TY - JOUR
T1 - Orthogonal 4,10 and 6,12 substitution of dibenzo[def,mno]chrysene polycyclic aromatic small molecules
AU - Koldemir, Unsal
AU - Tinkham, Jonathan S.
AU - Johnson, Robert
AU - Lim, Bogyu
AU - Yemam, Henok A.
AU - Gagnon, Kevin J.
AU - Parkin, Sean
AU - Sellinger, Alan
N1 - Publisher Copyright:
© 2017 The Royal Society of Chemistry.
PY - 2017
Y1 - 2017
N2 - 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.
AB - 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.
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U2 - 10.1039/c7tc02528a
DO - 10.1039/c7tc02528a
M3 - Article
AN - SCOPUS:85028752374
SN - 2050-7534
VL - 5
SP - 8723
EP - 8733
JO - Journal of Materials Chemistry C
JF - Journal of Materials Chemistry C
IS - 34
ER -