SYNTHESIS AND PROPERTIES OF FRINGELITE-D -PHENANTHO[1,10,9,8,O,P,Q,R,A]PERYLENE-7,14-DIONE)

Fringelite D was synthesized from 1,3,6,8-tetramethoxyanthracen-9-ol v ia two different efficient routes. The first one involved demethylatio n and subsequent dimerization. The other one started with dimerization to yield octamethylfringelite D and subsequent demethylation. The sta rting material was prepared in four steps from commercially available educts, the key step being a benzamide ortho-lithiation. The spectrosc opic properties of fringelite D were measured and are discussed. The d issociation, deprotonation, and protonation equilibria of fringelite D were characterized by their respective pK values in ground and excite d states and compared with those of hypericin. Homo- and heteroassocia tion properties of fringelite D were found to be similar to those of h ypericin.