Synthesis and molecular properties of methoxy-substituted diindolo[3,2-b:2′,3′-h]carbazoles for organic electronics obtained by a consecutive twofold Suzuki and twofold Cadogan reaction

Abstract

A set of methoxy-substituted diindolo [3,2-b:2 0 ,3 0 -h]carbazoles has been synthesized by twofold SuzukiMiyaura, Cadogan and N-alkylation reactions starting from N-hexyl-2,7-dibromo-3,6-dinitro carbazole.Microwave accelerated reactions ensure a rapid straightforward and step-ecomomic assembly of the

Triggering Thermally Activated Delayed Fluorescence by Managing the Heteroatom in Donor Scaffolds: Intriguing Photophysical and Electroluminescence Properties

“…The synthetic routes used to synthesize the target materials are illustrated in Scheme . Key intermediates, such as 10 H ‐benzofuro[3,2‐b]indole (BFI) and 10 H ‐benzo[4,5]thieno[3,2‐ b ]indole (BTI), were synthesized according to literature procedures . The aforementioned intermediates were treated with 5‐(4,6‐diphenyl‐1,3,5‐triazin‐2‐yl)‐2‐fluorobenzonitrile under cesium carbonate mediated N ‐arylation reaction conditions to give BFICNTrz and BTICNTrz in good yields.…”

“…Key intermediates, such as 10H-benzofuro[3,2b]indole (BFI) and 10H-benzo[4,5]thieno[3,2-b]indole( BTI), were synthesized according to literature procedures. [15] The aforementioned intermediates were treated with 5-(4,6-diphenyl-1,3,5-triazin-2-yl)-2-fluorobenzonitrile under cesium carbonate mediated N-arylation reaction conditions to give BFICNTrz and BTICNTrz in good yields. The chemical structures of the compounds were confirmed by using 1 Ha nd 13 CNMR spectroscopy and MS analysis.…”

“…Inspiredb yt he above discussions, we developed two new green TADF emitters, 2-(10H-benzofuro[3,2-b]indol-10-yl)-5-(4,6diphenyl-1,3,5-triazin-2-yl)benzonitrile (BFICNTrz)a nd 2-(10Hbenzo [4,5]thieno[3,2-b]indol-10-yl)-5-(4,6-diphenyl-1,3,5-triazin-2-yl)benzonitrile (BTICNTrz), with 10H-benzofuro[3,2-b]indole (BFI) and 10H-benzo[4,5]thieno[3,2-b]indole (BTI) donors and an aryltriazine acceptor.A lthough somes ynthetic syntheses have been achieved for BTI and BFI in the literature, their potential as electron donors in functional materials for electroluminescent applicationsh as not been explored to datet oo ur knowledge. [15] To this end, we explored their potential as donors in TADF emitters for OLED applications. The effect of oxygen and sulfur heteroatoms in the donor scaffold on the physicochemical and electroluminescence properties of the compounds was studied in detail.…”

1,4,9,12-Tetramethoxy-14-octyl-5,8-dihydrodiindolo[3,2-b;2′,3′-h]carbazole with an unknown solvent

“…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.…”

Hybrid nickel-free graphene/porphyrin rings for photodegradation of emerging pollutants in water

“…S6 †) we measured the optical bandgap (E g ) as E g ¼ 2.2 eV and thus we estimated the HOMO energy level as E HOMO ¼ E LUMO À E g , nding the eqn (1) E HOMO ¼ À6.4 AE 0.2 eV. [49][50][51] To our knowledge, this is the rst time that HOMO and LUMO energy levels of cyclic porphyrins-based copolyformal are measured by CV.…”