Journal of Organic Chemistry
Journal of Organic Chemistry
5 years ago

From Highly Fluorescent Donors to Strongly Absorbing Acceptors: The Tunable Properties of Fluorubines

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

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b00676

DOI: 10.1021/acs.joc.7b00676

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