N,N-Bis(trimethylsilyl)-9-aminoanthracene (Si9AA) was synthesized by deprotonation of
9-aminoanthracne (9AA) with n-BuLi followed by the addition of trimethylsilyl chloride (TMSCl).
Under ultraviolet, Si9AA showed blue fluorescence originated from the anthracene skeleton due to orthogonal
relation between anthracene skeleton and bis(trimethylsilyl)amino group, which was determined
by X-ray crystallographic analysis, while 9AA, in which conjugation exists between the anthracene
and the amino group, showed green fluorescence. In a THF solution, Si9AA was converted to
9AA by desilylation of bis(trimethylsilyl)amino group with fluoride ion, which was contained in tetrabutylammonium
fluoride (TBAF) or KF-18-crown-6 complex, resulting in fluorescence color
change from blue to green. Si9AA was found to utilize as a sensor to detect fluoride ion in THF solution
or on a thin layer chromatography (TLC) via the fluorescence color change without any metals,
regarding a metal free fluorescence fluoride sensor in green chemistry.