Azulene (1) is an aromatic hydrocarbon with the same molecular formula as naphthalene, but unlike the colorless naphthalene, azulene has a brilliant royal blue color. The color of azulene changes dramatically when the ring system is substituted, and when it is exposed to strong acids. With a series of reactions, we intend to transform azulene into a chelating agent. Hopefully, the coordination complexes that N-azuleneiminodiacetic acid (4) forms with various metals ions will produce a variety of colors. Our synthesis involves nitrating 1 with tetranitomethane (TNM) to form 2, reduction of �NO2 to �NH2 3, and SN2 addition of chloroacetic acid 4. The first two intermediates (2,3) have been identified using UV-Vis spectroscopy and 1H-NMR spectroscopy. Further work is required to purify the final product.
