title: The Synthesis of a New Class of Highly Fluorescent Chromones via an Inverse-Demand Hetero-Diels-Alder Reaction.
abstract: A new class of fluorophores has been developed utilizing an inverse-demand hetero-Diels-Alder reaction with silyl enol ethers and substituted 3-formylchromones. These compounds yield blue to green fluorescence with quantum yields up to 73%. They also exhibit good potential for use as fluorescent probes in biological systems, as they are cell membrane permeable with low cytotoxicity.
authors.affiliation: †Department of Chemistry and Biochemistry, Ohio Northern University, Ada, Ohio 45810, United States.
authors.forename: Jake R
authors.initials: JR
authors.lastname: Zimmerman
authors.affiliation: †Department of Chemistry and Biochemistry, Ohio Northern University, Ada, Ohio 45810, United States.
authors.forename: Olivia
authors.initials: O
authors.lastname: Johntony
authors.affiliation: †Department of Chemistry and Biochemistry, Ohio Northern University, Ada, Ohio 45810, United States.
authors.forename: Daniel
authors.initials: D
authors.lastname: Steigerwald
authors.affiliation: †Department of Chemistry and Biochemistry, Ohio Northern University, Ada, Ohio 45810, United States.
authors.forename: Cody
authors.initials: C
authors.lastname: Criss
authors.affiliation: †Department of Chemistry and Biochemistry, Ohio Northern University, Ada, Ohio 45810, United States.
authors.forename: Brian J
authors.initials: BJ
authors.lastname: Myers
authors.affiliation: ‡Department of Pharmaceutical and Biomedical Sciences, Ohio Northern University, Ada, Ohio 45810, United States.
authors.forename: David H
authors.initials: DH
authors.lastname: Kinder
mesh_terms: D002463:Cell Membrane Permeability / Q000187:drug effects; D002867:Chromones / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D061565:Cycloaddition Reaction; D004987:Ethers / Q000737:chemistry; D005453:Fluorescence; D005456:Fluorescent Dyes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D015394:Molecular Structure
chemical_list: D002867:Chromones; D004987:Ethers; D005456:Fluorescent Dyes; C502480:formylchromone