Issue 17, 2019

Bis(tercarbazole) pyrene and tetrahydropyrene derivatives: photophysical and electrochemical properties, theoretical modeling, and OLEDs

Abstract

2,7-Bis(3,3′′,6,6′′-tetra(tert-butyl)-9′H-9,3′:6′,9′′-tercarbazol-9-yl)-4,5,9,10-tetrahydropyrene (3) and 2,7-bis(3,3′′,6,6′′-tetra(tert-butyl)-9′H-9,3′:6′,9′′-tercarbazol-9-yl)pyrene (4), along with a model compound, 3,3′′,6,6′′-tetra(tert-butyl)-9′-(4-(tert-butyl)phenyl)-9′H-9,3′:6′,9′′-tercarbazole (6), have been synthesized using microwave-assisted palladium-catalyzed coupling and compared to analogous 3,6-di(tert-butyl)carbazol-9-yl species (1, 2, and 5). Time-dependent density functional theory (TDDFT) calculations reveal absorption with quadrupolar (ter)carbazole-to-bridge CT character for 1–4. Compound 4 is unusual in showing dual fluorescence in a number of solvents; the longer wavelength feature of which is markedly more solvatochromic than the bands of the other compounds. Following the observed three oxidations on the TCz model compound 6, compounds 3 and 4 can be electrochemically reversibly oxidized to hexacations with four oxidation and three oxidation steps in a 2 : 2 : 1 : 1 and a 2 : 2 : 2 current ratio, respectively. Tercarbazole derivatives 3 and 4 have been used as the emissive layers of simple solution-processed few-layer organic light-emitting diodes.

Graphical abstract: Bis(tercarbazole) pyrene and tetrahydropyrene derivatives: photophysical and electrochemical properties, theoretical modeling, and OLEDs

Supplementary files

Article information

Article type
Paper
Submitted
12 Kax 2018
Accepted
20 Cig 2019
First published
21 Cig 2019

J. Mater. Chem. C, 2019,7, 5009-5018

Author version available

Bis(tercarbazole) pyrene and tetrahydropyrene derivatives: photophysical and electrochemical properties, theoretical modeling, and OLEDs

B. R. Kaafarani, T. H. El-Assaad, W. A. Smith, S. M. Ryno, F. Hermerschmidt, J. Lyons, D. Patra, B. Wex, E. J. W. List-Kratochvil, C. Risko, S. Barlow and S. R. Marder, J. Mater. Chem. C, 2019, 7, 5009 DOI: 10.1039/C8TC06266H

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