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Synthesis, Photophysics, Electrochemistry and Electrogenerated Chemiluminescence of PEG-Modified BODIPY Dyes in Organic and Aqueous Solutions

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    Synthesis, Photophysics, Electrochemistry and Electrogenerated Chemiluminescence of PEG-Modified BODIPY Dyes in Organic and Aqueous Solutions
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    † Department of Chemistry and Biochemistry, University of Delaware, Newark, Delaware 19716, United States
    ‡ Department of Chemistry and Biochemistry, The University of Texas at Austin, Austin, Texas 78712, United States
    *E-mail: [email protected] (A.J.B.); [email protected] (J.R.).
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    The Journal of Physical Chemistry C

    Cite this: J. Phys. Chem. C 2013, 117, 11, 5599–5609
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    https://doi.org/10.1021/jp312166w
    Published March 7, 2013
    Copyright © 2013 American Chemical Society
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    Abstract

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    A set polyethylene glycol (PEG)-appended BODIPY architectures (BOPEG1–BOPEG3) have been prepared and studied in CH2Cl2, H2O:CH3CN (1:1) and aqueous solutions. BOPEG1 and BOPEG2 both contain a short PEG chain and differ in substitution about the BODIPY framework. BOPEG3 is comprised of a fully substituted BODIPY moiety linked to a PEG polymer that is roughly 13 units in length. The photophysics and electrochemical properties of these compounds have been thoroughly characterized in CH2Cl2 and aqueous CH3CN solutions. The behavior of BOPEG1–BOPEG3 correlates with established rules of BODIPY stability based on substitution about the BODIPY moiety. Electrogenerated chemiluminescence (ECL) for each of these compounds was also monitored. BOPEG1, which is unsubstituted at the 2- and 6-positions dimerized upon electrochemical oxidation while BOPEG2, which contains ethyl groups at the 2- and 6-positions, was much more robust and served as an excellent ECL luminophore. BOPEG3 is highly soluble in water due to the long PEG tether and demonstrated modest ECL activity in aqueous solutions using tri-n-propylamine (TPrA) as a coreactant. As such, BOPEG3 represents the first BODIPY derivative that has been shown to display ECL in water without the need for an organic cosolvent, and marks an important step in the development of BODIPY based ECL probes for various biosensing applications.

    Copyright © 2013 American Chemical Society

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    The Journal of Physical Chemistry C

    Cite this: J. Phys. Chem. C 2013, 117, 11, 5599–5609
    Click to copy citationCitation copied!
    https://doi.org/10.1021/jp312166w
    Published March 7, 2013
    Copyright © 2013 American Chemical Society
    Request reuse permissions

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