Synthesis and Optical and Redox Properties of Symmetric and Asymmetric BODIPYs

Authors

  • Prof. Inmaculada García-Moreno,

    1. Departamento de Sistemas de Baja Dimensionalidad, Superficies y Materia Condensada, Instituto de Química-Física “Rocasolano”, C.S.I.C. Serrano 119, 28006 Madrid (Spain)
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  • Lu Wang,

    1. State Key Laboratory of Fine Chemicals, Dalian University of Technology, West Campus, 2 Linggong Road, Dalian 116012 (China)
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  • Prof. Angel Costela,

    1. Departamento de Sistemas de Baja Dimensionalidad, Superficies y Materia Condensada, Instituto de Química-Física “Rocasolano”, C.S.I.C. Serrano 119, 28006 Madrid (Spain)
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  • Dr. Jorge Bañuelos,

    Corresponding author
    1. Departamento de Química Física, Universidad del País vasco (UPV-EHU), Aptdo. 644, 48080 Bilbao, Spain
    • Departamento de Química Física, Universidad del País vasco (UPV-EHU), Aptdo. 644, 48080 Bilbao, Spain
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  • Prof. Iñigo López Arbeloa,

    1. Departamento de Química Física, Universidad del País vasco (UPV-EHU), Aptdo. 644, 48080 Bilbao, Spain
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  • Prof. Yi Xiao

    Corresponding author
    1. State Key Laboratory of Fine Chemicals, Dalian University of Technology, West Campus, 2 Linggong Road, Dalian 116012 (China)
    • State Key Laboratory of Fine Chemicals, Dalian University of Technology, West Campus, 2 Linggong Road, Dalian 116012 (China)
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Abstract

Herein, we present the synthetic route and the photophysical, electrochemical as well as laser properties of novel red-emitting boron-dipyrromethenes (BODIPYs) bearing arylethyne moieties. Such functionality is added along the main axis of the chromophore leading to single- and double-substituted derivatives. The relationship between the dye structure and the lasing properties is studied in detail with the help of the photophysical and electrochemical properties as well as quantum mechanical simulations. The asymmetric substitution of the parent dye induces inhomogeneities in the charge distribution, which leads to an overall loss of the fluorescence capacity, mainly in polar media. Such non-radiative deactivation processes can be softened by decreasing the electron-donor ability of the substituent or even avoided by symmetrical substitution. Thus, grafting of the arylethyne moieties at the longitudinal axis of the indacene core results in an effective strategy to develop red-edge BODIPYs with highly efficient and photostable laser emission.

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