Abstract
AbstractAcridine derivatives are widely used as antiseptics, disinfectants, antibiotics, and fluorescent dyes as well as a subunit of optical sensor molecules of various analytical applications. We reported here the synthesis of several new 9‐substituted‐4,5‐dimethoxyacridine derivatives (9‐bromo‐, 9‐(p‐methylphenyl)‐, 9‐(p‐benzyloxyphenyl)‐, 9‐azido‐, 9‐phenyltriazole‐, 9‐[(trimethylsilyl)ethynyl]‐, 9‐nitrile‐) as potential multifunctionalizable fluorescent precursors of sensor molecules, indicators or dyes including optimized procedures for preparation of 9‐haloacridines and their cross‐coupling reactions. Improved stability of several new compounds could be achieved by the synthetic modification at position 9 of the acridine unit compared to their unsubstituted acridine analogs. The basic spectroscopic characteristics of these useful intermediates were also determined. The new fluorescent compounds showed promising photochemical properties for optochemical‐based applications in the future. The extremely large Stokes‐shifts (above 15500 cm−1) should especially be emphasized. Moreover, the effects of the substituents at position 9 of the acridine unit on fluorescence signaling were studied by the examples of new precursors and their macrocyclic derivatives as known optical sensor molecules. Some interesting relationships between quantum yield and structural features were reported.
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