title: Synthesis and Characterization of Far-Red/NIR-Fluorescent BODIPY Dyes, Solid-State Fluorescence, and Application as Fluorescent Tags Attached to Carbon Nano-onions.
abstract: A series of π-extended distyryl-substituted boron dipyrromethene (BODIPY) derivatives with intense far-red/near-infrared (NIR) fluorescence was synthesized and characterized, with a view to enhance the dye's performance for fluorescence labeling. An enhanced brightness was achieved by the introduction of two methyl substituents in the meso positions on the phenyl group of the BODIPY molecule; these substituents resulted in increased structural rigidity. Solid-state fluorescence was observed for one of the distyryl-substituted BODIPY derivatives. The introduction of a terminal bromo substituent allows for the subsequent immobilization of the BODIPY fluorophore on the surface of carbon nano-onions (CNOs), which leads to potential imaging agents for biological and biomedical applications. The far-red/NIR-fluorescent CNO nanoparticles were characterized by absorption, fluorescence, and Raman spectroscopies, as well as by thermogravimetric analysis, dynamic light scattering, high-resolution transmission electron microscopy, and confocal microscopy.
authors.affiliation: Istituto Italiano di Tecnologia (IIT), Nano Carbon Materials, Via Morego 30, 16163 Genova (Italy).
authors.forename: Juergen
authors.initials: J
authors.lastname: Bartelmess
authors.affiliation: Istituto Italiano di Tecnologia (IIT), Nano Carbon Materials, Via Morego 30, 16163 Genova (Italy).
authors.forename: Michele
authors.initials: M
authors.lastname: Baldrighi
authors.affiliation: Istituto Italiano di Tecnologia (IIT), Center for Nano Science and Technology, Via G. Pascoli 70/3, 20133 Milano (Italy).|Department of Chemistry, Material and Chemical Engineering, Politecnico di Milano, Piazza Leonardo Da Vinci, 20133 Milano (Italy).
authors.forename: Valentina
authors.initials: V
authors.lastname: Nardone
authors.affiliation: Istituto Italiano di Tecnologia (IIT), Center for Nano Science and Technology, Via G. Pascoli 70/3, 20133 Milano (Italy).
authors.forename: Emilio
authors.initials: E
authors.lastname: Parisini
authors.affiliation: Department of Chemistry, University of Texas at El Paso, 500 W. University Ave., El Paso, TX 79968 (USA).
authors.forename: David
authors.initials: D
authors.lastname: Buck
authors.affiliation: Department of Chemistry, University of Texas at El Paso, 500 W. University Ave., El Paso, TX 79968 (USA).
authors.forename: Luis
authors.initials: L
authors.lastname: Echegoyen
authors.affiliation: Istituto Italiano di Tecnologia (IIT), Nano Carbon Materials, Via Morego 30, 16163 Genova (Italy). silvia.giordani@iit.it.
authors.forename: Silvia
authors.initials: S
authors.lastname: Giordani
keywords: carbon; fluorescent probes; imaging agents; nanostructures; solid-state fluorescence