TY - JOUR
T1 - Synthesis, Optical and Electrochemical Properties of Isomeric Dibenzophenanthroline Derivatives
AU - Ghosh, Animesh
AU - Li, Tianjiao
AU - Ni, Wenjun
AU - Wu, Tong
AU - Liang, Caihong
AU - Budanovic, Maja
AU - Morris, Samuel A.
AU - Klein, Maciej
AU - Webster, Richard D.
AU - Gurzadyan, Gagik G.
AU - Grimsdale, Andrew C.
N1 - Publisher Copyright:
© 2021 Wiley-VCH GmbH
PY - 2022/1
Y1 - 2022/1
N2 - Acid-catalysed Friedländer cyclization of 2-aminobenzophenones with 1,2-, 1,3-, and 1,4-cyclohexadiones, followed by aromatization, has been used to prepare dibenzophenanthrolines (DBPs) containing 1,10-, 1,7- and 4,7-phenanthroline units, whose optoelectronic properties have been compared. The LUMO energies for all isomers were similar but the 4,7-isomers possessed significantly higher HOMOs than the other isomers, resulting in them having smaller HOMO-LUMO energy gaps. Compared with 1,10-DBP isomers, the emission of 1,7-DBPs is strongly quenched due to efficient charge transfer. The 4,7-DBP isomers show strongly enhanced photoluminescence due to excimer formation but appear to be less photostable due to their higher HOMO levels. Bis(phenylethynyl)-substituted derivatives demonstrated improved solubility and stronger luminescence properties than their unsubstituted analogues.
AB - Acid-catalysed Friedländer cyclization of 2-aminobenzophenones with 1,2-, 1,3-, and 1,4-cyclohexadiones, followed by aromatization, has been used to prepare dibenzophenanthrolines (DBPs) containing 1,10-, 1,7- and 4,7-phenanthroline units, whose optoelectronic properties have been compared. The LUMO energies for all isomers were similar but the 4,7-isomers possessed significantly higher HOMOs than the other isomers, resulting in them having smaller HOMO-LUMO energy gaps. Compared with 1,10-DBP isomers, the emission of 1,7-DBPs is strongly quenched due to efficient charge transfer. The 4,7-DBP isomers show strongly enhanced photoluminescence due to excimer formation but appear to be less photostable due to their higher HOMO levels. Bis(phenylethynyl)-substituted derivatives demonstrated improved solubility and stronger luminescence properties than their unsubstituted analogues.
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U2 - 10.1002/ajoc.202100670
DO - 10.1002/ajoc.202100670
M3 - Article
AN - SCOPUS:85120780811
SN - 2193-5807
VL - 11
JO - Asian Journal of Organic Chemistry
JF - Asian Journal of Organic Chemistry
IS - 1
M1 - e202100670
ER -