From Highly Fluorescent Donors to Strongly Absorbing Acceptors

The Tunable Properties of Fluorubines

Dominique Mario Gampe, Stefan Schramm, Steffen Ziemann, Matthias Westerhausen, Helmar Görls, Pance Naumov, Rainer Beckert

    Research output: Contribution to journalArticle

    Abstract

    The synthesis and characterization of three novel fluorubine derivatives is reported via three to four simple reaction steps with isolatable intermediates. The functional dyes are characterized by their strong absorption peaks in the visible region and their high fluorescence quantum yields. A significant and useful feature is that the properties can be tuned over a wide range by changing the pH. Transformation of the dyes into protonated amidinium salts leads to narrower band gaps and to drastically lower LUMO energies. Further reduction of the pH results in the doubly protonated species with a high electron-deficiency and LUMO energies of -4.8 eV, bathochromic shifts, and a strong intensity increase of up to ϵ = 120 000 M-1 cm-1.

    Original languageEnglish (US)
    Pages (from-to)6153-6162
    Number of pages10
    JournalJournal of Organic Chemistry
    Volume82
    Issue number12
    DOIs
    StatePublished - Jun 16 2017

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    Coloring Agents
    Quantum yield
    Energy gap
    Salts
    Fluorescence
    Derivatives
    Electrons
    dihydro-5,6,7,12,13,14-hexaazapentacene

    ASJC Scopus subject areas

    • Organic Chemistry

    Cite this

    Gampe, D. M., Schramm, S., Ziemann, S., Westerhausen, M., Görls, H., Naumov, P., & Beckert, R. (2017). From Highly Fluorescent Donors to Strongly Absorbing Acceptors: The Tunable Properties of Fluorubines. Journal of Organic Chemistry, 82(12), 6153-6162. https://doi.org/10.1021/acs.joc.7b00676

    From Highly Fluorescent Donors to Strongly Absorbing Acceptors : The Tunable Properties of Fluorubines. / Gampe, Dominique Mario; Schramm, Stefan; Ziemann, Steffen; Westerhausen, Matthias; Görls, Helmar; Naumov, Pance; Beckert, Rainer.

    In: Journal of Organic Chemistry, Vol. 82, No. 12, 16.06.2017, p. 6153-6162.

    Research output: Contribution to journalArticle

    Gampe, DM, Schramm, S, Ziemann, S, Westerhausen, M, Görls, H, Naumov, P & Beckert, R 2017, 'From Highly Fluorescent Donors to Strongly Absorbing Acceptors: The Tunable Properties of Fluorubines', Journal of Organic Chemistry, vol. 82, no. 12, pp. 6153-6162. https://doi.org/10.1021/acs.joc.7b00676
    Gampe, Dominique Mario ; Schramm, Stefan ; Ziemann, Steffen ; Westerhausen, Matthias ; Görls, Helmar ; Naumov, Pance ; Beckert, Rainer. / From Highly Fluorescent Donors to Strongly Absorbing Acceptors : The Tunable Properties of Fluorubines. In: Journal of Organic Chemistry. 2017 ; Vol. 82, No. 12. pp. 6153-6162.
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