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Issue 5, 2016
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Modulation of band gap and p- versus n-semiconductor character of ADA dyes by core and acceptor group variation

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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

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Publication details

The article was received on 30 Jan 2016, accepted on 19 Feb 2016 and first published on 19 Feb 2016


Article type: Research Article
DOI: 10.1039/C6QO00046K
Citation: Org. Chem. Front., 2016,3, 545-555
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    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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