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 Жел. 2018
Accepted
20 Нау. 2019
First published
21 Нау. 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

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements