Heteroaromatic polycyclic compounds are particularly useful because of their simultaneous tunability of fluorescence color and intensity, making them well suited as sensors and fluorophores. The incorporation of various substituents such as electron donating and electron withdrawing moieties into polycyclic aromatic hydrocarbons has been of great interest because they induce modification of the electronic transitions energies in the non-flexible π-systems. We have designed, synthesized and investigated a series of polycyclic azaborine chromophores as easily tunable high-luminescent organic materials. The substituent effects on the polycyclic azaborine chromophores were investigated by the addition of electron withdrawing and electron donating moieties to the left and right sides of the core of the chromophore to define the role of the electron donating and electron withdrawing substituents on their HOMOs and LUMOs and to aid in understanding fluorescence tunability. The addition of electron withdrawing substituents to the left side of the polycyclic azaborine chromophores red-shifted the fluorescence by 130 nm from 490 nm to 620 nm with a 200 nm Stokes shift. However, the addition of electron withdrawing substituents to the right side of the polycyclic azaborine chromophores blue-shifted the fluorescence. The incorporation of electron donating moieties to the right side of the polycyclic azaborine chromophores red-shifted the fluorescence by 82 nm from 416 nm to 498 nm with a 105 nm Stokes shift. Conversely, the addition of electron donating moieties to the left side of the polycyclic azaborine chromophores blue-shifted the fluorescence of the polycyclic azaborine chromophores. Based on our findings, we have shown that we can tune the fluorescence of the azaborine chromophores by the incorporation of substituents to the right and left sides of the core structure of the chromophore.

Tunable highly fluorescent polycyclic azaborine chromophores: Applications in organic materials

253rd National Meeting (2017)

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