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

Unsal Koldemir, Jonathan S. Tinkham, Robert Johnson, Bogyu Lim, Henok A. Yemam, Kevin J. Gagnon, Sean Parkin, Alan Sellinger

Research output: Contribution to journalArticlepeer-review

11 Scopus citations

Abstract

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.
Original languageEnglish (US)
Pages (from-to)8723-8733
Number of pages11
JournalJ. Mater. Chem. C
Volume5
Issue number34
DOIs
StatePublished - 2017
Externally publishedYes

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