title: Fluorescent 3-methylene-2,3-dihydrochalcogenophenes incorporated in a rigid dibenzobarrelene skeleton.
abstract: The fluorescent 3-methylene-2,3-dihydroselenophene derivative (Φ(F) = 0.86 in CH(2)Cl(2)) incorporated in a dibenzobarrelene skeleton was synthesized by the reaction of a four-membered selenaplatinacycle with dimethyl acetylenedicarboxylate (DMAD) or reaction of bis(dibenzobarrelenyl) diselenide with DMAD in the presence of Pd(PPh(3))(4) and PPh(3). A fluorescent sulfur homologue (Φ(F) = 1.0 in CH(2)Cl(2)) was also synthesized by the reaction of bis(dibenzobarrelenyl) disulfide with DMAD in the presence of Pd(PPh(3))(4). Selected chemical transformations of these diesters were also investigated.
authors.affiliation: Department of Chemistry, Graduate School of Science and Engineering, Saitama University, Shimo-okubo 255, Saitama 338-8570, Japan. ishiiaki@chem.saitama-u.ac.jp
authors.forename: Akihiko
authors.initials: A
authors.lastname: Ishii
authors.forename: Yuki
authors.initials: Y
authors.lastname: Yamaguchi
authors.forename: Norio
authors.initials: N
authors.lastname: Nakata
mesh_terms: D001555:Benzene Derivatives / Q000138:chemical synthesis* / Q000737:chemistry; D018360:Crystallography, X-Ray; D005456:Fluorescent Dyes / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D016566:Organoselenium Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013876:Thiophenes / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D001555:Benzene Derivatives; D005456:Fluorescent Dyes; D016566:Organoselenium Compounds; D013876:Thiophenes