Tunable full-color dual-state (solution and solid) emission of push–pull molecules containing the 1-pyrindane moiety

• Anastasia I. Ershova,
• Sergey V. Fedoseev,
• Konstantin V. Lipin,
• Mikhail Yu. Ievlev,
• Oleg E. Nasakin and
• Oleg V. Ershov

Beilstein J. Org. Chem. 2024, 20, 3016–3025, doi:10.3762/bjoc.20.251

• pyrindane – (E)-7-arylmethylene-2-chloro-6,7-dihydro-5H-cyclopenta[b]pyridine-3,4-dicarbonitriles – was developed. Tunable full-color emission was achieved for the synthesized push–pull molecules, solely by changing donor groups while keeping both the conjugated system and acceptor part of the molecule

• unchanged. This represents a rare approach for the design of such fluorophores. Arylidene derivatives of pyrindane were found to be efficient fluorescent dyes showing a moderate to high emission quantum yield. The push–pull molecules were also characterized by a dual-state emission (in solution and in the

• acid both in solution and in the solid state. Keywords: dual-state emission; full-color emission; nitriles; push–pull molecules; pyrindane; stilbazole; Introduction Over the past decades, heteroaromatic push–pull molecules have attracted great attention due to their widespread use in materials

Structure–property relationships and third-order nonlinearities in diketopyrrolopyrrole based D–π–A–π–D molecules

• Jan Podlesný,
• Lenka Dokládalová,
• Oldřich Pytela,
• Adam Urbanec,
• Milan Klikar,
• Numan Almonasy,
• Tomáš Mikysek,
• Jaroslav Jedryka,
• Iwan V. Kityk and
• Filip Bureš

Beilstein J. Org. Chem. 2017, 13, 2374–2384, doi:10.3762/bjoc.13.235

• investigated for DPP derivatives. The most common applications of organic molecules with THG activity are directed towards all-optical signal processing and optical imaging [30][31]. Hence, as a continuation of our research activity on incorporating heteroaromatic moieties in push–pull molecules [9][10], we

Syntheses of 3,4- and 1,4-dihydroquinazolines from 2-aminobenzylamine

• Jimena E. Díaz,
• Silvia Ranieri,
• Nadia Gruber and
• Liliana R. Orelli

Beilstein J. Org. Chem. 2017, 13, 1470–1477, doi:10.3762/bjoc.13.145

• analogous reaction had been previously reported for 3,4-dihydroquinazolines upon exposure to air (Scheme 3, (b)) [19][24][40][66]. The fact that quinazolin-4(1H)-ones 6, which are fully conjugated push–pull molecules, are more resonance stabilized than their isomeric counterparts quinazolin-4(3H)-ones 7

Solution processable diketopyrrolopyrrole (DPP) cored small molecules with BODIPY end groups as novel donors for organic solar cells

• Diego Cortizo-Lacalle,
• Calvyn T. Howells,
• Upendra K. Pandey,
• Joseph Cameron,
• Neil J. Findlay,
• Anto Regis Inigo,
• Tell Tuttle,
• Peter J. Skabara and
• Ifor D. W. Samuel

Beilstein J. Org. Chem. 2014, 10, 2683–2695, doi:10.3762/bjoc.10.283

• derivatives (e.g., selenophene) [20][21][22][23], often in combination with other heterocyclic units; the best performing systems are push–pull molecules or dyes [14]. In the last few years the diketopyrrolopyrrole (DPP, 1, Figure 1) core has been widely incorporated in conjugated polymers for both OPVs and

Imidazole as a parent π-conjugated backbone in charge-transfer chromophores

• Jiří Kulhánek and
• Filip Bureš

Beilstein J. Org. Chem. 2012, 8, 25–49, doi:10.3762/bjoc.8.4

• on alkoxysilanes [105][106]. This new material is to be applied as an electro-optic modulator. Our synthetic efforts in the field of 4,5-dicyanoimidazole-derived chromophores began with the initial set of push–pull molecules 88–93 (Figure 16; [30]). Chromophores 88–93 were synthesized by Suzuki