title: Electrochemically active cross-linking reaction for fluorescent labeling of aliphatic alkenes.
abstract: Although cross-linking reactions serve as a valuable tool for the integration of two or more functionalities or properties, the application of electrochemical synthesis to cross-linking reactions is restricted due to the difficulty of mass transfer. Thus, the primary purpose of this research is to explore electrochemical cross-linking systems to construct a fluorescent probe, triggered by the formation of a covalent linkage. The second purpose is to apply the probe to insoluble targets. Towards these goals, a combination of electrochemically active phenol derivatives and aliphatic alkenes were employed to form polycyclic compounds. Several of the dihydrobenzofuran derivatives formed through [3+2] cyclization reactions exhibited fluorescence. Furthermore, this approach allowed the effective modification of alkene-modified silica gel with electrochemically active species, which enables the construction of fluorescent probes that are triggered by C-C bond formation.
authors.affiliation: Laboratory of Bio-organic Chemistry, Tokyo University of Agriculture and Technology, 3-5-8 Saiwai-cho, Fuchu, Tokyo 183-8509, Japan.
authors.forename: Shokaku
authors.initials: S
authors.lastname: Kim
authors.forename: Kumi
authors.initials: K
authors.lastname: Hirose
authors.forename: Jumpei
authors.initials: J
authors.lastname: Uematsu
authors.forename: Yuzuru
authors.initials: Y
authors.lastname: Mikami
authors.forename: Kazuhiro
authors.initials: K
authors.lastname: Chiba
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D020650:Combinatorial Chemistry Techniques; D003432:Cross-Linking Reagents / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D004563:Electrochemistry; D005456:Fluorescent Dyes / Q000138:chemical synthesis* / Q000737:chemistry; D049449:Luminescence; D015394:Molecular Structure
chemical_list: D000475:Alkenes; D003432:Cross-Linking Reagents; D005456:Fluorescent Dyes