Issue 5, 2016

Modulation of band gap and p- versus n-semiconductor character of ADA dyes by core and acceptor group variation

Abstract

A series of ADA dyes was synthesized by Knoevenagel condensation reactions between dialdehydes of the electron-rich dithienopyrrole (DTP), cyclopentadithiophene (CPDT), carbazole (CAR) and fluorene (FL) moieties and the electron-poor CH-acidic indandione (IND) or 1,1-dicyanomethylene-3-indanone (DCIND) units, respectively. The UV/vis absorption spectra of the dyes cover a wide range of the visible spectrum from 450 to almost 700 nm in solution. Likewise, owing to differently balanced donor and acceptor strengths they may be applicable either as p- or n-type organic semiconductor materials in transistor and solar cell devices. As a proof-of-concept for dye vacuum-deposited organic thin film transistors (OTFTs) with either hole or electron mobilities of ∼0.1 cm2 V−1 s−1 depending on the HOMO/LUMO levels could be demonstrated.

Graphical abstract: Modulation of band gap and p- versus n-semiconductor character of ADA dyes by core and acceptor group variation

Supplementary files

Article information

Article type
Research Article
Submitted
30 Jan 2016
Accepted
19 Feb 2016
First published
19 Feb 2016

Org. Chem. Front., 2016,3, 545-555

Modulation of band gap and p- versus n-semiconductor character of ADA dyes by core and acceptor group variation

A. Nowak-Król, R. Wagener, F. Kraus, A. Mishra, P. Bäuerle and F. Würthner, Org. Chem. Front., 2016, 3, 545 DOI: 10.1039/C6QO00046K

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