title: A self-complementary nucleoside: synthesis, solid-state structure, and fluorescence behavior.
abstract: A novel self-complementary nucleoside ((A)T), featuring two complementary nucleobases linked through an ethynyl group has been synthesized. The rigid aromatic nucleobases provided (A)T with a pale-blue fluorescence. Unlike most fluorescent organic molecules, nucleoside (A)T gives enhanced fluorescence in solid state. It exhibits considerably enhanced fluorescence intensity and a remarkable redshift (ca. 70 nm) in its emission maximum upon an increase in concentration or decrease in temperature as a result of the formation of aggregates stabilized through hydrogen bonding and π-π stacking of well-organized (A) T assemblies; these interactions are also evident in the solid-state structure, determined by X-ray crystallography. DFT calculations supported the preference of such aggregation processes.
authors.affiliation: Department of Chemistry, Division of IBB, Pohang University of Science and Technology, Pohang 790-784, Korea.
authors.forename: Eun-Kyoung
authors.initials: EK
authors.lastname: Bang
authors.forename: Jiyeon
authors.initials: J
authors.lastname: Won
authors.forename: Dohyun
authors.initials: D
authors.lastname: Moon
authors.forename: Jin Yong
authors.initials: JY
authors.lastname: Lee
authors.forename: Byeang Hyean
authors.initials: BH
authors.lastname: Kim
mesh_terms: D018360:Crystallography, X-Ray; D005453:Fluorescence; D008958:Models, Molecular; D009705:Nucleosides / Q000138:chemical synthesis / Q000737:chemistry*
chemical_list: D009705:Nucleosides