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Issue 34, 2017
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Orthogonal 4,10 and 6,12 substitution of dibenzo[def,mno]chrysene polycyclic aromatic small molecules

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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.

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

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Publication details

The article was received on 07 Jun 2017, accepted on 29 Jun 2017 and first published on 14 Jul 2017


Article type: Paper
DOI: 10.1039/C7TC02528A
Citation: J. Mater. Chem. C, 2017,5, 8723-8733
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    Orthogonal 4,10 and 6,12 substitution of dibenzo[def,mno]chrysene polycyclic aromatic small molecules

    U. Koldemir, J. S. Tinkham, R. Johnson, B. Lim, H. A. Yemam, K. J. Gagnon, S. Parkin and A. Sellinger, J. Mater. Chem. C, 2017, 5, 8723
    DOI: 10.1039/C7TC02528A

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