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A joint experimental and theoretical study on the electro-optical properties of 1,6- and 1,7-fluorenyl disubstituted perylene diimide isomers

Abstract

Core substituted perylene diimides (PDI), obtained by introducing various functional groups into the perylenic bay positions, are well known as versatile materials for optoelectronic applications. The substitution of the perylene core affords mono-, di- and tri-substitutedderivatives, governed by the regioisomeric mixture of the 1,6- and 1,7-disubstituted PDIs. Most often, the disubstituted isomers are used as a mixture, because of difficult separation by conventional methods ortime consuming crystallization process. In this work, from the regioisomeric mixture of bis[9,9′-dioctylfluorenyl)]-N,N’-bis-(10-nonadecyl)-perylene-3,4,9,10-bis(dicarboximide), the 1,6- (PDI-F1) and 1,7- (PDI-F2) isomers have been easily isolated and separated by column chromatography and were subsequently characterized. The spectral features, electronic density distribution, the ground and excited state dipole moments of PDI-F1 have been examined and compared with PDI-F2. Several differences have been observed in the properties of the two PDI isomers. PDI-F1 absorption spectrum shows an unique broad band spanning from 450 nm to 640 nm, while PDI-F2 exhibits a lowest energy absorption at 570 nm and a strong band at 420 nm. The absorption and emission properties in different solvents has evidenced that although both regioisomers show dipole moment values of excited states higher than those of the corresponding ground states, the dipole moment variation upon excitation is different for each isomer. Cyclic voltammetry measurements revealed that PDI-F2 has stronger electron accepting ability, as evidenced by lower reduction potentials. Complementary density functional theory calculations are also reported in order to rationalize their electronic and optical properties.

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Publication details

The article was received on 09 Oct 2017, accepted on 02 Dec 2017 and first published on 04 Dec 2017


Article type: Paper
DOI: 10.1039/C7NJ03860G
Citation: New J. Chem., 2017, Accepted Manuscript
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    A joint experimental and theoretical study on the electro-optical properties of 1,6- and 1,7-fluorenyl disubstituted perylene diimide isomers

    E. Kozma, W. Mróz, A. Andicsová, V. Lukes, F. Galeotti, A. Siskova, M. Danko and M. Catellani, New J. Chem., 2017, Accepted Manuscript , DOI: 10.1039/C7NJ03860G

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