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Donor-disubstituted 2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-diones.

Authors: Podlesný Jan | Bureš Filip

Year: 2014

Type of publication: ostatní - přednáška nebo poster

Page from-to: nestránkováno

Titles:

Language	Name	Abstract	Keywords
eng	Donor-disubstituted 2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-diones.	Diketopyrrolopyrroles (DPP) are well-known pigments and dyes that found widespread applications especially in textile and car industry. More recently, the bicyclic lactam 2,5 dihydropyrrolo[3,4-c]pyrrole-1,4-dione has also been recognized as a  conjugated scaffold with electron-accepting properties suitable for the construction of organic materials. These materials were applied in a variety of (opto)electronic devices such as OFETs, OLEDs and DSSCs. The most widely used synthetic pathway leading to DPP core involves the reaction of (hetero)aromatic nitriles with succinates in the presence of t-amyl alcoholate. In this way, 3,6-disubstituted derivatives are generally obtained. When properly substituted at these two positions with electron-donors, the DPP derivative represents quadrupolar push-pull-push or D--A--D system with two peripheral donors and central DPP acceptor. In such molecules, intramolecular charge-transfer (ICT) from the donors to the acceptors occurs. Thus, the peripheral substituents at the positions 3 and 6 can be used for the fine property tuning. Electronic properties such as position of the longest-wavelength absorption maxima, electrochemical behaviour and respective HOMO-LUMO gap can be tailored in this way. The synthesis and basic properties of eight new DPP derivatives bearing peripheral donors such as methoxy, N,N dimethylamino, thiophene and ferrocene will be discussed.	diketopyrrolopyrrole, push-pull-push system, thiophene, ferocene, cross-coupling