Two-Step Synthetic Route toward Asymmetric and Symmetric Boron Dipyrromethenes: Synthesis, Optical Properties, and Electrochemistry

Two-Step Synthetic Route toward Asymmetric and Symmetric Boron Dipyrromethenes: Synthesis, Optical Properties, and Electrochemistry

    Presenter(s)

    Michael A Coladipietro

    Description

    A two-step synthetic route toward BODIPY dyes is accomplished by reaction of the readily available naphtho[1,2-c]pyrrole with various aldehydes followed by coordination of BF2. Synthesis of the dipyrromethene is achieved by simply heating the pyrrole and aldehyde at moderate temperatures for less than 30 min. In addition to the absence of solvent this reaction does not require an acid catalyst or an oxidizing agent to achieve the dipyrromethene. Investigation of various aldehydes by this method suggests that the choice of aldehyde plays a role in the formation of either symmetric or asymmetric BODIPYs. The dyes have exceptionally high molar absorptivities (> 100000 m–1 cm–1) in the far visible region of the electromagnetic spectrum with intense emission and high quantum efficiency.

    Publication Date

    4-5-2017

    Project Designation

    Honors Thesis - Undergraduate

    Primary Advisor

    Shawn M. Swavey

    Primary Advisor's Department

    Chemistry

    Keywords

    Stander Symposium project

    Two-Step Synthetic Route toward Asymmetric and Symmetric Boron Dipyrromethenes: Synthesis, Optical Properties, and Electrochemistry

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