; D047028:Macrocyclic Compounds; D010710:Phosphates