Synthesis and Spectroscopy of Benzylamine-Substituted BODIPYs for Bioimaging
Consuelo Ripoll
Department of Physical Chemistry, Faculty of Pharmacy, University of Granada, Campus Cartuja, 18071 Granada, Spain
Search for more papers by this authorCheng Cheng
The Key Laboratory of Functional Molecular Solids, Ministry of Education, School of Chemistry and Materials Science, Anhui Normal University, 241000 Wuhu, China
Search for more papers by this authorEmilio Garcia-Fernandez
Department of Physical Chemistry, Faculty of Pharmacy, University of Granada, Campus Cartuja, 18071 Granada, Spain
Search for more papers by this authorJin Li
The Key Laboratory of Functional Molecular Solids, Ministry of Education, School of Chemistry and Materials Science, Anhui Normal University, 241000 Wuhu, China
Search for more papers by this authorAngel Orte
Department of Physical Chemistry, Faculty of Pharmacy, University of Granada, Campus Cartuja, 18071 Granada, Spain
Search for more papers by this authorHainam Do
Department of Chemical and Environmental Engineering, University of Nottingham Ningbo China, 199 Taikang East Road, 315100 Ningbo, China
Search for more papers by this authorCorresponding Author
Lijuan Jiao
The Key Laboratory of Functional Molecular Solids, Ministry of Education, School of Chemistry and Materials Science, Anhui Normal University, 241000 Wuhu, China
The Key Laboratory of Functional Molecular Solids, Ministry of Education, School of Chemistry and Materials Science, Anhui Normal University, Wuhu 241000, China
E-mail: [email protected]
Search for more papers by this authorCorresponding Author
David Robinson
Department of Chemistry and Forensics, Nottingham Trent University, Clifton Lane, Nottingham, United Kingdom
The Key Laboratory of Functional Molecular Solids, Ministry of Education, School of Chemistry and Materials Science, Anhui Normal University, Wuhu 241000, China
E-mail: [email protected]
Search for more papers by this authorLuis Crovetto
Department of Physical Chemistry, Faculty of Pharmacy, University of Granada, Campus Cartuja, 18071 Granada, Spain
Search for more papers by this authorJuan A. González-Vera
Department of Physical Chemistry, Faculty of Pharmacy, University of Granada, Campus Cartuja, 18071 Granada, Spain
Search for more papers by this authorEva M. Talavera
Department of Physical Chemistry, Faculty of Pharmacy, University of Granada, Campus Cartuja, 18071 Granada, Spain
Search for more papers by this authorJose M. Alvarez-Pez
Department of Physical Chemistry, Faculty of Pharmacy, University of Granada, Campus Cartuja, 18071 Granada, Spain
Search for more papers by this authorCorresponding Author
Noël Boens
Department of Chemistry, KU Leuven (Katholieke Universiteit Leuven), Celestijnenlaan 200f, 3001 Leuven, Belgium
The Key Laboratory of Functional Molecular Solids, Ministry of Education, School of Chemistry and Materials Science, Anhui Normal University, Wuhu 241000, China
E-mail: [email protected]
Search for more papers by this authorCorresponding Author
María Jose Ruedas-Rama
Department of Physical Chemistry, Faculty of Pharmacy, University of Granada, Campus Cartuja, 18071 Granada, Spain
The Key Laboratory of Functional Molecular Solids, Ministry of Education, School of Chemistry and Materials Science, Anhui Normal University, Wuhu 241000, China
E-mail: [email protected]
Search for more papers by this authorConsuelo Ripoll
Department of Physical Chemistry, Faculty of Pharmacy, University of Granada, Campus Cartuja, 18071 Granada, Spain
Search for more papers by this authorCheng Cheng
The Key Laboratory of Functional Molecular Solids, Ministry of Education, School of Chemistry and Materials Science, Anhui Normal University, 241000 Wuhu, China
Search for more papers by this authorEmilio Garcia-Fernandez
Department of Physical Chemistry, Faculty of Pharmacy, University of Granada, Campus Cartuja, 18071 Granada, Spain
Search for more papers by this authorJin Li
The Key Laboratory of Functional Molecular Solids, Ministry of Education, School of Chemistry and Materials Science, Anhui Normal University, 241000 Wuhu, China
Search for more papers by this authorAngel Orte
Department of Physical Chemistry, Faculty of Pharmacy, University of Granada, Campus Cartuja, 18071 Granada, Spain
Search for more papers by this authorHainam Do
Department of Chemical and Environmental Engineering, University of Nottingham Ningbo China, 199 Taikang East Road, 315100 Ningbo, China
Search for more papers by this authorCorresponding Author
Lijuan Jiao
The Key Laboratory of Functional Molecular Solids, Ministry of Education, School of Chemistry and Materials Science, Anhui Normal University, 241000 Wuhu, China
The Key Laboratory of Functional Molecular Solids, Ministry of Education, School of Chemistry and Materials Science, Anhui Normal University, Wuhu 241000, China
E-mail: [email protected]
Search for more papers by this authorCorresponding Author
David Robinson
Department of Chemistry and Forensics, Nottingham Trent University, Clifton Lane, Nottingham, United Kingdom
The Key Laboratory of Functional Molecular Solids, Ministry of Education, School of Chemistry and Materials Science, Anhui Normal University, Wuhu 241000, China
E-mail: [email protected]
Search for more papers by this authorLuis Crovetto
Department of Physical Chemistry, Faculty of Pharmacy, University of Granada, Campus Cartuja, 18071 Granada, Spain
Search for more papers by this authorJuan A. González-Vera
Department of Physical Chemistry, Faculty of Pharmacy, University of Granada, Campus Cartuja, 18071 Granada, Spain
Search for more papers by this authorEva M. Talavera
Department of Physical Chemistry, Faculty of Pharmacy, University of Granada, Campus Cartuja, 18071 Granada, Spain
Search for more papers by this authorJose M. Alvarez-Pez
Department of Physical Chemistry, Faculty of Pharmacy, University of Granada, Campus Cartuja, 18071 Granada, Spain
Search for more papers by this authorCorresponding Author
Noël Boens
Department of Chemistry, KU Leuven (Katholieke Universiteit Leuven), Celestijnenlaan 200f, 3001 Leuven, Belgium
The Key Laboratory of Functional Molecular Solids, Ministry of Education, School of Chemistry and Materials Science, Anhui Normal University, Wuhu 241000, China
E-mail: [email protected]
Search for more papers by this authorCorresponding Author
María Jose Ruedas-Rama
Department of Physical Chemistry, Faculty of Pharmacy, University of Granada, Campus Cartuja, 18071 Granada, Spain
The Key Laboratory of Functional Molecular Solids, Ministry of Education, School of Chemistry and Materials Science, Anhui Normal University, Wuhu 241000, China
E-mail: [email protected]
Search for more papers by this authorGraphical Abstract
New BODIPY dyes substituted with a benzylamino group have been synthesized and characterized. The position of the benzylamino group has shown a significant influence on the spectroscopic and photophysical properties, which have been explored in different solvents. The dyes have been employed as probes in the fluorescence lifetime imaging of living cells, demonstrating their high potential for bioimaging.
Abstract
Three new boron dipyrromethene (BODIPY) dyes substituted with a benzylamino group at the 3-position have been synthesized from halogenated BODIPYs by nucleophilic substitution. The spectroscopic and photophysical properties have been explored in different solvents and have been compared with an analogous 8-benzylaminoBODIPY derivative. The position of the benzylamino group has a significant influence on the spectral band positions, fluorescence quantum yields, and fluorescence lifetimes. The 8-benzylaminoBODIPY emits in the blue range, whereas the 3-substituted shows green fluorescence. Additionally, the extension of the conjugation at the 5-position of 3-benzylaminoBODIPY produces a bathochromic shift of the absorption and emission spectra. The effect of solvents on their spectroscopic features has been investigated using the generalized Catalán solvent scales. Quantum-chemical calculations have been performed to assess the effect of the position of the substitution on the spectroscopic properties. Finally, the BODIPY dyes have been employed as probes in fluorescence lifetime imaging of living cells, demonstrating their high potential for bioimaging.
Supporting Information
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Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.
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