Orthogonal 4, 10 and 6, 12 substitution of dibenzo [def, mno] chrysene polycyclic aromatic small molecules

A series of new polycyclic aromatic hydrocarbon compounds based on (4,10-disubstituted-dibenzo [def,mno] chrysene-6,12-dione) and 4,10 di-substituted 6,12-bis (triisopropylsilylethynyl) dibenzo [def,mno] chrysene are reported with tunable electronic properties through varied molecular architecture. Starting with an inexpensive commercially available textile dye known as Vat Orange #3, (4,10-dibromo-dibenzo [def,mno] chrysene-6,12-dione) we extended the conjugation at the 4- and 10-positions by the attachment of both electron rich and deficient hexylvinylphthalimide, thiophene, hexylthiophene, triphenylamine, and hexylbithiophene aromatic groups, and studied the resultant optoelectronic properties. By applying various synthetic metal-catalyzed reactions, soluble dibenzo[def,mno]chrysene and dibenzo [def,mno] chrysene-6,12-dione derivatives were achieved with optical edge band gaps between 2.30 eV and 1.65 eV.