2016
DOI: 10.3390/molecules21060785
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Synthesis of Linearly Fused Benzodipyrrole Based Organic Materials

Abstract: Abstract:The objective of this review is to give an overview of the synthetic methods to prepare different indolo [3,2-b]carbazoles and similar systems with a potential use in electro-optical devices such as OLEDs (organic light emitting diode), OPVs (organic photovoltaic) and OFETs (organic field effect transistor). Some further modifications to the core units and their implications for specific applications are also discussed.

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Cited by 34 publications
(14 citation statements)
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“…Among the different synthetic routes (Vlasselaer & Dehaen, 2016), the twofold Cadogan reaction (Cadogan et al, 1965) is a very successful route to indolocarbazoles (Kistenmacher & Mü llen, 1992;Wrobel et al, 2013) and is also suitable for the preparation of higher oligomers (Srour et al, 2016). In a continuation of our studies on indolo-annulated heterocycles (Dassonneville et al, 2011;Nissen & Detert, 2011;Letessier & Detert, 2013), we present here the first X-ray structure of a linear diindolocarbazole (Fig.…”
Section: Structure Descriptionmentioning
confidence: 99%
“…Among the different synthetic routes (Vlasselaer & Dehaen, 2016), the twofold Cadogan reaction (Cadogan et al, 1965) is a very successful route to indolocarbazoles (Kistenmacher & Mü llen, 1992;Wrobel et al, 2013) and is also suitable for the preparation of higher oligomers (Srour et al, 2016). In a continuation of our studies on indolo-annulated heterocycles (Dassonneville et al, 2011;Nissen & Detert, 2011;Letessier & Detert, 2013), we present here the first X-ray structure of a linear diindolocarbazole (Fig.…”
Section: Structure Descriptionmentioning
confidence: 99%
“…Although other possible configurations also exist, these are rather rare and usually not incorporated in the “classical” indolocarbazole concept [36] . In particular, the chemistry of indolo[3,2‐ b ]carbazole has frequently been reported in the literature, [37–41] evidencing a quinoidal character for its ground state [42, 43] and an easy modulation of their properties by the insertion of functional groups [44–48] . However, the introduction of dicyanomethylene terminal groups, a well‐known strategy to stabilize diradical species, has not been explored so far in these materials.…”
Section: Introductionmentioning
confidence: 99%
“…Small‐molecule organic semiconductors are of interest for a variety of electronic devices, including organic thin‐film transistors (TFTs) [1] . Among the large number of molecular motifs that have been explored for the fabrication of organic p‐channel TFTs are the indolocarbazoles (ICZs) [2,3] . Indolocarbazoles are typically characterized by good solubility in common organic solvents and good air stability, which can be attributed to their low‐lying HOMO‐energy level.…”
Section: Introductionmentioning
confidence: 99%