Development of excellent long-wavelength BODIPY laser dyes with a strategy that combines extending π-conjugation and tuning ICT effect

• Published in: Physical chemistry chemical physics : PCCP Vol. 13; no. 28; p. 13026
• Main Authors: Zhang, Dakui, Martín, Virginia, García-Moreno, Inmaculada, Costela, Angel, Pérez-Ojeda, M Eugenia, Xiao, Yi
• Format: Journal Article
• Language: English
• Published: England 28-07-2011
• Subjects: Acetates - chemistry; Acetone - chemistry; Acetonitriles - chemistry; Boron Compounds - chemistry; Cell Line, Tumor; Cell Survival - drug effects; Cytoplasm - metabolism; Electrochemistry; Ethanol - chemistry; Fluorescent Dyes - chemical synthesis; Fluorescent Dyes - chemistry; Fluorescent Dyes - metabolism; Fluorescent Dyes - pharmacology; Hexanes - chemistry; Humans; Lasers, Dye; Lasers, Solid-State; Methanol - chemistry; Methylene Chloride - chemistry; Models, Molecular; Molecular Structure; Optics and Photonics; Photolysis - radiation effects; Quantum Theory; Solvents - chemistry; Spectrometry, Fluorescence; Spectrophotometry; Trifluoroethanol - chemistry
• ISSN: 1463-9084
• DOI: 10.1039/c1cp21038f

By comparison and combination of two strategies, extending π-conjugation and tuning Intramolecular Charge Transfer (ICT) effect, new long-wavelength BODIPY dyes have been efficiently synthesized. The new chromophores exhibit good optical properties: high fluorescence quantum yields, exceptionally large molar extinction coefficients, narrow red-emission bands, and relatively large Stokes shifts etc., in polar or apolar solvents. Besides, the new dyes, under transversal pumping at 532 nm, exhibit highly efficient and stable laser emission tunable from the green to NIR spectral region (570-725 nm). Moreover, one of these new BODIPY derivatives shows cell membrane permeability and bright intracellular red fluorescence. These advantageous characteristics assure the potential of these dyes for biophotonic applications.