The solvatochromism of the 4-amino-,1,8-naphthalimide fluorophore is well established, with the wavelengths of maximum absorption and maximum emission shoswing a hypsochromic shift as the dielectric constant of the solvent decreases. We have synthesized a new naphthalimide dye with bulky 2,2,6,6-tetramethylpiperidine (TMP) groups at both the 4-, and N- positions. Computations reveal that this compound may form π-stacked complexes with planar aromatic species. In preliminary trials, we have observed this dye exhibits solvatochromic behavior that differs from what we expected on the basis of precedent. Herein, we report our findings of the solvatochromic behavior of this dye compared to a naphthalimide dye with sterically undemanding <i>n</i>-butyl substituents in the same positions, and results of our initial explorations of the formation of π complexes with various polycyclic arenes.

Solvatochromic behavior of a sterically hindered 4-aminonaphthalimide dye

2019 Spring National Meeting

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