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Bandgap Engineering in π-Extended Pyrroles. A Modular Approach to Electron-Deficient Chromophores with Multi-Redox Activity

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    Bandgap Engineering in π-Extended Pyrroles. A Modular Approach to Electron-Deficient Chromophores with Multi-Redox Activity
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    † Wydział Chemii, Uniwersytet Wrocławski, ul. F. Joliot-Curie 14, 50-383 Wrocław, Poland
    ‡ Wrocławskie Centrum Badań EIT+, ul. Stabłowicka 147, 54-066 Wrocław, Poland
    *[email protected]
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    Cite this: J. Am. Chem. Soc. 2016, 138, 35, 11390–11398
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    https://doi.org/10.1021/jacs.6b07826
    Published August 17, 2016
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    Abstract

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    A family of bandgap-tunable pyrroles structurally related to rylene dyes was computationally designed and prepared using robust, easily scalable chemistry. These pyrroles show highly variable fluorescence properties and can be used as building blocks for the synthesis of electron-deficient oligopyrroles. The latter application is demonstrated through the development of π-extended porphyrins containing naphthalenediamide or naphthalenediimide units. These new macrocycles exhibit simultaneously tunable visible and near-IR absorptions, an ability to accept up to 8 electrons via electrochemical reduction, and high internal molecular free volumes. When chemically reduced under inert conditions, the most electron-deficient of these macrocycles revealed reversible formation of eight charged states, characterized by remarkably red-shifted optical absorptions, extending beyond 2200 nm. Such features make these oligopyrroles of interest as functional chromophores, charge-storage materials, and tectons for crystal engineering.

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    Cite this: J. Am. Chem. Soc. 2016, 138, 35, 11390–11398
    Click to copy citationCitation copied!
    https://doi.org/10.1021/jacs.6b07826
    Published August 17, 2016
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